Alkylene chain-containing silane compound

By using silane compounds with specific structures to form the surface treatment layer, the problems of high adhesion fingerprint recognition and insufficient friction durability in the prior art are solved, and the effects of low adhesion fingerprint recognition and high friction durability are achieved.

CN120344542APending Publication Date: 2025-07-18DAIKIN INDUSTRIES LTD
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Patent Information

Application Number
CN202380084934.5
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Priority Date
2022-12-26
Filing Date
2023-12-26
Publication Date
2025-07-18

AI Technical Summary

Technical Problem

When the conventional silane compounds form the surface treatment layer, there is a problem that the adhered fingerprint has high recognition and insufficient friction durability.

Method used

A silane compound with a specific structure includes a compound having a polar functional group such as an ester group or a vinyl, amino or halogen group at the end, and a surface treatment layer is formed by a surface treatment agent to improve the adhesion of fingerprint recognition and enhance friction durability.

Benefits of technology

The surface treatment layer with low attachment fingerprint recognition and high friction durability is achieved, which improves the use performance of the article.

✦ Generated by Eureka AI based on patent content.

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Abstract

[In the formula, R1 is R2-O-CO-, R2-COO-, CH2 = CH-, NHR3-, CR53-, CHR52-, CH2R5-or a halogen atom, R2 is a hydrogen atom or a C1-6 alkyl group, R3 is a hydrogen atom or a C1-6 alkyl group, R5 is a halogen atom, X1 is an alkylene group having 12 or more carbon atoms, X2 is a single bond or a 2-10 valent organic group, RSi is a monovalent group including a Si atom to which a hydroxyl group or a hydrolyzable group is bonded, alpha is an integer of 1-9, beta is an integer of 1-9, and n is an integer of 1-9. The sum of alpha and beta is equal to the valence of X2. ] A silane compound represented by formula (1). (R1-X1) a-X2-(RSi) beta (1)
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Description

Technical Field

[0001] The present invention relates to a silane compound containing an alkylene chain, and an article including a surface treatment layer containing the compound. Background Art

[0002] It is known that certain types of silane compounds can provide a surface treatment layer with low visibility of attached fingerprints when used for surface treatment of a substrate (Patent Document 1).

[0003] Prior Art Documents

[0004] Patent Documents

[0005] Patent Document 1: International Publication No. 2016 / 199908 Summary of the Invention

[0006] Technical Problem to be Solved by the Invention

[0007] An object of the present invention is to provide a compound capable of forming a surface treatment layer with low visibility of attached fingerprints and having high friction durability.

[0008] Technical Means for Solving the Technical Problem

[0009] The present invention includes the following aspects.

[0010] [1] A silane compound represented by the following formula (1).

[0011] (R 1 -X 1 ) α -X 2 -(R Si ) β (1)

[0012] [In the formula:

[0013] R 1 is R 2 -O-CO-, R 2 -COO-, R 2 -O-C(=O)-O-, R 2 -NR-CO-, R 2 -CO-NR-, R 2 -OCO-NR-, R 2 -NR 3 -COO-, R 2 -NR-CO-NR 3 -, CH2=CH-, NHR 3 -, CR 5 3-, CHR 5 2-, CH2R 5- or a halogen atom,

[0014] R 2 is a hydrogen atom, C 1-6 alkyl or a group of oxyalkylene having 1 to 30 carbon atoms,

[0015] R 3 is a hydrogen atom or C 1-6 alkyl,

[0016] R 5 is a halogen atom,

[0017] X 1 is an alkylene having 12 or more carbon atoms,

[0018] X 2 is a single bond or a 2- to 10-valent organic group,

[0019] R Si is a monovalent group containing a Si atom bonded with a hydroxyl group or a hydrolyzable group,

[0020] α is an integer from 1 to 9,

[0021] β is an integer from 1 to 9,

[0022] The sum of α and β is equal to the valence of X 2 .

[0023] [2] The silane compound as described in [1] above, wherein R 1 is R 2 -O-CO-, R 2 -O-C(=O)-O-, R 2 -NR-CO-, R 2 -CO-NR-, R 2 -OCO-NR-, R 2 -NR 3 -COO-, R 2 -NR-CO-NR 3 -, CH2=CH-, NH2- or a bromine atom,

[0024] R 2 is C 1-6 alkyl or a group of oxyalkylene having 1 to 30 carbon atoms,

[0025] R 3 is a hydrogen atom or C 1-6 alkyl.

[0026] [3] The silane compound as described in [1] or [2] above, wherein X 1 is C 12-36 alkylene.

[0027] [4] The silane compound according to any one of [1] to [3] above, wherein X 1 is C 16-36 alkylene.

[0028] [5] The silane compound according to any one of [1] to [4] above, wherein X 2 is a single bond, or a divalent group containing -CO-, -COO-, -OCO-, -NR 41 -, -CONR 41 -, -NR 41 CO-, -OCONR 41 -, -NR 41 -CO-NR 41 -, -O- or -S-.

[0029] R 41 is a hydrogen atom or C 1-6 alkyl.

[0030] [6] The silane compound according to any one of [1] to [5] above, wherein X 2 is a single bond or the following formula: -X 2A -X 2B -shown group.

[0031] [In the formula:

[0032] X 2A is -CO-, -COO-, -OCO-, -NR 41 ]-, -CONR 41 -, -NR 41 CO-, -OCONR 41 -, -NR 41 -CO-NR 41 -, -O- or -S-,

[0033] R 41 is a hydrogen atom or C 1-6 alkyl,

[0034] X 2B is a single bond or C 1-6 alkylene. ]

[0035] [7] The silane compound according to any one of [1] to [4] above, wherein X 2 is the group shown by the following formula.

[0036]

[0037] [In the formula, X a is a single bond or a divalent organic group. ]

[0038] [8] The silane compound according to any one of [1] to [7] above, wherein R Si is a group represented by the following formula (S1), (S2), (S3), (S4) or (S5).

[0039]

[0040] -SiR 11 n1 R 12 3-n1 (S2)

[0041] -SiR a1 k1 R b1 l1 R c1 m1 (S3)

[0042] -CR d1 k2 R e1 l2 R f1 m2 (S4)

[0043] -NR g1 R h1 (S5)

[0044] [In the formula:

[0045] R 11 are each independently a hydroxyl group or a hydrolyzable group,

[0046] R 12 are each independently a monovalent organic group,

[0047] n1 is each independently an integer of 0 to 3 in each (SiR 11 n1 R 12 3-n1 ) unit,

[0048] X 11 are each independently a single bond or a divalent organic group,

[0049] R 13 are each independently a hydrogen atom or a monovalent organic group,

[0050] t is each independently an integer of 2 or more,

[0051] R 14 are each independently a hydrogen atom, a halogen atom or -X 11 -SiR 11 n1R 12 3-n1 ,

[0052] R 15 are each independently a single bond, an oxygen atom, an alkylene group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms,

[0053] R a1 are each independently -Z 1 -SiR 21 p1 R 22 q1 R 23 r1 ;

[0054] Z 1 are each independently a divalent organic group,

[0055] R 21 are each independently -Z 1' -SiR 21' p1' R 22' q1' R 23' r1' ;

[0056] R 22 are each independently a hydroxyl group or a hydrolyzable group,

[0057] R 23 are each independently a monovalent organic group,

[0058] p1 are each independently an integer from 0 to 3,

[0059] q1 are each independently an integer from 0 to 3,

[0060] r1 are each independently an integer from 0 to 3,

[0061] Z 1' are each independently a divalent organic group,

[0062] R 21' are each independently -Z 1” -SiR 22” q1” R 23” r1” ;

[0063] R 22' are each independently a hydroxyl group or a hydrolyzable group,

[0064] R 23' are each independently a monovalent organic group,

[0065] p1' is independently an integer from 0 to 3,

[0066] q1' is independently an integer from 0 to 3,

[0067] r1' is independently an integer from 0 to 3,

[0068] Z 1” is independently a divalent organic group,

[0069] R 22” is independently a hydroxyl group or a hydrolyzable group,

[0070] R 23” is independently a monovalent organic group,

[0071] q1” is independently an integer from 0 to 3,

[0072] r1” is independently an integer from 0 to 3,

[0073] R b1 is independently a hydroxyl group or a hydrolyzable group,

[0074] R c1 is independently a monovalent organic group,

[0075] k1 is independently an integer from 0 to 3,

[0076] l1 is independently an integer from 0 to 3,

[0077] m1 is independently an integer from 0 to 3,

[0078] wherein, there are at least 2 Si atoms bonded with a hydroxyl group or a hydrolyzable group in formula (S3),

[0079] R d1 is independently -Z 2 -CR 31 p2 R 32 q2 R 33 r2 ,

[0080] Z 2 is independently a single bond, an oxygen atom or a divalent organic group,

[0081] R 31 is independently -Z 2' -CR 32' q2' R 33' r2' ,

[0082] R 32are each independently -Z 3 -SiR 34 n2 R 35 3-n2 ,

[0083] R 33 are each independently a hydrogen atom, a hydroxyl group or a monovalent organic group,

[0084] p2 are each independently an integer from 0 to 3,

[0085] q2 are each independently an integer from 0 to 3,

[0086] r2 are each independently an integer from 0 to 3,

[0087] Z 2' are each independently a single bond, an oxygen atom or a divalent organic group,

[0088] R 32' are each independently -Z 3 -SiR 34 n2 R 35 3-n2 ,

[0089] R 33' are each independently a hydrogen atom, a hydroxyl group or a monovalent organic group,

[0090] q2' are each independently an integer from 0 to 3,

[0091] r2' are each independently an integer from 0 to 3,

[0092] Z 3 are each independently a single bond, an oxygen atom or a divalent organic group;

[0093] R 34 are each independently a hydroxyl group or a hydrolyzable group,

[0094] R 35 are each independently a monovalent organic group,

[0095] n2 are each independently an integer from 0 to 3,

[0096] R e1 are each independently -Z 3 -SiR 34 n2 R 35 3-n2 ,

[0097] R f1 are each independently a hydrogen atom, a hydroxyl group or a monovalent organic group,

[0098] k2 is independently an integer from 0 to 3,

[0099] l2 is independently an integer from 0 to 3,

[0100] m2 is independently an integer from 0 to 3.

[0101] Among them, there are at least 2 Si atoms bonded with hydroxyl groups or hydrolyzable groups in formula (S4),

[0102] R g1 and R h1 are independently -Z 4 -SiR 11 n1 R 12 3-n1 、-Z 4 -SiR a1 k1 R b1 l1 R c1 m1 or -Z 4 -CR d1 k2 R e1 l2 R f1 m2 ,

[0103] Z 4 are independently a single bond, an oxygen atom or a divalent organic group,

[0104] Among them, there are at least 2 Si atoms bonded with hydroxyl groups or hydrolyzable groups in formula (S5).

[0105] [9] The silane compound according to any one of the above [1] to [8], wherein R 1 is R 2 -O-CO-, CH2=CH-, NH2- or a bromine atom,

[0106] R 2 is a methyl group,

[0107] X 1 is C 16-26 alkylene,

[0108] X 2 is a single bond, -CO- or -CONR 41 -,

[0109] R 41 is a hydrogen atom,

[0110] R Si is -SiR 113 (wherein R 11 is -OR h , R h is methyl), -CR e1 3 (wherein R e1 is -Z 3 -SiR 34 3, Z 3 is a C3 alkylene group, R 34 is -OR h , R h is methyl) or -NR g1 R h1 (wherein R g1 and R h1 are -Z 4 -SiR 11 3, Z 3 is a C3 alkylene group, R 11 is -OR h , R h is methyl) as represented by the group.

[0111]

[10] The compound according to any one of the above [1] to [9], which is selected from the following compounds:

[0112]

[0113]

[11] A surface treatment agent containing the silane compound according to any one of the above [1] to

[10] .

[0114]

[12] The surface treatment agent according to the above

[11] , further containing a condensate of the silane compound according to any one of the above [1] to

[10] .

[0115]

[13] The surface treatment agent according to the above [9] or

[12] , wherein the content of the silane compound and its condensate according to any one of the above [1] to

[10] is 60% by mass or more based on all the silane compounds contained in the surface treatment agent.

[0116]

[14] The surface treatment agent according to any one of the above

[11] to

[13] , further containing a compound selected from R 71 OR 72 , R 73 n8 C6H 6-n8 , R 74 R 75 R 76 Si-(O-SiR 77 R 78 ) m8 -R 79 , (OSiR 77 R 78 )m9 The compound shown, and a C that may be substituted 1-10 solvent in an alcohol.

[0117] [In the formula:

[0118] R 71 ~R 79 are each independently a monovalent organic group having 1 to 10 carbon atoms,

[0119] m8 is an integer from 1 to 6,

[0120] m9 is an integer from 4 to 8,

[0121] n8 is an integer from 0 to 6.]

[0122]

[15] The surface treatment agent according to any one of

[11] to

[14] above, which is used for vacuum evaporation coating.

[0123]

[16] The surface treatment agent according to any one of

[11] to

[14] above, which is used for wet covering.

[0124]

[17] A pellet containing the surface treatment agent according to any one of

[11] to

[16] above.

[0125]

[18] An article, which includes a substrate and a layer formed on the substrate from the silane compound according to any one of [1] to

[10] above or the surface treatment agent according to any one of

[11] to

[16] above.

[0126]

[19] The article according to

[18] above, wherein an intermediate layer containing silicon oxide is included between the substrate and the layer.

[0127]

[20] The article according to

[19] above, wherein the intermediate layer contains an alkali metal atom.

[0128]

[21] The article according to

[20] above, wherein at least a part of the alkali metal atom is a sodium atom.

[0129]

[22] The article according to any one of

[18] to

[21] above, which is an optical component.

[0130]

[23] The article according to any one of

[18] to

[22] above, which is a display.

[0131]

[24] A compound represented by the following formula (2).

[0132] R 1 -X 1 -R 51 (2)

[0133] [In the formula:

[0134] R 1 is R 2 -O-CO-, R 2 -O-C(=O)-O-, R 2 -NR-CO-, R 2 -CO-NR-, R 2 -OCO-NR-, R 2 -NR 3 -COO-, R 2 -NR-CO-NR 3 -, CH2=CH-, NHR 3 -, or a halogen atom,

[0135] R 2 is a hydrogen atom, C 1-6 alkyl, or a group of oxyalkylene having 1 to 30 carbon atoms,

[0136] R 3 is a hydrogen atom or C 1-6 alkyl,

[0137] X 1 is an alkylene having 12 or more carbon atoms,

[0138] R 51 is the following group:

[0139]

[0140] R 61 is a hydrocarbon group having 1 to 6 carbon atoms,

[0141] * indicates the bonding site.]

[0142] Advantages of the Invention

[0143] According to the present invention, there is provided a compound capable of forming a surface treatment layer having low visibility of attached fingerprints and high friction durability. Detailed Embodiments

[0144] As used in this specification, a "monovalent organic group" refers to a monovalent group containing carbon. The monovalent organic group is not particularly limited and may be a hydrocarbon group or a derivative thereof. A derivative of a hydrocarbon group refers to a group having one or more N, O, S, Si, amide group, sulfonyl group, siloxane, carbonyl group, carbonyloxy group, etc. at the terminal or in the molecular chain of the hydrocarbon group. Among them, when only "organic group" is mentioned, it means a monovalent organic group. In addition, a "divalent organic group" refers to a divalent group containing carbon. Examples of such divalent organic groups include divalent groups obtained by further removing one hydrogen atom from an organic group. The same applies to trivalent or higher-valent organic groups, which mean groups obtained by removing a specified number of hydrogen atoms from an organic group.

[0145] As used in this specification, a "hydrocarbon group" is a group containing carbon and hydrogen, and refers to a group obtained by removing a hydrogen atom from a hydrocarbon. The hydrocarbon group is not particularly limited, and examples thereof include C1- 20 hydrocarbon groups, such as aliphatic hydrocarbon groups, aromatic hydrocarbon groups, etc. The above-mentioned "aliphatic hydrocarbon group" can be any of linear, branched or cyclic, and can also be any of saturated or unsaturated. In addition, the hydrocarbon group may contain one or more ring structures. The hydrocarbon group may also be substituted with one or more substituents.

[0146] As used in this specification, the substituents of a "hydrocarbon group" are not particularly limited. For example, they may be selected from halogen atoms, C 1-6 alkyl groups that can be substituted with one or more halogen atoms, C 2-6 alkenyl groups, C 2-6 alkynyl groups, C 3-10 cycloalkyl groups, C 3-10 unsaturated cycloalkyl groups, 5- to 10-membered heterocyclic groups, 5- to 10-membered unsaturated heterocyclic groups, C 6﹣10 aryl groups, and 5- to 10-membered heteroaryl groups, and one or more groups thereof.

[0147] As used in this specification, a "hydrolyzable group" refers to a group that can undergo a hydrolysis reaction, that is, a group that can be detached from the main skeleton of a compound through a hydrolysis reaction. Examples of hydrolyzable groups include -OR h , -OCOR h , -O-N=CR h 2, -NR h 2, -NHR h , -NCO or halogen (in these formulas, R h represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms), etc., and preferably -OR h (i.e., an alkoxy group). R hExamples include: unsubstituted alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl; substituted alkyl groups such as chloromethyl. Among these, alkyl groups are preferred, unsubstituted alkyl groups are particularly preferred, and methyl or ethyl are more preferred.

[0148] (Silane compound)

[0149] The present invention provides a silane compound represented by the following formula (1).

[0150] (R 1 -X 1 ) α -X 2 -(R Si ) β (1)

[0151] [In the formula:

[0152] R 1 is R 2 -O-CO-, R 2 -CO-O-, R 2 -O-C(=O)-O-, R 2 -NR-CO-, R 2 -CO-NR-, R 2 -OCO-NR-, R 2 -NR 3 -COO-, R 2 -NR-CO-NR 3 -, CH2=CH-, NHR 3 -, CR 5 3-, CHR 5 2-, CH2R 5 -, or a halogen atom,

[0153] R 2 is a hydrogen atom, C 1-6 alkyl or a group of oxyalkylene having 1 to 30 carbon atoms,

[0154] R 3 is a hydrogen atom or C 1-6 alkyl,

[0155] R 5 is a halogen atom,

[0156] X 1 is an alkylene group having 12 or more carbon atoms,

[0157] X 2 is a single bond or a 2- to 10-valent organic group,

[0158] R Si is a monovalent group containing a Si atom bonded with a hydroxyl group or a hydrolyzable group,

[0159] α is an integer from 1 to 9,

[0160] β is an integer from 1 to 9,

[0161] The sum of α and β is equal to X 2 valence number.]

[0162] The compound of the present invention has a polar functional group such as an ester group near the end on the air interface side (R 1 side), or a vinyl group, an amino group or a halogen group. Therefore, the surface treatment layer obtained from this compound has improved affinity for fingerprints, and as a result, it can be considered that the visibility of the attached fingerprints becomes lower. Especially when there is an alkyl group at the end, the smaller the better; when there is an oxyalkylene group, there is no particular relationship with the chain length, and the affinity for fingerprints is improved.

[0163] In the above formula, R 1 is R 2 -O-CO-, R 2 -CO-O-, R 2 -O-C(=O)-O-, R 2 -NR-CO-, R 2 -CO-NR-, R 2 -OCO-NR-, R 2 -NR 3 -COO-, R 2 -NR-CO-NR 3 -, CH2=CH-, NHR 3 -, CR 5 3-, CHR 5 2-, CH2R 5 - or a halogen atom.

[0164] R 2 is a hydrogen atom, a C 1-6 alkyl group or a group containing an oxyalkylene group with 1 to 30 carbon atoms, preferably a hydrogen atom or a C 1-6 alkyl group, more preferably a C 1-6 alkyl group.

[0165] The above C 1-6 alkyl group can be straight-chain or branched-chain. The C 1-6 alkyl group is preferably a C 1-4 alkyl group, more preferably a methyl group or an ethyl group, and further preferably a methyl group.

[0166] The above group containing an oxyalkylene group with 1 to 30 carbon atoms is a group containing -O-C 1-30 alkylene-, for example, is -R 81 -( -O-C 1-30 alkylene) n-R 82 (wherein R 81 is a single bond or a divalent organic group, preferably a C 1-6 alkylene group, n is an arbitrary integer, preferably an integer from 1 to 10, and R 82 is a hydrogen atom or a monovalent organic group, preferably a C 1-6 alkyl group, more preferably a methyl group). The above-mentioned alkylene group can be linear or branched.

[0167] R 3 is a hydrogen atom or a C 1-6 alkyl group, preferably a hydrogen atom.

[0168] The above-mentioned C 1-6 alkyl group can be linear or branched. The C 1-6 alkyl group is preferably a C 1-4 alkyl group, more preferably a methyl or ethyl group, and further preferably a methyl group.

[0169] The above-mentioned halogen atom is chlorine, bromine or iodine, preferably bromine.

[0170] R 1 is preferably R 2 -O-CO-, CH2=CH-, NH2- or a bromine atom, and R 2 is a C 1-6 alkyl group, preferably a C 1-4 alkyl group, more preferably a methyl group.

[0171] In one embodiment, R 1 is R 2 -O-CO- or CH2=CH-, and R 2 is a C 1-6 alkyl group, preferably a C 1-4 alkyl group, more preferably a methyl group.

[0172] In the above formula, X 1 is an alkylene group having 12 or more carbon atoms, preferably an alkylene group having 16 or more carbon atoms, and further preferably an alkylene group having 20 or more carbon atoms.

[0173] X 1 There is no particular limitation on the upper limit of the number of carbon atoms of X, preferably 32, more preferably 28, and for example, it can be 26 or 23.

[0174] X 1 is preferably a C 12-36 alkylene group, more preferably a C 16-36 alkylene group, and further preferably a C 20-32 alkylene group.

[0175] In the above formula, X 2 is a single bond or a divalent to 10-valent organic group.

[0176] In one embodiment, X 2 is a single bond.

[0177] In another embodiment, X 2 is an organic group with a valence of 2 to 10.

[0178] In a preferred embodiment, X 2 is a divalent organic group. When X 2 is a divalent organic group, α and β in the formula are 1.

[0179] The above divalent organic group is preferably a divalent group containing -CO-, -COO-, -OCO-, -NR 41 -, -CONR 41 -, -NR 41 CO-, -OCONR 41 -, -NR 41 -CO-NR 41 -, -O- or -S-, where R 41 is a hydrogen atom or a C 1-6 alkyl group.

[0180] The C 41 in R 1-6 alkyl group can be straight-chain or branched-chain. In one embodiment, the above C 1-6 alkyl group is straight-chain. In another embodiment, the above C 1-6 alkyl group is branched-chain. The above C 1-6 alkyl group is preferably a C 1-4 alkyl group, more preferably a C 1-3 alkyl group, further preferably methyl or ethyl, and particularly preferably methyl.

[0181] In one embodiment, R 41 is a hydrogen atom.

[0182] The above divalent group is preferably a group represented by the following formula: -X 2A -X 2B -.

[0183] [In the formula:

[0184] X 2A is -CO-, -COO-, -OCO-, -NR 41 -, -CONR 41 -, -NR 41 CO-, -OCONR 41 -, -NR 41 -CO-NR 41 -, -O- or -S-, and R 41 is a hydrogen atom or a C 1-6 alkyl group,

[0185] X 2B is a single bond or C 1-6 alkylene.]

[0186] X 2A is preferably -CO-, -CONR 41 -, or -OCONR 41 -. R 41 is preferably a hydrogen atom.

[0187] In one embodiment, X 2B is a single bond.

[0188] In another embodiment, X 2B is C 1-6 alkylene.

[0189] X 2B The C 1-6 alkylene in can be straight-chain or branched-chain. In one embodiment, the above C 1-6 alkylene is straight-chain. In another embodiment, the above C 1-6 alkylene is branched-chain. The above C 1-6 alkylene is preferably C 1-4 alkylene, more preferably C 1-3 alkylene.

[0190] -X 2A -X 2B - is preferably -CO-, -CONR 41 -X 2B -. R 41 is preferably a hydrogen atom. X 2B is preferably C 1-6 alkylene.

[0191] In a preferred embodiment, X 2 is a trivalent organic group.

[0192] When X 2 is a trivalent organic group, α is 2 and β is 1, or α is 1 and β is 2.

[0193] The above trivalent organic group preferably includes the groups represented by the following formula:

[0194]

[0195] [In the formula, X a is a single bond or a divalent organic group.]

[0196] X a is a single bond or a divalent linking group directly bonded to the isocyanurate ring. As X a, preferably a single bond, an alkylene group, or a divalent group containing at least one bond selected from an ether bond, an ester bond, an amide bond, and a thioether bond, more preferably a single bond, an alkylene group having 1 to 10 carbon atoms, or a divalent hydrocarbon group having 1 to 10 carbon atoms and containing at least one bond selected from an ether bond, an ester bond, an amide bond, and a thioether bond.

[0197] As X a , more preferably the following formula: -(CX 121 X 122 ) x1 -(X a1 ) y1 -(CX 123 X 124 ) z1 -represented group.

[0198] (In the formula, X 121 ~X 124 are each independently H, F, OH or -OSi(OR 121 )3 (wherein the three Rs 121 are each independently an alkyl group having 1 to 4 carbon atoms),

[0199] The above X a1 is -C(=O)NH-, -NHC(=O)-, -O-, -C(=O)O-, -OC(=O)-, -OC(=O)O- or -NHC(=O)NH- (the left side of each bond is bonded to CX 121 X 122 ),

[0200] x1 is an integer from 0 to 10, y1 is 0 or 1, and z1 is an integer from 1 to 10.)

[0201] As the above X a1 , preferably -O- or -C(=O)O-.

[0202] As the above X a , particularly preferably the following formula:

[0203] -(CH2) m12 -O-(CH2) m13 -(wherein, m12 is an integer from 1 to 3, and m13 is an integer from 1 to 3) represented group,

[0204] -(CH2) m15 -O-CH2CH(OH)-(CH2) m16 -(wherein, m15 is an integer from 1 to 3, and m16 is an integer from 1 to 3) represented group,

[0205] -(CH2) m18- (wherein, m18 is an integer from 1 to 3), and

[0206] - (CH2) m20 - O - CH2CH(OSi(OCH3)3) - (CH2) m21 - (wherein, m20 is an integer from 1 to 3, and m21 is an integer from 1 to 3).

[0207] As the above X a , there is no particular limitation, and specifically, examples include: - CH2 -, - C2H4 -, - C3H6 -, - C4H8 -, - C4H8 - O - CH2 -, - CO - O - CH2 - CH(OH) - CH2 -, - S -, - NR 121 -, - (CH2) m22 - C(=O) - O - (CH2) m23 -, - (CH2) m22 - O - C(=O) - (CH2) m23 -, - (CH2) m22 - C(=O) - NR 121 - (CH2) m23 -, - (CH2) m22 - NR 121 - C(=O) - (CH2) m23 - CH2OCH2CH(OSi(OCH3)3)CH2 - (where R 121 is a C 1-6 hydrocarbon chain, m22 is an integer from 1 to 10, and m23 is an integer from 1 to 10), etc.

[0208] In a preferred embodiment, R Si is a group represented by the following formula (S1), (S2), (S3), (S4), or (S5).

[0209]

[0210] - SiR 11 n1 R 12 3-n1 (S2)

[0211] - SiR a1 k1 R b1 l1 R c1 m1 (S3)

[0212] - CR d1 k2 R e1 l2 Rf1 m2 (S4)

[0213] -NR g1 R h1 (S5)

[0214] [wherein:

[0215] R 11 are each independently a hydroxyl group or a hydrolyzable group,

[0216] R 12 are each independently a monovalent organic group,

[0217] n1 is each independently an integer of 0 to 3 in each (SiR 11 n1 R 12 3-n1 ) unit,

[0218] X 11 are each independently a single bond or a divalent organic group,

[0219] R 13 are each independently a hydrogen atom or a monovalent organic group,

[0220] t is each independently an integer of 2 or more,

[0221] R 14 are each independently a hydrogen atom, a halogen atom or -X 11 -SiR 11 n1 R 12 3-n1 ,

[0222] R 15 are each independently a single bond, an oxygen atom, an alkylene group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms,

[0223] R a1 are each independently -Z 1 -SiR 21 p1 R 22 q1 R 23 r1 ;

[0224] Z 1 are each independently a divalent organic group,

[0225] R 21 are each independently -Z 1' -SiR 21' p1' R 22'q1' R 23' r1' ;

[0226] R 22 are each independently a hydroxyl group or a hydrolyzable group,

[0227] R 23 are each independently a monovalent organic group,

[0228] p1 are each independently an integer from 0 to 3,

[0229] q1 are each independently an integer from 0 to 3,

[0230] r1 are each independently an integer from 0 to 3,

[0231] Z 1' are each independently a divalent organic group,

[0232] R 21' are each independently -Z 1” -SiR 22” q1” R 23” r1” ;

[0233] R 22' are each independently a hydroxyl group or a hydrolyzable group,

[0234] R 23' are each independently a monovalent organic group,

[0235] p1' are each independently an integer from 0 to 3,

[0236] q1' are each independently an integer from 0 to 3,

[0237] r1' are each independently an integer from 0 to 3,

[0238] Z 1” are each independently a divalent organic group,

[0239] R 22” are each independently a hydroxyl group or a hydrolyzable group,

[0240] R 23” are each independently a monovalent organic group,

[0241] q1” are each independently an integer from 0 to 3,

[0242] r1” are each independently an integer from 0 to 3,

[0243] R b1 are each independently a hydroxyl group or a hydrolyzable group,

[0244] R c1 are each independently monovalent organic groups,

[0245] k1 are each independently integers from 0 to 3,

[0246] l1 are each independently integers from 0 to 3,

[0247] m1 are each independently integers from 0 to 3,

[0248] wherein, there are at least 2 Si atoms bonded with hydroxyl groups or hydrolyzable groups in formula (S3),

[0249] R d1 are each independently -Z 2 -CR 31 p2 R 32 q2 R 33 r2 ,

[0250] Z 2 are each independently a single bond, an oxygen atom or a divalent organic group,

[0251] R 31 are each independently -Z 2' -CR 32' q2' R 33' r2' ,

[0252] R 32 are each independently -Z 3 -SiR 34 n2 R 35 3-n2 ,

[0253] R 33 are each independently a hydrogen atom, a hydroxyl group or a monovalent organic group,

[0254] p2 are each independently integers from 0 to 3,

[0255] q2 are each independently integers from 0 to 3,

[0256] r2 are each independently integers from 0 to 3,

[0257] Z 2' are each independently a single bond, an oxygen atom or a divalent organic group,

[0258] R 32' are each independently -Z 3 -SiR 34 n2 R35 3-n2 ,

[0259] R 33' are each independently a hydrogen atom, a hydroxyl group or a monovalent organic group,

[0260] q2' are each independently an integer from 0 to 3,

[0261] r2' are each independently an integer from 0 to 3,

[0262] Z 3 are each independently a single bond, an oxygen atom or a divalent organic group;

[0263] R 34 are each independently a hydroxyl group or a hydrolyzable group,

[0264] R 35 are each independently a monovalent organic group,

[0265] n2 are each independently an integer from 0 to 3,

[0266] R e1 are each independently -Z 3 -SiR 34 n2 R 35 3-n2 ,

[0267] R f1 are each independently a hydrogen atom, a hydroxyl group or a monovalent organic group,

[0268] k2 are each independently an integer from 0 to 3,

[0269] l2 are each independently an integer from 0 to 3,

[0270] m2 are each independently an integer from 0 to 3.

[0271] Among them, there are at least 2 Si atoms bonded with a hydroxyl group or a hydrolyzable group in formula (S4),

[0272] R g1 and R h1 are each independently -Z 4 -SiR 11 n1 R 12 3-n1 , -Z 4 -SiR a1 k1 R b1 l1 R c1 m1 or -Z 4 -CRd1 k2 R e1 l2 R f1 m2 ,

[0273] Z 4 are each independently a single bond, an oxygen atom or a divalent organic group,

[0274] wherein there are at least 2 Si atoms bonded to a hydroxyl group or a hydrolyzable group in formula (S5).]

[0275] In the above formula, R 11 are each independently a hydroxyl group or a hydrolyzable group.

[0276] R 11 are preferably each independently a hydrolyzable group.

[0277] R 11 are preferably each independently —OR h , —OCOR h , —O—N═CR h 2, —NR h 2, —NHR h , —NCO or a halogen (in these formulas, R h represents a substituted or unsubstituted C 1-4 alkyl), more preferably —OR h (i.e., an alkoxy group). As R h , examples include: unsubstituted alkyls such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl; substituted alkyls such as chloromethyl. Among these, alkyls are preferred, especially unsubstituted alkyls, and more preferably methyl or ethyl. In one embodiment, R h is methyl, and in another embodiment, R h is ethyl.

[0278] In the above formula, R 12 are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups other than the above hydrolyzable groups.

[0279] In R 12 , the monovalent organic group is preferably a C 1-20 alkyl, more preferably a C 1-6 alkyl, and even more preferably methyl.

[0280] In the above formula, n1 is each independently an integer of 0 to 3 in each (SiR 11 n1 R 12 3-n1 ) unit. Among them, in formula (S1), n1 is 1 to 3 for (SiR11 n1 R 12 3-n1 ) units are at least 2. In other words, there are at least 2 Si atoms bonded to a hydroxyl group or a hydrolyzable group in formula (S1).

[0281] n1 is independently preferably an integer of 1 to 3, more preferably 2 to 3, and still more preferably 3 in each (SiR 11 n1 R 12 3-n1 ) unit.

[0282] In the above formula, X 11 is independently a single bond or a divalent organic group. Such a divalent organic group is preferably -R 28 -O x -R 29 -(wherein R 28 and R 29 are independently a single bond or a C 1-20 alkylene group, and x is 0 or 1). Such a C 1-20 alkylene group can be linear or branched, preferably linear. Such a C 1-20 alkylene group is preferably a C 1-10 alkylene group, more preferably a C 1-6 alkylene group, still more preferably a C 1-3 alkylene group.

[0283] In one embodiment, X 11 is independently -C 1-6 alkylene-O-C 1-6 alkylene- or -O-C 1-6 alkylene-.

[0284] In a preferred embodiment, X 11 is independently a single bond or a linear C 1-6 alkylene group, preferably a single bond or a linear C 1-3 alkylene group, more preferably a single bond or a linear C 1-2 alkylene group, still more preferably a linear C 1-2 alkylene group.

[0285] In the above formula, R 13 is independently a hydrogen atom or a monovalent organic group. Such a monovalent organic group is preferably a C 1-20 alkyl group.

[0286] In a preferred embodiment, R 13 is independently a hydrogen atom or a linear C 1-6 alkyl group, preferably a hydrogen atom or a linear C 1-3An alkyl group, more preferably a hydrogen atom or a methyl group.

[0287] In the above formula, R 15 Are each independently a single bond, an oxygen atom, an alkylene group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms.

[0288] In one embodiment, R 15 Are each independently an oxygen atom, an alkylene group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms.

[0289] In a preferred embodiment, R 15 Is a single bond.

[0290] In the above formula, t are each independently an integer of 2 or more.

[0291] In a preferred embodiment, t are each independently an integer from 2 to 10, preferably an integer from 2 to 6.

[0292] In the above formula, R 14 Are each independently a hydrogen atom, a halogen atom or -X 11 -SiR 11 n1 R 12 3- n1 . Such a halogen atom is preferably an iodine atom, a chlorine atom or a fluorine atom, more preferably a fluorine atom. In a preferred embodiment, R 14 Is a hydrogen atom.

[0293] In one embodiment, formula (S1) is the following formula (S1-a).

[0294]

[0295] [Wherein,

[0296] R 11 , R 12 , R 13 , X 11 And the meanings of n1 are the same as those described in the above formula (S1),

[0297] t1 and t2 are each independently an integer of 1 or more, preferably an integer from 1 to 10, more preferably an integer from 2 to 10, for example an integer from 1 to 5 or an integer from 2 to 5,

[0298] The order of existence of each repeating unit marked with t1 and t2 and enclosed in parentheses is arbitrary in the formula.]

[0299] In a preferred embodiment, formula (S1) is the following formula (S1-b).

[0300]

[0301] [In the formula, R 11 , R 12 , R 13 , X 11 , n1 and t have the same meanings as described in the above formula (S1).]

[0302] In a preferred embodiment, in formula (S2), the Si atom of -SiR 11 n1 R 12 3-n1 does not form a siloxane bond.

[0303] R a1 are each independently -Z 1 -SiR 21 p1 R 22 q1 R 23 r1 .

[0304] Z 1 are each independently an oxygen atom or a divalent organic group. Among them, the right side of the structure denoted as Z 1 is bonded to the (SiR 21 p1 R 22 q1 R 23 r1 ) bond.

[0305] In a preferred embodiment, Z 1 is a divalent organic group.

[0306] In a preferred embodiment, the case where Z 1 forms a siloxane bond with the Si atom to which Z 1 is bonded is not included. Preferably, in formula (S3), (Si-Z 1 -Si) does not contain a siloxane bond.

[0307] Z 1 is preferably C 1-6 alkylene, -(CH2) z1 -O-(CH2) z2 -(wherein, z1 is an integer from 0 to 6, such as an integer from 1 to 6, z2 is an integer from 0 to 6, such as an integer from 1 to 6) or -(CH2) z3 -arylene-(CH2) z4 -(wherein, z3 is an integer from 0 to 6, such as an integer from 1 to 6, z4 is an integer from 0 to 6, such as an integer from 1 to 6). Such C 1-6 alkylene can be straight-chain or branched-chain, preferably straight-chain. These groups can be selected from, for example, a fluorine atom, C1-6 Alkyl, C 2-6 alkenyl, and C 2-6 is substituted with one or more substituents selected from alkynyl, but is preferably unsubstituted.

[0308] In a preferred embodiment, Z 1 is C 1-6 alkylene or -(CH2) z3 -phenylene-(CH2) z4 -, preferably -phenylene-(CH2) z4 -.

[0309] In another preferred embodiment, Z 1 is C 1-3 alkylene. In one embodiment, Z 1 may be -CH2CH2CH2-. In another embodiment, Z 1 may be -CH2CH2-.

[0310] R 21 are each independently -Z 1' -SiR 21' p1' R 22' q1' R 23' r1' .

[0311] Z 1' are each independently an oxygen atom or a divalent organic group. Among them, the right side of the structure denoted as Z 1' is bonded to (SiR 21' p1' R 22' q1' R 23' r1' ).

[0312] In a preferred embodiment, Z 1' is a divalent organic group.

[0313] In a preferred embodiment, it does not include the case where Z 1' and the Si atom to which Z 1' is bonded form a siloxane bond. Preferably, (Si-Z 1' -Si) in formula (S3) does not contain a siloxane bond.

[0314] Z 1' is preferably C 1-6 alkylene, -(CH2) z1' -O-(CH2) z2' -(wherein, z1' is an integer from 0 to 6, for example, an integer from 1 to 6, z2' is an integer from 0 to 6, for example, an integer from 1 to 6) or -(CH2)z3' -phenylene-(CH2) z4' -(wherein, z3' is an integer from 0 to 6, such as an integer from 1 to 6, and z4' is an integer from 0 to 6, such as an integer from 1 to 6). Such a C 1-6 alkylene group can be linear or branched, preferably linear. These groups can be substituted with one or more substituents selected from, for example, a fluorine atom, C 1-6 alkyl, C 2-6 alkenyl, and C2-6 alkynyl, but are preferably unsubstituted.

[0315] In a preferred embodiment, Z 1' is C 1-6 alkylene or -(CH2) z3' -phenylene-(CH2) z4' -, preferably -phenylene-(CH2) z4' -.

[0316] In another preferred embodiment, Z 1' is C 1-3 alkylene. In one embodiment, Z 1' can be -CH2CH2CH2-. In another embodiment, Z 1' can be -CH2CH2-.

[0317] Each of the above R 21' is independently -Z 1” -SiR 22” q1” R 23” r1” .

[0318] Each of the above Z 1” is independently an oxygen atom or a divalent organic group. Among them, the right side of the structure denoted as Z 1” is bonded to (SiR 22” q1” R 23” r1” ).

[0319] In a preferred embodiment, Z 1” is a divalent organic group.

[0320] In a preferred embodiment, the case where Z 1” forms a siloxane bond with the Si atom to which Z 1” is bonded is not included. Preferably, (Si-Z 1” -Si) in formula (S3) does not contain a siloxane bond.

[0321] Z 1” is preferably C 1-6 alkylene, -(CH2) z1”-O-(CH2) z2” -(wherein, z1" is an integer from 0 to 6, such as an integer from 1 to 6, and z2" is an integer from 0 to 6, such as an integer from 1 to 6) or -(CH2) z3” -phenylene-(CH2) z4” -(wherein, z3" is an integer from 0 to 6, such as an integer from 1 to 6, and z4" is an integer from 0 to 6, such as an integer from 1 to 6). Such a C 1-6 alkylene group can be straight-chain or branched-chain, preferably straight-chain. These groups can be substituted with one or more substituents selected from, for example, a fluorine atom, C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl, but are preferably unsubstituted.

[0322] In a preferred embodiment, Z 1” is C 1-6 alkylene or -(CH2) z3” -phenylene-(CH2) z4” -, preferably -phenylene-(CH2) z4” -. When Z 1” is such a group, the light resistance, especially the ultraviolet resistance, can be further improved.

[0323] In another preferred embodiment, Z 1” is C 1-3 alkylene. In one embodiment, Z 1” can be -CH2CH2CH2-. In another embodiment, Z 1” can be -CH2CH2-.

[0324] Each of the above R 22” is independently a hydroxyl group or a hydrolyzable group.

[0325] Each of the above R 22” is preferably independently a hydrolyzable group.

[0326] Each of the above R 22” is preferably independently -OR h , -OCOR h , -O-N=CR h 2, -NR h 2, -NHR h or -NCO (in these formulas, R h represents a substituted or unsubstituted C 1-4 alkyl), more preferably -OR h (i.e., an alkoxy group). As R h, examples include: non-substituted alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, and isobutyl; and substituted alkyl groups such as chloromethyl. Among these, alkyl groups, especially non-substituted alkyl groups, are preferred, and methyl or ethyl is more preferred. In one embodiment, R h is methyl, and in another embodiment, R h is ethyl.

[0327] R 23” are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups other than the above hydrolyzable groups.

[0328] In R 23” , the monovalent organic group is preferably a C 1-20 alkyl group, more preferably a C 1-6 alkyl group, and even more preferably methyl.

[0329] q1” are each independently an integer from 0 to 3, and the above r1” are each independently an integer from 0 to 3. Among them, the sum of q1” and r1” is 3 in the (SiR 22” q1” R 23” r1” ) unit.

[0330] q1” is preferably an integer from 1 to 3, more preferably 2 to 3, and even more preferably 3, respectively independently in each (SiR 22” q1” R 23” r1” ) unit.

[0331] R 22' are each independently a hydroxyl group or a hydrolyzable group.

[0332] R 22' is preferably each independently a hydrolyzable group.

[0333] R 22' is preferably each independently -OR h , -OCOR h , -O-N=CR h 2, -NR h 2, -NHR h or -NCO (in these formulas, R h represents a substituted or unsubstituted C 1-4 alkyl group), and more preferably -OR h (i.e., an alkoxy group). As R h , examples include: non-substituted alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, and isobutyl; and substituted alkyl groups such as chloromethyl. Among these, alkyl groups, especially non-substituted alkyl groups, are preferred, and methyl or ethyl is more preferred. In one embodiment, Rh is methyl, and in another embodiment, R h is ethyl.

[0334] R 23' are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups other than the above hydrolyzable groups.

[0335] In R 23' , the monovalent organic group is preferably a C 1-20 alkyl group, more preferably a C 1-6 alkyl group, and even more preferably methyl.

[0336] p1' are each independently an integer from 0 to 3, q1' are each independently an integer from 0 to 3, and r1' are each independently 0 to 3. Among them, the sum of p', q1' and r1' is 3 in the (SiR 21' p1' R 22' q1' R 23' r1' ) unit.

[0337] In one embodiment, p1' is 0.

[0338] In one embodiment, p1' can be each independently an integer from 1 to 3, an integer from 2 to 3, or 3 in each (SiR 21' p1' R 22' q1' R 23' r1' ) unit. In a preferred embodiment, p1' is 3.

[0339] In one embodiment, q1' is each independently an integer from 1 to 3, preferably an integer from 2 to 3, and more preferably 3 in each (SiR 21' p1' R 22' q1' R 23' r1' ) unit.

[0340] In one embodiment, p1' is 0, and q1' is each independently an integer from 1 to 3, preferably an integer from 2 to 3, and even more preferably 3 in each (SiR 21' p1' R 22' q1' R 23' r1' ) unit.

[0341] R 22 are each independently a hydroxyl group or a hydrolyzable group.

[0342] R 22 Preferably, they are each independently a hydrolyzable group.

[0343] R 22 Preferably, they are each independently -OR h , -OCOR h , -O-N=CR h 2, -NR h 2, -NHR h or -NCO (in these formulas, R h represents a substituted or unsubstituted C 1-4 alkyl), more preferably -OR h (i.e., an alkoxy group). As R h , examples include: unsubstituted alkyls such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl; and substituted alkyls such as chloromethyl. Among these, an alkyl, especially an unsubstituted alkyl, is preferred, and methyl or ethyl is more preferred. In one embodiment, R h is methyl, and in another embodiment, R h is ethyl.

[0344] The above R 23 are each independently a monovalent organic group. Such a monovalent organic group is a monovalent organic group other than the above hydrolyzable groups.

[0345] In R 23 , the monovalent organic group is preferably a C 1-20 alkyl, more preferably a C 1-6 alkyl, and even more preferably methyl.

[0346] The above p1 are each independently an integer from 0 to 3, q1 are each independently an integer from 0 to 3, and r1 are each independently an integer from 0 to 3. Among them, the sum of p1, q1, and r1 is 3 in the (SiR 21 p1 R 22 q1 R 23 r1 ) unit.

[0347] In one embodiment, p1 is 0.

[0348] In one embodiment, p1 can be each independently an integer from 1 to 3, an integer from 2 to 3, or 3 in each (SiR 21 p1 R 22 q1 R 23 r1 ) unit. In a preferred embodiment, p1 is 3.

[0349] In one mode, q1 is an integer from 1 to 3, preferably an integer from 2 to 3, more preferably 3, independently for each (SiR 21 p1 R 22 q1 R 23 r1 ) unit.

[0350] In one mode, p1 is 0, and q1 is an integer from 1 to 3, preferably an integer from 2 to 3, further preferably 3, independently for each (SiR 21 p1 R 22 q1 R 23 r1 ) unit.

[0351] In the formula, R b1 is independently a hydroxyl group or a hydrolyzable group.

[0352] R b1 is preferably independently a hydrolyzable group.

[0353] R b1 is preferably independently -OR h , -OCOR h , -O-N=CR h 2, -NR h 2, -NHR h or -NCO (in these formulas, R h represents a substituted or unsubstituted C 1-4 alkyl), more preferably -OR h (i.e., an alkoxy group). As R h , examples include: unsubstituted alkyls such as methyl, ethyl, n-propyl, isopropyl, n-butyl, and isobutyl; substituted alkyls such as chloromethyl. Among these, an alkyl, particularly an unsubstituted alkyl, is preferred, and methyl or ethyl is more preferred. In one mode, R h is methyl, and in another mode, R h is ethyl.

[0354] In the formula, R c1 is independently a monovalent organic group. Such a monovalent organic group is a monovalent organic group other than the above-mentioned hydrolyzable groups.

[0355] In R c1 , the monovalent organic group is preferably a C 1-20 alkyl, more preferably a C 1-6 alkyl, and further preferably methyl.

[0356] k1 is independently an integer from 0 to 3, l1 is independently an integer from 0 to 3, and m1 is independently an integer from 0 to 3. Among them, the sum of k1, l1, and m1 is 3 in the (SiR a1 k1 R b1 l1 R c1 m1 ) unit.

[0357] In one mode, k1 is independently an integer from 1 to 3, preferably 2 or 3, more preferably 3 in each (SiR a1 k1 R b1 l1 R c1 m1 ) unit. In a preferred mode, k1 is 3.

[0358] There are at least 2 Si atoms bonded with a hydroxyl group or a hydrolyzable group in formula (S3).

[0359] In a preferred mode, at the terminal part of formula (S3), there are at least 2 Si atoms bonded with a hydroxyl group or a hydrolyzable group.

[0360] In a preferred mode, the group represented by formula (S3) has -Z 1 -SiR 22 q1 R 23 r1 (wherein, q1 is an integer from 1 to 3, preferably 2 or 3, more preferably 3, and r1 is an integer from 0 to 2), -Z 1' -SiR 22' q1' R 23' r1' (wherein, q1' is an integer from 1 to 3, preferably 2 or 3, more preferably 3, and r1' is an integer from 0 to 2) or -Z 1” -SiR 22” q1” R 23” r1” (wherein, q1” is an integer from 1 to 3, preferably 2 or 3, more preferably 3, and r1” is an integer from 0 to 2). The meanings of Z 1 , Z 1' , Z 1” , R 22 , R 23 , R 22' , R 23' , R 22” and R 23” are the same as above.

[0361] In a preferred embodiment, when R is present in formula (S3) 21' at least one, preferably all, of the R 21' q1” in is an integer from 1 to 3, preferably 2 or 3, more preferably 3.

[0362] In a preferred embodiment, when R is present in formula (S3) 21 at least one, preferably all, of the R 21 p1' is 0 and q1' is an integer from 1 to 3, preferably 2 or 3, more preferably 3.

[0363] In a preferred embodiment, when R is present in formula (S3) a1 at least one, preferably all, of the R a1 p1 is 0 and q1 is an integer from 1 to 3, preferably 2 or 3, more preferably 3.

[0364] In a preferred embodiment, in formula (S3), k1 is 2 or 3, preferably 3, p1 is 0, and q1 is 2 or 3, preferably 3.

[0365] R d1 are each independently -Z 2 -CR 31 p2 R 32 q2 R 33 r2 .

[0366] Z 2 are each independently a single bond, an oxygen atom or a divalent organic group. Among them, the right side of the structure denoted as Z 2 is bonded to (CR 31 p2 R 32 q2 R 33 r2 ).

[0367] In a preferred embodiment, Z 2 is a divalent organic group.

[0368] In a preferred embodiment, Z 2 does not contain a siloxane bond.

[0369] Z 2 is preferably C 1-6 alkylene, -(CH2) z5 -O-(CH2) z6 -(wherein, z5 is an integer from 0 to 6, for example, an integer from 1 to 6, and z6 is an integer from 0 to 6, for example, an integer from 1 to 6) or -(CH2) z7 -phenylene-(CH2)z8 -(wherein, z7 is an integer from 0 to 6, for example, an integer from 1 to 6, and z8 is an integer from 0 to 6, for example, an integer from 1 to 6). Such C 1-6 alkylene group can be straight-chain or branched-chain, and is preferably straight-chain. These groups can be substituted with one or more substituents selected from, for example, fluorine atom, C 1-6 alkyl group, C 2-6 alkenyl group and C 2-6 alkynyl group, but is preferably unsubstituted.

[0370] In a preferred embodiment, Z 2 is C 1-6 alkylene group or -(CH2) z7 -phenylene-(CH2) z8 -, preferably -phenylene-(CH2) z8 -. When Z 2 is such a group, the light resistance, especially the ultraviolet resistance, can be further improved.

[0371] In another preferred embodiment, the above-mentioned Z 2 is C 1-3 alkylene group. In one embodiment, Z 2 can be -CH2CH2CH2-. In another embodiment, Z 2 can be -CH2CH2-.

[0372] R 31 are each independently -Z 2' -CR 32' q2' R 33' r2' .

[0373] Z 2' are each independently a single bond, an oxygen atom or a divalent organic group. Among them, the right side of the structure denoted as Z 2' is bonded to (CR 32' q2' R 33' r2' ).

[0374] In a preferred embodiment, Z 2' does not contain a siloxane bond.

[0375] Z 2' is preferably C 1-6 alkylene group, -(CH2) z5' -O-(CH2) z6' -(wherein, z5' is an integer from 0 to 6, for example, an integer from 1 to 6, and z6' is an integer from 0 to 6, for example, an integer from 1 to 6) or -(CH2) z7'-phenylene-(CH2) z8' -(wherein, z7' is an integer from 0 to 6, such as an integer from 1 to 6, and z8' is an integer from 0 to 6, such as an integer from 1 to 6). Such a C 1-6 alkylene group can be straight-chain or branched-chain, preferably straight-chain. These groups can be substituted by one or more substituents selected from, for example, a fluorine atom, C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl, but is preferably unsubstituted.

[0376] In a preferred embodiment, Z 2' is C 1-6 alkylene or -(CH2) z7' -phenylene-(CH2) z8' -, preferably -phenylene-(CH2) z8' -. When Z 2' is such a group, the light resistance, especially the ultraviolet resistance, can be further improved.

[0377] In another preferred embodiment, the above Z 2' is C 1-3 alkylene. In one embodiment, Z 2' can be -CH2CH2CH2-. In another embodiment, Z 2' can be -CH2CH2-.

[0378] R 32' are each independently -Z 3 -SiR 34 n2 R 35 3-n2 .

[0379] Z 3 are each independently a single bond, an oxygen atom, or a divalent organic group. Among them, the right side of the structure denoted as Z 3 is bonded to (SiR 34 n2 R 35 3-n2 ).

[0380] In one embodiment, Z 3 is an oxygen atom.

[0381] In one embodiment, Z 3 is a divalent organic group.

[0382] In a preferred embodiment, Z 3 does not contain a siloxane bond.

[0383] Z 3 is preferably C1-6 Alkylene, -(CH2) z5” -O-(CH2) z6” -(wherein, z5” is an integer from 0 to 6, such as an integer from 1 to 6, and z6” is an integer from 0 to 6, such as an integer from 1 to 6) or -(CH2) z7” -Arylene-(CH2) z8” -(wherein, z7” is an integer from 0 to 6, such as an integer from 1 to 6, and z8” is an integer from 0 to 6, such as an integer from 1 to 6). Such C 1-6 Alkylene can be straight-chain or branched-chain, preferably straight-chain. These groups can be substituted with one or more substituents selected from, for example, a fluorine atom, C 1-6 Alkyl, C 2-6 Alkenyl and C 2-6 Alkynyl, but is preferably unsubstituted.

[0384] In a preferred embodiment, Z 3 is C 1-6 Alkylene or -(CH2) z7” -Arylene-(CH2) z8 ”- and is preferably -Arylene-(CH2) z8” -. When Z 3 is such a group, the light resistance, especially the ultraviolet resistance, can be further improved.

[0385] In another preferred embodiment, the above Z 3 is C 1-3 Alkylene. In one embodiment, Z 3 can be -CH2CH2CH2-. In another embodiment, Z 3 can be -CH2CH2-.

[0386] R 34 are each independently a hydroxyl group or a hydrolyzable group.

[0387] R 34 are preferably each independently a hydrolyzable group.

[0388] R 34 are preferably each independently -OR h -, -OCOR h -, -O-N=CR h 2, -NR h 2, -NHR h -, -NCO or a halogen (in these formulas, R h represents a substituted or unsubstituted C 1-4 alkyl), and more preferably -OR h (i.e., an alkoxy group). As R h, examples include: non-substituted alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, and isobutyl; and substituted alkyl groups such as chloromethyl. Among these, alkyl groups, particularly non-substituted alkyl groups, are preferred, and methyl or ethyl is more preferred. In one embodiment, R h is methyl, and in another embodiment, R h is ethyl.

[0389] R 35 are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups other than the above hydrolyzable groups.

[0390] In R 35 , the monovalent organic group is preferably a C 1-20 alkyl group, more preferably a C 1-6 alkyl group, and further preferably methyl.

[0391] n2 is each independently an integer from 0 to 3 in each (SiR 34 n2 R 35 3-n2 ) unit. Among them, at the terminal portion of formula (S4), at least 2 (SiR 34 n2 R 35 3-n2 ) units with n2 being an integer from 1 to 3 are present. In other words, at the terminal portion of formula (S4), at least 2 Si atoms bonded to a hydroxyl group or a hydrolyzable group are present.

[0392] n2 is each independently preferably an integer from 1 to 3, more preferably 2 to 3, and further preferably 3 in each (SiR 34 n2 R 35 3-n2 ) unit.

[0393] R 33' are each independently a hydrogen atom, a hydroxyl group, or a monovalent organic group. Such monovalent organic groups are monovalent organic groups other than the above hydrolyzable groups.

[0394] In R 33' , the monovalent organic group is preferably a C 1-20 alkyl group or -(C s H 2s ) t1 -(O-C s H 2s ) t2 (wherein s is an integer from 1 to 6, preferably an integer from 2 to 4, t1 is 1 or 0, preferably 0, and t2 is an integer from 1 to 20, preferably an integer from 2 to 10, and more preferably an integer from 2 to 6), and more preferably a C 1-20Alkyl, more preferably C 1-6 alkyl, particularly preferably methyl.

[0395] In one embodiment, R 33' is a hydroxyl group.

[0396] In another embodiment, R 33' is a monovalent organic group, preferably C 1-20 alkyl, more preferably C 1-6 alkyl.

[0397] The above q2' are each independently an integer from 0 to 3, and the above r2' are each independently an integer from 0 to 3. Among them, the sum of q2' and r2' is 3 in the (CR 32' q2' R 33' r2' ) unit.

[0398] q2' is each independently preferably an integer from 1 to 3, more preferably 2 to 3, and even more preferably 3 in each (CR 32' q2' R 33' r2' ) unit.

[0399] R 32 are each independently -Z 3 -SiR 34 n2 R 35 3-n2 . Such -Z 3 -SiR 34 n2 R 35 3-n2 has the same meaning as described above for R 32' .

[0400] R 33 are each independently a hydrogen atom, a hydroxyl group, or a monovalent organic group. Such a monovalent organic group is a monovalent organic group other than the above hydrolyzable groups.

[0401] In R 33 , the monovalent organic group is preferably C 1-20 alkyl or -(C s H 2s ) t1 -(O-C s H 2s ) t2 (wherein s is an integer from 1 to 6, preferably an integer from 2 to 4, t1 is 1 or 0, preferably 0, t2 is an integer from 1 to 20, preferably an integer from 2 to 10, and more preferably an integer from 2 to 6), more preferably C 1-20An alkyl group, more preferably a C 1-6 alkyl group, particularly preferably a methyl group.

[0402] In one embodiment, R 33 is a hydroxyl group.

[0403] In another embodiment, R 33 is a monovalent organic group, preferably a C 1-20 alkyl group, more preferably a C 1-6 alkyl group.

[0404] p2 are each independently an integer from 0 to 3, q2 are each independently an integer from 0 to 3, and r2 are each independently an integer from 0 to 3. Among them, the sum of p2, q2, and r2 is 3 in the (CR 31 p2 R 32 q2 R 33 r2 ) unit.

[0405] In one embodiment, p2 is 0.

[0406] In one embodiment, p2 can be each independently an integer from 1 to 3, an integer from 2 to 3, or 3 in each (CR 31 p2 R 32 q2 R 33 r2 ) unit. In a preferred embodiment, p2 is 3.

[0407] In one embodiment, q2 is each independently an integer from 1 to 3, preferably an integer from 2 to 3, more preferably 3 in each (CR 31 p2 R 32 q2 R 33 r2 ) unit.

[0408] In one embodiment, p2 is 0, and q2 is each independently an integer from 1 to 3, preferably an integer from 2 to 3, more preferably 3 in each (CR 31 p2 R 32 q2 R 33 r2 ) unit.

[0409] R e1 are each independently -Z 3 -SiR 34 n2 R 35 3-n2 . Such -Z3 -SiR 34 n2 R 35 3-n2 has the same meaning as R described above 32' in the above description

[0410] R f1 is independently a hydrogen atom, a hydroxyl group or a monovalent organic group. Such a monovalent organic group is a monovalent organic group other than the above hydrolyzable groups

[0411] In R f1 the monovalent organic group is preferably a C 1-20 alkyl group or -(C s H 2s ) t1 -(O-C s H 2s ) t2 (wherein s is an integer from 1 to 6, preferably an integer from 2 to 4, t1 is 1 or 0, preferably 0, and t2 is an integer from 1 to 20, preferably an integer from 2 to 10, more preferably an integer from 2 to 6), more preferably a C 1-20 alkyl group, further preferably a C 1-6 alkyl group, particularly preferably a methyl group

[0412] In one embodiment, R f1 is a hydroxyl group

[0413] In another embodiment, R f1 is a monovalent organic group, preferably a C 1-20 alkyl group, more preferably a C 1-6 alkyl group

[0414] k2 are each independently an integer from 0 to 3, l2 are each independently an integer from 0 to 3, and m2 are each independently an integer from 0 to 3. Among them, the sum of k2, l2 and m2 is 3 in the (CR d1 k2 R e1 l2 R f1 m2 ) unit

[0415] In one embodiment, n2 is 1 to 3, preferably 2 or 3, more preferably 3, and two or more, for example, 2 to 27, preferably 2 to 9, more preferably 2 to 6, further preferably 2 to 3, particularly preferably 3, of the (SiR 34 n2 R 35 3 - n2 ) units are present at each end portion of formula (S4)

[0416] In a preferred embodiment, when R exists in formula (S4) 32' at least one, preferably all of the R 32' wherein n2 is an integer from 1 to 3, preferably 2 or 3, more preferably 3.

[0417] In a preferred embodiment, when R exists in formula (S4) 32 at least one, preferably all of the R 32 wherein n2 is an integer from 1 to 3, preferably 2 or 3, more preferably 3.

[0418] In a preferred embodiment, when R exists in formula (S4) e1 at least one, preferably all of the R a1 wherein n2 is an integer from 1 to 3, preferably 2 or 3, more preferably 3.

[0419] In a preferred embodiment, in formula (S4), k2 is 0, l2 is 2 or 3, preferably 3, and n2 is 2 or 3, preferably 3.

[0420] R g1 and R h1 are each independently -Z 4 -SiR 11 n1 R 12 3-n1 、-Z 4 -SiR a1 k1 R b1 l1 R c1 m1 、-Z 4 -CR d1 k2 R e1 l2 R f1 m2 . Herein, the meanings of R 11 , R 12 , R a1 , R b2 , R c1 , R d1 , R e1 , R f1 , n1, k1, l1, m1, k2, l2 and m2 are the same as defined above.

[0421] In a preferred embodiment, R g1 and R h1 are each independently -Z 4 -SiR 11 n1 R 12 3-n1 .

[0422] The above Z 4 is independently a single bond, an oxygen atom or a divalent organic group, respectively. Among them, Z denoted below 4 the right side of the structure of is bonded to (SiR 11 n1 R 12 3-n1 ) bond.

[0423] In one embodiment, Z 4 is an oxygen atom.

[0424] In one embodiment, Z 4 is a divalent organic group.

[0425] In a preferred embodiment, Z 4 does not contain a siloxane bond.

[0426] Z 4 is preferably C 1-6 alkylene, -(CH2) z5” -O-(CH2) z6” -(wherein, z5'' is an integer from 0 to 6, such as an integer from 1 to 6, and z6'' is an integer from 0 to 6, such as an integer from 1 to 6) or -(CH2) z7” -substituted phenyl-(CH2) z8” -(wherein, z7'' is an integer from 0 to 6, such as an integer from 1 to 6, and z8'' is an integer from 0 to 6, such as an integer from 1 to 6). Such C 1-6 alkylene can be straight-chain or branched-chain, preferably straight-chain. These groups can be substituted by one or more substituents selected from, for example, a fluorine atom, C 1-6 alkyl, C 2-6 alkenyl and C 2-6 alkynyl, preferably unsubstituted.

[0427] In a preferred embodiment, Z 4 is C 1-6 alkylene or -(CH2) z7” -substituted phenyl-(CH2) z8” -, preferably -substituted phenyl-(CH2) z8” -. When Z 3 is such a group, the light resistance, especially the ultraviolet resistance, can be further improved.

[0428] In another preferred embodiment, the above Z 4 is C 1-3 alkylene. In one embodiment, Z 4 can be -CH2CH2CH2-. In another embodiment, Z 4 can be -CH2CH2-.

[0429] In one embodiment, the formulas (S1), (S2), (S3), (S4) and (S5) do not contain a siloxane bond.

[0430] In one embodiment, R Si is a group represented by formula (S2), (S3), (S4) or (S5).

[0431] In one embodiment, R Si is a group represented by formula (S3), (S4) or (S5).

[0432] In one embodiment, R Si is a group represented by formula (S1). In a preferred embodiment, formula (S1) is a group represented by formula (S1-b). In a preferred embodiment, in the formula, R 13 is a hydrogen atom, X 11 is a single bond or -R 28 -O x -R 29 -(wherein, R 28 and R 29 are each independently a single bond or C 1-20 alkylene, x is 0 or 1), n1 is 1 to 3, preferably 2 to 3, more preferably 3.

[0433] In one embodiment, R Si is a group represented by formula (S2). In a preferred embodiment, formula (S2) is -SiR 11 2R 12 or -SiR 11 3.

[0434] In one embodiment, R Si is a group represented by formula (S3). In a preferred embodiment, formula (S3) is -SiR a1 2R c1 or -SiR a1 3, R a1 is -Z 1 -SiR 22 q1 R 23 r1 where Z 1 is C 1-6 alkylene, -(CH2) z1 -O-(CH2) z2 -(wherein, z1 is an integer from 0 to 6, such as an integer from 1 to 6, z2 is an integer from 0 to 6, such as an integer from 1 to 6) or -(CH2) z3 -substituted phenylene-(CH2) z4-(wherein, z3 is an integer from 0 to 6, such as an integer from 1 to 6, and z4 is an integer from 0 to 6, such as an integer from 1 to 6), preferably C 1-6 alkylene, and q1 is from 1 to 3, preferably from 2 to 3, more preferably 3.

[0435] In one embodiment, R Si is a group represented by formula (S4). In a preferred embodiment, formula (S4) is -CR e1 2R f1 or -CR e1 3, and R e1 is -Z 3 -SiR 34 n2 R 35 3-n2 , Z 3 is C 1-6 alkylene, -(CH2) z5” -O-(CH2) z6” -(wherein, z5” is an integer from 0 to 6, such as an integer from 1 to 6, and z6” is an integer from 0 to 6, such as an integer from 1 to 6) or -(CH2) z7” -arylene-(CH2) z8” -(wherein, z7” is an integer from 0 to 6, such as an integer from 1 to 6, and z8” is an integer from 0 to 6, such as an integer from 1 to 6), preferably C 1-6 alkylene, and n2 is from 1 to 3, preferably from 2 to 3, more preferably 3.

[0436] In one embodiment, R Si is a group represented by formula (S5). In a preferred embodiment, R g1 and R h1 are -Z 4 -SiR 11 n1 R 12 3-n1 , Z 4 is C 1-6 alkylene, -(CH2) z5” -O-(CH2) z6” -(wherein, z5” is an integer from 0 to 6, such as an integer from 1 to 6, and z6” is an integer from 0 to 6, such as an integer from 1 to 6) or -(CH2) z7” -arylene-(CH2) z8” -(wherein, z7” is an integer from 0 to 6, such as an integer from 1 to 6, and z8” is an integer from 0 to 6, such as an integer from 1 to 6), preferably C 1-6 alkylene, and n1 is from 1 to 3, preferably from 2 to 3, more preferably 3.

[0437] In a preferred embodiment, the compound of the present invention may be a silane compound represented by formula (1). In this compound,

[0438] R 1 is R 2 -O-CO-, CH2=CH-, NH2-, or a bromine atom,

[0439] R 2 is methyl,

[0440] X 1 is C 16-26 alkylene,

[0441] X 2 is a single bond, -CO-, or -CONR 41 -,

[0442] R 41 is a hydrogen atom,

[0443] R Si is -SiR 11 3 (wherein R 11 is -OR h 、R h is methyl), -CR e1 3 (wherein R e1 is -Z 3 -SiR 34 3、Z 3 is C3 alkylene, R 34 is -OR h 、R h is methyl) or -NR g1 R h1 (wherein R g1 and R h1 are -Z 4 -SiR 11 3、Z 3 is C3 alkylene, R 11 is -OR h 、R h is methyl) group.

[0444] In a particularly preferred embodiment, the compound of the present invention is the following compound.

[0445]

[0446] (Manufacturing method)

[0447] The compound represented by formula (1) of the present invention can be synthesized, for example, by the following method.

[0448] (Preparation method 1)

[0449] React the compound represented by formula (1a) with the compound represented by formula (1b) to obtain the compound represented by formula (1c). Then, react the compound represented by formula (1c) with the compound represented by formula (A), whereby the silane compound represented by formula (1d) can be obtained.

[0450] HO-CO-X 1' -CH=CH2 (1a)

[0451] [In the formula, X 1' is an alkylene group.]

[0452] R 61 -OH(1b)

[0453] [In the formula, R 61 is a C 1-6 alkyl group.]

[0454] R 61 O-CO-X 1 -CH=CH2 (1c)

[0455] HSiR 63 m R 64 3-m (A)

[0456] [In the formula,

[0457] R 63 are each independently a hydroxyl group or a hydrolyzable group,

[0458] R 64 are each independently a monovalent organic group,

[0459] and m is 1 to 3.]

[0460] R 61 O-CO-X 1 -CH2CH2-SiR 63 m R 64 3-m

[0461] [In the formula, the meanings of the respective symbols are the same as above.]

[0462] (Production method 2)

[0463] React the compound represented by formula (2a) with the compound represented by formula (2b) to obtain the compound represented by formula (2c).

[0464] CH2=CH-X 1' -CO-OH (2a)

[0465] [In the formula, X 1'is an alkylene group.]

[0466] NH2-X 2B' -SiR 63 m R 64 3-m (2b)

[0467] [In the formula,

[0468] X 2B' is an alkylene group,

[0469] R 63 are each independently a hydroxyl group or a hydrolyzable group,

[0470] R 64 are each independently a monovalent organic group,

[0471] m is 1 to 3.]

[0472] CH2=CH-X 1' -CONH-X 2B' -SiR 63 m R 64 3-m (2c)

[0473] [In the formula, the meanings of the symbols are the same as above.]

[0474] (Production method 3)

[0475] React the compound represented by formula (3a) with the compound represented by formula (3b) to obtain the compound represented by formula (3c). Then, react the compound represented by formula (3c) with the compound represented by formula (3d) to obtain the compound represented by formula (3e). Then, react the compound represented by formula (3e) with the compound represented by formula (A) to thereby obtain the silane compound represented by formula (3f).

[0476] HO-CO-X 1' -CO-OH (3a)

[0477] [In the formula, X 1' is an alkylene group.]

[0478] NH2-R 66 -C(R 67 -CH=CH2)3 (3b)

[0479] [In the formula,

[0480] R 66 is a single bond or C 1-12 alkylene group,

[0481] R 67is a single bond or C 1-12 alkylene group.]

[0482] HO-CO-X 1' -CONH-R 66 -C(R 67 -CH=CH2)3 (3c)

[0483] [In the formula, the meanings of the respective symbols are as described above.]

[0484] R 61 -OH (3d)

[0485] [In the formula, R 61 is C 1-6 alkyl group.]

[0486] R 61 O-CO-X 1' -CONH-R 66 -C(R 67 -CH=CH2)3 (3e)

[0487] HSiR 63 m R 64 3-m (A)

[0488] [In the formula,

[0489] R 63 are each independently a hydroxyl group or a hydrolyzable group,

[0490] R 64 are each independently monovalent organic groups,

[0491] and m is 1 to 3.]

[0492] R 61 O-CO-X 1' -CONH-R 66 -C(R 67 -CH2CH2-SiR 63 m R 64 3- m )3 (3f)

[0493] [In the formula, the meanings of the respective symbols are as described above.]

[0494] (Production Method 4)

[0495] Reacting the compound represented by formula (4a) with the compound represented by formula (A) can obtain the silane compound represented by formula (4b).

[0496] R 69 -X1' -CH=CH2 (4a)

[0497] [wherein,

[0498] R 69 is a halogen atom (preferably a bromine atom) or NHR 70 ,

[0499] R 70 is a hydrogen atom or C 1-6 alkyl group,

[0500] X 1' is an alkylene group.]

[0501] HSiR 63 m R 64 3-m (A)

[0502] [wherein,

[0503] R 63 are each independently a hydroxyl group or a hydrolyzable group,

[0504] R 64 are each independently a monovalent organic group,

[0505] m is 1 to 3.]

[0506] R 69 -X 1' -CH2CH2-SiR 63 m R 64 3-m (4b)

[0507] [wherein, the meanings of the symbols are the same as above.]

[0508] (Intermediate)

[0509] The present invention provides an intermediate compound represented by the following formula (2).

[0510] R1-X 1 -R 51 (2)

[0511] [wherein:

[0512] R 1 is R 2 -O-CO-, R 2 -O-C(=O)-O-, R 2 -NR-CO-, R 2 -CO-NR-, R 2 -OCO-NR-, R 2 -NR3 -COO-, R 2 -NR-CO-NR 3 -, CH2=CH-, NHR 3 - or a halogen atom,

[0513] R 2 is a hydrogen atom, C 1-6 alkyl or a group containing an oxyalkylene group having 1 to 30 carbon atoms,

[0514] R 3 is a hydrogen atom or C 1-6 alkyl,

[0515] X 1 is an alkylene group having 12 or more carbon atoms,

[0516] R 51 is the following group:

[0517]

[0518] R 61 is a hydrocarbon group having 1 to 6 carbon atoms,

[0519] * indicates the bonding site.]

[0520] The above hydrocarbon group is preferably an alkyl group having 1 to 6 carbon atoms or an unsaturated hydrocarbon group having 1 to 6 carbon atoms (especially a hydrocarbon group containing a double bond).

[0521] In a preferred embodiment, R 61 is methyl, ethyl, vinyl or allyl.

[0522] The above group containing an oxyalkylene group having 1 to 30 carbon atoms is a group containing -O-C 1-30 alkylene-, for example, -R 81 -( -O-C 1-30 alkylene) n -R 82 (wherein, R 81 is a single bond or a divalent organic group, preferably C 1-6 alkylene, n is an arbitrary integer, preferably an integer of 1 to 10, and R 82 is a hydrogen atom or a monovalent organic group, preferably C 1-6 alkyl, more preferably methyl). The above alkylene may be linear or branched.

[0523] In one embodiment, R 51 can be the following groups.

[0524]

[0525] (Surface treatment agent)

[0526] The present invention provides a surface treatment agent containing the silane compound of the present invention described above.

[0527] The surface treatment agent of the present invention may also contain a condensate of the silane compound of the present invention.

[0528] The surface treatment agent of the present invention may also contain a silane compound containing a Si atom having a hydrolyzable group and not within the scope of the above formula (1).

[0529] In the surface treatment agent of the present invention, the content of the silane compound and its condensate of the present invention may preferably be 60% by mass or more, more preferably 80% by mass or more, further preferably 90% by mass or more, further more preferably 95% by mass or more, and particularly preferably 99% by mass or more, based on all the silane compounds contained in the surface treatment agent.

[0530] In the above manner, the content of the condensate may preferably be 40% by mass or less, more preferably 30% by mass or less, based on the total of the silane compound and the condensate. Here, the content of the condensate can be obtained, for example, from the ratio of the peak position and area in GPC (gel permeation chromatography).

[0531] The above surface treatment agent may contain a solvent, an organosilicon compound (hereinafter referred to as "silicone oil") that can be understood as silicone oil (non-reactive), an amine compound, an alcohol, a catalyst, a surfactant, a polymerization inhibitor, a sensitizer, etc.

[0532] In one aspect, the surface treatment agent of the present invention may contain a solvent selected from R 71 OR 72 、R 73 n8 C6H 6-n8 、R 74 R 75 R 76 Si-(O-SiR 77 R 78 ) m8 -R 79 、(OSiR 77 R 78 ) m9 shown compounds, and a C 1-10 alcohol that may be substituted.

[0533] [In the formula,

[0534] R 71 ~R 79 are each independently a monovalent organic group having 1 to 10 carbon atoms,

[0535] m8 is an integer from 1 to 6,

[0536] m9 is an integer from 3 to 8,

[0537] and n8 is an integer from 0 to 6.]

[0538] The monovalent organic group having 1 to 10 carbon atoms may be linear, branched, or may contain a cyclic structure.

[0539] In one embodiment, the monovalent organic group having 1 to 10 carbon atoms may contain an oxygen atom, a nitrogen atom, or a halogen atom.

[0540] In another embodiment, the monovalent organic group having 1 to 10 carbon atoms does not contain a halogen atom.

[0541] In a preferred embodiment, the monovalent organic group having 1 to 10 carbon atoms is a hydrocarbon group that may be substituted by a halogen, preferably a hydrocarbon group not substituted by a halogen.

[0542] In one embodiment, the hydrocarbon group is linear.

[0543] In another embodiment, the hydrocarbon group is branched.

[0544] In another embodiment, the hydrocarbon group contains a cyclic structure.

[0545] In one embodiment, the solvent is R 71 OR 72 .

[0546] R 71 and R 72 may each independently be preferably a hydrocarbon group having 1 to 8 carbon atoms, more preferably an alkyl group of C 1-6 or a cycloalkyl group of C 5-8 .

[0547] In one embodiment, the solvent is R 73 n8 C6H 6-n8 .

[0548] C6H 6-n8 is an n8-valent benzene ring. That is, R 73 n8 C6H 6-n8 is a benzene substituted by n8 R 73 groups.

[0549] R 73 may each independently be a halogen or an alkyl group of C 1-6 that may be substituted by a halogen.

[0550] n8 is preferably an integer from 1 to 3.

[0551] In one embodiment, the above solvent is R 74 R 75 R 76 Si-(O-SiR 77 R 78 ) m8 -R 79 。

[0552] In one embodiment, the above solvent is (OSiR 77 R 78 ) m9 。(OSiR 77 R 78 ) m9 is a cyclic siloxane formed by the cyclic bonding of multiple OSiR 77 R 78 units.

[0553] R 74 ~R 79 are each independently a hydrogen atom or an alkyl group of C 1-6 , preferably an alkyl group of C 1-6 , more preferably an alkyl group of C1-3, and still more preferably a methyl group.

[0554] m8 is preferably an integer from 1 to 6, more preferably an integer from 1 to 5, and still more preferably 1 to 2.

[0555] m9 is preferably an integer from 3 to 6, more preferably an integer from 3 to 5.

[0556] The substituent of the above-mentioned C 1-10 alcohol that can be substituted can be, for example, a C 1-3 alkoxy group.

[0557] The above-mentioned C 1-10 alcohol that can be substituted can be preferably methanol, ethanol, isopropanol, n-butanol, isobutanol, tert-butanol, sec-butanol, 3-pentanol, octanol, 3-methyl-3-methoxybutanol or tert-pentanol.

[0558] In one mode, examples of the above solvent include: aliphatic hydrocarbons such as hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, and petroleum spirit; aromatic hydrocarbons such as benzene, toluene, xylene, naphthalene, and solvent naphtha; esters such as methyl acetate, ethyl acetate, propyl acetate, n-butyl acetate, isopropyl acetate, isobutyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate, carbitol acetate, diethyl oxalate, ethyl pyruvate, ethyl 2-hydroxybutyrate, ethyl acetoacetate, amyl acetate, methyl lactate, ethyl lactate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 2-hydroxyisobutyrate, and ethyl 2-hydroxyisobutyrate; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, 2-hexanone, cyclohexanone, methyl amino ketone, and 2-heptanone; glycol ethers such as ethyl cellosolve, methyl cellosolve, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, dipropylene glycol dimethyl ether, and ethylene glycol monoalkyl ether; alcohols such as methanol, ethanol, isopropyl alcohol, n-butanol, isobutanol, tert-butanol, sec-butanol, 3-pentanol, octanol, 3-methyl-3-methoxybutanol, and tert-amyl alcohol; glycols such as ethylene glycol and propylene glycol; cyclic ethers such as tetrahydrofuran, tetrahydropyran, and dioxane; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; ether alcohols such as methyl cellosolve, cellosolve, isopropyl cellosolve, butyl cellosolve, and diethylene glycol monomethyl ether; diethylene glycol monoethyl ether acetate; ethers such as cyclopentyl methyl ether; siloxanes such as hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, and tetradecamethylhexasiloxane; fluorinated solvents such as 1,1,2-trichloro-1,2,2-trifluoroethane, 1,2-dichloro-1,1,2,2-tetrafluoroethane, dimethyl sulfoxide, 1,1-dichloro-1,2,2,3,3-pentafluoropropane (HCFC225), ZEORORAH, 1,3-bis(trifluoromethyl)benzene, 1,1,2,3,3,3-hexafluoropropyl methyl ether (CF3CFHCF2OCH3) (HFE-356mec), nonafluorobutyl methyl ether (CF3CF2CF2CF2CF2OCH3) (HFE7100), nonafluorobutyl ethyl ether (CF3CF2CF2CF2CF2OCH2CH3) (HFE7200), 1,1,1,2,3,4,4,5,5,5-decafluoro-2-(trifluoromethyl)pentan-3-yl methyl ether (CF3CF(CF3)CF(OCH3)CF2CF3) (HFE7300), CF3CH2OH, CF3CF2CH2OH, and (CF3)2CHOH. Or, a mixed solvent of two or more of them can be cited. Among them, glycol ethers, alcohols, ether alcohols, and siloxanes are preferred.For example, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, methanol, ethanol, isopropanol, n-butanol, isobutanol, tert-butanol, sec-butanol, diethylene glycol monomethyl ether, hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, tetradecamethylhexasiloxane, octamethylcyclotetrasiloxane, octamethylcyclopentasiloxane are preferred.

[0559] As the silicone oil, there is no particular limitation, and for example, the compound represented by the following general formula (3a) can be cited.

[0560] R 1a -(SiR 3a 2-O) a1 -SiR 3a 2-R 1a ···(3a)

[0561] [In the formula:

[0562] R 1a are each independently a hydrogen atom or a hydrocarbon group,

[0563] R 3a are each independently a hydrogen atom or a hydrocarbon group,

[0564] a1 is from 2 to 3000.]

[0565] R 3a are each independently a hydrogen atom or a hydrocarbon group. Such a hydrocarbon group may be substituted.

[0566] R 3a are each independently preferably an unsubstituted hydrocarbon group or a hydrocarbon group substituted with a halogen atom. Such a halogen atom is preferably a fluorine atom.

[0567] R 3a are each independently preferably a C 1-6 alkyl group or an aryl group that may be substituted with a halogen atom, more preferably a C 1-6 alkyl group or an aryl group.

[0568] The above C 1-6 alkyl group may be straight-chain or branched-chain, preferably straight-chain. The C 1-6 alkyl group is preferably a C 1-3 alkyl group, more preferably a methyl group.

[0569] The above aryl group is preferably a phenyl group.

[0570] In one embodiment, R 3a are each independently a C 1-6 alkyl group, preferably a C 1-3 alkyl group, more preferably a methyl group.

[0571] In another embodiment, R 3ais phenyl.

[0572] In another embodiment, R 3a is methyl or phenyl, preferably methyl.

[0573] R 1a are each independently a hydrogen atom or a hydrocarbon group, having the same meaning as R 3a above.

[0574] R 1a are each independently preferably a C 1-6 alkyl or aryl group which may be substituted by a halogen atom, more preferably a C 1-6 alkyl or aryl group.

[0575] In one embodiment, R 1a are each independently C 1-6 alkyl groups, preferably C 1-3 alkyl groups, more preferably methyl.

[0576] In another embodiment, R 1a is phenyl.

[0577] In another embodiment, R 1a is methyl or phenyl, preferably methyl.

[0578] The above a1 is from 2 to 1500. a1 is preferably 5 or more, more preferably 10 or more, further preferably 15 or more, and for example may be 30 or more or 50 or more. a1 is preferably 1000 or less, more preferably 500 or less, further preferably 200 or less, further more preferably 150 or less, and for example may be 100 or less or 80 or less.

[0579] a1 may preferably be from 5 to 1000, more preferably from 10 to 500, further preferably from 15 to 200, and further more preferably from 15 to 150.

[0580] The above silicone oil may have an average molecular weight of 500 to 1000000, preferably 1000 to 100000. The molecular weight of the silicone oil can be measured using GPC.

[0581] As the above silicone oil, for example, a linear or cyclic silicone oil with a1 of 30 or less represented by -(SiR 3a 2 - O) a1 - can be used. The linear silicone oil can be a so-called ordinary silicone oil and a modified silicone oil. As the ordinary silicone oil, dimethyl silicone oil, methylphenyl silicone oil, and methylhydrogen silicone oil can be cited. As the modified silicone oil, silicone oils obtained by modifying the ordinary silicone oil with alkyl, aralkyl, polyether, higher fatty acid ester, fluoroalkyl, amino, epoxy, carboxyl, alcohol, etc. can be cited. As the cyclic silicone oil, cyclic dimethylsiloxane oil, etc. can be cited, for example.

[0582] The above silicone oil contains, relative to the above surface treatment agent, for example, 0 to 50% by mass, preferably 0.001 to 30% by mass, more preferably 0.1 to 5% by mass.

[0583] In the above surface treatment agent, such a silicone oil can contain, relative to 100 parts by mass in total of the silane compounds of the present invention (when there are two or more kinds, it is their total, the same hereinafter), for example, 0 to 300 parts by mass, preferably 0 to 100 parts by mass, more preferably 0 to 50 parts by mass, and further preferably 0 to 10 parts by mass.

[0584] The silicone oil helps to improve the surface slidability of the surface treatment layer.

[0585] Examples of the above alcohols include methanol, ethanol, isopropyl alcohol, n-butanol, isobutanol, tert-butanol, sec-butanol, 3-pentanol, octanol, 3-methyl-3-methoxybutanol, and tert-pentanol. By adding these alcohols to the surface treatment agent, the stability of the surface treatment agent can be improved.

[0586] Examples of the above catalysts include acids (such as acetic acid, hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, sulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid, etc.), bases (such as sodium hydroxide, potassium hydroxide, ammonia, triethylamine, diethylamine, etc.), transition metals (such as Ti, Ni, Sn, Zr, Al, B, Si, Ta, Nb, Mo, W, Cr, Hf, V, etc.), sulfur-containing compounds having non-bonding electrons in the molecular structure, or nitrogen-containing compounds (such as sulfoxide compounds, aliphatic amine compounds, aromatic amine compounds, phosphoric acid amide compounds, amide compounds, urea compounds), etc.

[0587] Examples of the above aliphatic amine compounds include diethylamine, triethylamine, etc. Examples of the above aromatic amine compounds include aniline, pyridine, etc.

[0588] In a preferred embodiment, the above transition metal is contained in the form of a transition metal compound represented by M-R (wherein M is a transition metal atom and R is a hydrolyzable group). By using a transition metal compound in which a transition metal is bonded to a hydrolyzable group, the surface treatment layer can contain transition metal atoms more effectively, and the friction durability and chemical resistance of the surface treatment layer can be further improved.

[0589] The above hydrolyzable group refers to a group that can undergo a hydrolysis reaction in the same manner as the hydrolyzable group involved in the above silane compound, that is, a group that can be detached from the transition metal atom through a hydrolysis reaction. Examples of the hydrolyzable group include -OR m , -OCOR m , -O-N=CR m 2, -NR m 2, -NHRm , -NCO or halogen (in these formulas, R m represents a substituted or unsubstituted C 1-4 alkyl), etc.

[0590] In a preferred embodiment, the above hydrolyzable group is -OR m , preferably methoxy or ethoxy. By using an alkoxy group as the hydrolyzable group, the surface treatment layer can more effectively contain transition metal atoms, and the friction durability and chemical resistance of the surface treatment layer can be further improved.

[0591] In one embodiment, the above hydrolyzable group may be the same as the hydrolyzable group contained in the above silane compound. By making the hydrolyzable groups in the silane compound and the transition metal compound the same group, even when these hydrolyzable groups are exchanged with each other, their influence can be reduced.

[0592] In another embodiment, the above hydrolyzable group may also be different from the hydrolyzable group contained in the above silane compound. By making the hydrolyzable groups in the silane compound and the transition metal compound different, the reactivity of hydrolysis can be controlled.

[0593] In one embodiment, the above hydrolyzable group and the hydrolyzable group contained in the above silane compound may be replaceable with each other in the surface treatment agent.

[0594] In a preferred embodiment, the above transition metal compound is Ta(OR m )5 (in the formula, R m is a substituted or unsubstituted C 1-4 alkyl), preferably Ta(OCH2CH3)5 or Si(OR m ) 1-m1 R m' m1 (in the formula, R m is a substituted or unsubstituted C 1-4 alkyl, R m' is C 1-4 alkyl, m1 is 0 or 1), and may preferably be tetraethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, tetraisopropoxysilane, dimethyldiethoxysilane or dimethyldimethoxysilane.

[0595] With respect to the whole surface treatment agent, the content of the above catalyst may be, for example, 0.0002% by mass or more. With respect to the whole surface treatment agent, the content of the above catalyst is preferably 0.02% by mass or more, more preferably 0.04% by mass or more. With respect to the whole surface treatment agent, the content of the above catalyst may be, for example, 10% by mass or less, particularly 1% by mass or less. By containing the above catalyst in the above concentration, the surface treatment agent helps to form a surface treatment layer with better durability.

[0596] The content of the above catalyst is preferably 0 to 10% by mass, more preferably 0 to 5% by mass, and particularly preferably 0 to 1% by mass, relative to the silane compound of the present invention.

[0597] The catalyst promotes the hydrolysis and dehydration condensation of the silane compound of the present invention and promotes the formation of the layer formed by the above surface treatment agent.

[0598] As other components, in addition to the above components, for example, tetraethoxysilane, methyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, methyltriacetoxysilane, etc. can also be cited.

[0599] In the above surface treatment agent, in addition to the above components, as impurities, for example, trace amounts of Pt, Rh, Ru, 1,3-divinyltetramethyldisiloxane, triphenylphosphine, NaCl, KCl, condensates of silane, etc. may be contained.

[0600] In one mode, the above surface treatment agent is used for the dry coating method, preferably for vacuum evaporation coating.

[0601] In one mode, the above surface treatment agent is used for the wet coating method, preferably for dip coating.

[0602] The above surface treatment agent can be impregnated in a porous material, such as a porous ceramic material, or a material formed by fixing metal fibers, such as steel wool, in a cotton-like shape, to form pellets. These pellets can be used, for example, for vacuum evaporation coating.

[0603] (Article)

[0604] Hereinafter, the article of the present invention will be described.

[0605] The article of the present invention includes a substrate and a layer (surface treatment layer) formed on the surface of the substrate by the surface treatment agent of the present invention.

[0606] Substrates that can be used in the present invention can be composed of, for example, glass, resin (natural or synthetic resin, for example, can be common plastic materials), metal, ceramic, semiconductor (such as silicon, germanium, etc.), fiber (fabric, non-woven fabric, etc.), fur, leather, wood, ceramics, stone, etc., building materials, sanitary products, any suitable materials.

[0607] For example, in the case where the article to be manufactured is an optical component, the material constituting the surface of the substrate may be a material for optical components, such as glass or transparent plastic, etc. Additionally, in the case where the article to be manufactured is an optical component, a certain layer (or film) may also be formed on the surface (outermost layer) of the substrate, such as a hard coat or an antireflection layer, etc. The antireflection layer can be any one of a single-layer antireflection layer and a multilayer antireflection layer. As examples of inorganic substances that can be used as the antireflection layer, SiO2, SiO, ZrO2, TiO2, TiO, Ti2O3, Ti2O5, Al2O3, Ta2O5, Ta3O5, Nb2O5, HfO2, Si3N4, CeO2, MgO, Y2O3, SnO2, MgF2, WO3, etc. can be cited. These inorganic substances can be used alone, or two or more of them can be combined (for example, to form a mixture) and used. In the case of forming a multilayer antireflection layer, it is preferable to use SiO2 and / or SiO in its outermost layer. In the case where the article to be manufactured is an optical glass component for a touch panel, a transparent electrode may be provided on a part of the surface of the substrate (glass), for example, a thin film of indium tin oxide (ITO) or indium zinc oxide, etc. is used. Additionally, in the substrate, depending on its specific specifications, etc., an insulating layer, an adhesive layer, a protective layer, a decorative frame layer (I-CON), a fogging film layer, a hard coat film layer, a polarizing film, a retardation film, and a liquid crystal display module, etc. may also be provided.

[0608] The shape of the above-mentioned substrate is not particularly limited, and for example, it can be in the form of a plate, a film, or other forms. Additionally, the surface area of the substrate on which the surface treatment layer is to be formed only needs to be at least a part of the substrate surface, and can be appropriately determined according to the use and specific specifications of the article to be manufactured, etc.

[0609] In one mode, as such a substrate, at least a surface portion thereof can be formed of a material that inherently has hydroxyl groups. As such materials, glass can be cited, and metals (especially base metals), ceramics, semiconductors, etc. that can form a natural oxide film or a thermal oxide film on the surface can also be cited. Or, in the case of a resin, etc., when the hydroxyl groups are insufficient or not present originally, by performing a certain pretreatment on the substrate, hydroxyl groups can be introduced onto the surface of the substrate or the hydroxyl groups can be increased. As examples of such pretreatment, plasma treatment (such as corona discharge) or ion beam irradiation can be cited. In order to be able to introduce hydroxyl groups onto the substrate surface or increase the hydroxyl groups and purify the substrate surface (remove foreign substances, etc.), plasma treatment is also suitable. Additionally, as other examples of such pretreatment, the following methods can be cited: using the LB method (Langmuir-Blodgett method) or chemical adsorption method, etc., a surface adsorbent having a carbon-carbon unsaturated bond group is pre-formed in the form of a monolayer film on the substrate surface, and then, in an atmosphere containing oxygen and nitrogen, etc., the unsaturated bond is broken.

[0610] In another mode, as such a substrate, at least its surface portion may be formed of an organosilicon compound having one or more other reactive groups, such as an Si—H group, or a material containing an alkoxysilane.

[0611] In a preferred mode, the above-mentioned substrate is glass. As such glass, sapphire glass, soda-lime glass, alkali aluminosilicate glass, borosilicate glass, non-alkali glass, crystal glass, and quartz glass are preferred, and chemically strengthened soda-lime glass, chemically strengthened alkali aluminosilicate glass, and chemically bonded borosilicate glass are particularly preferred.

[0612] In one mode, the article of the present invention may have a silicon oxide-containing intermediate layer between the glass and the surface treatment layer. By providing such an intermediate layer, the adhesion between the glass and the surface treatment layer is improved, and the durability is improved.

[0613] In a preferred mode, the above-mentioned intermediate layer may further contain an alkali metal in addition to containing silicon oxide.

[0614] As the above-mentioned alkali metal, for example, lithium, sodium, potassium, etc. can be cited. The above-mentioned alkali metal is preferably sodium.

[0615] The thickness of the intermediate layer is not particularly limited, and is preferably 1 to 200 nm, particularly preferably 1 to 20 nm. By making the thickness of the intermediate layer above the lower limit value of the above range, the effect of improving the adhesiveness by the intermediate layer is better.

[0616] The concentration of alkali metal atoms in the intermediate layer can be measured by various surface analysis devices, such as TOF-SIMS, XPS, XRF, etc.

[0617] The ratio of alkali metal atoms to all atoms in the entire intermediate layer can be obtained by depth analysis of XPS using ion sputtering, and is carried out by alternately repeating the measurement by XPS and surface etching by ion sputtering using an ion gun built in the XPS apparatus.

[0618] In the intermediate layer, regarding the average value of the alkali metal concentration in the region with a depth of 1 nm or less from the surface in contact with the surface treatment layer, after obtaining the distribution curve of the concentration of alkali metal atoms in the depth direction by depth analysis of TOF-SIMS (time-of-flight secondary ion mass spectrometry) using ion sputtering, the average value of the alkali metal atom concentration on the distribution curve is calculated and obtained. The depth analysis of TOF-SIMS using ion sputtering is carried out by alternately repeating the measurement by TOF-SIMS and surface etching by ion sputtering using an ion gun built in the TOF-SIMS apparatus.

[0619] An article of the present invention can be manufactured by forming a layer of the surface treatment agent of the present invention on the surface of the above-mentioned substrate and then, if necessary, subjecting this layer to post-treatment to form a layer with the surface treatment agent of the present invention.

[0620] The formation of the layer of the surface treatment agent of the present invention can be carried out by applying the above-mentioned surface treatment agent to the surface in a manner that covers the substrate surface. The covering method is not particularly limited. For example, a wet covering method and a dry covering method can be used.

[0621] Examples of the wet covering method include dip coating, spin coating, flow coating, spray coating, roll coating, gravure coating, wipe coating, squeegee coat method, die coating, inkjet, casting method, Langmuir-Blodgett method, and similar methods.

[0622] Examples of the dry covering method include vapor deposition (usually vacuum vapor deposition), sputtering, CVD, and similar methods. Specific examples of the vapor deposition method (usually the vacuum vapor deposition method) include resistance heating, electron beam, high-frequency heating using microwaves, ion beam, and similar methods. Specific examples of the CVD method include plasma-CVD, optical CVD, thermal CVD, and similar methods.

[0623] In addition, covering using the atmospheric pressure plasma method can also be used.

[0624] In the case of using the wet covering method, the surface treatment agent of the present invention can be diluted with a solvent and applied to the surface of a substrate. From the viewpoints of the stability of the composition of the present invention and the volatility of the solvent, the following solvents are preferably used: aliphatic hydrocarbons such as hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, and mineral spirits; aromatic hydrocarbons such as benzene, toluene, xylene, naphthalene, and solvent naphtha; esters such as methyl acetate, ethyl acetate, propyl acetate, n-butyl acetate, isopropyl acetate, isobutyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate, carbitol acetate, diethyl oxalate, ethyl pyruvate, ethyl 2-hydroxybutyrate, ethyl acetoacetate, amyl acetate, methyl lactate, ethyl lactate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 2-hydroxyisobutyrate, and ethyl 2-hydroxyisobutyrate; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, 2-hexanone, cyclohexanone, methylamino ketone, and 2-heptanone; glycol ethers such as ethyl cellosolve, methyl cellosolve, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, dipropylene glycol dimethyl ether, and ethylene glycol monoalkyl ether; alcohols such as methanol, ethanol, isopropyl alcohol, n-butanol, isobutanol, tert-butanol, sec-butanol, 3-pentanol, octanol, 3-methyl-3-methoxybutanol, and tert-amyl alcohol; glycols such as ethylene glycol and propylene glycol; cyclic ethers such as tetrahydrofuran, tetrahydropyran, and dioxane; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; ether alcohols such as methyl cellosolve, cellosolve, isopropyl cellosolve, butyl cellosolve, and diethylene glycol monomethyl ether; diethylene glycol monoethyl ether acetate; polyfluoroaromatic hydrocarbons (such as 1,3-bis(trifluoromethyl)benzene); polyfluoroaliphatic hydrocarbons (such as C6F 13CH2CH3 (such as ASAHIKLIN (registered trademark) AC-6000 produced by Asahi Glass Co., Ltd.), 1,1,2,2,3,3,4-heptafluorocyclopentane (such as ZEORORA (registered trademark) H produced by ZEON CORPORATION); hydrofluoroether (HFE) (such as perfluoropropyl methyl ether (C3F7OCH3) (such as Novec (trademark) 7000 produced by Sumitomo 3M Limited), perfluorobutyl methyl ether (C4F9OCH3) (such as Novec (trademark) 7100 produced by Sumitomo 3M Limited), perfluorobutyl ethyl ether (C4F9OC2H5) (such as Novec (trademark) 7200 produced by Sumitomo 3M Limited), perfluorohexyl methyl ether (C2F5CF(OCH3)C3F7) (such as Novec (trademark) 7300 produced by Sumitomo 3M Limited), etc. alkyl perfluoroalkyl ethers (the perfluoroalkyl and alkyl can be straight-chain or branched-chain), or CF3CH2OCF2CHF2 (such as ASAHIKLIN (registered trademark) AE-3000 produced by Asahi Glass Co., Ltd.) and ether alcohols such as cyclopentyl methyl ether; siloxanes such as hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, octamethylcyclotetrasiloxane, octamethylcyclopentasiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, tetradecamethylhexasiloxane, etc. These solvents can be used alone or in the form of a mixture of two or more. Among them, glycol ethers, alcohols, ether alcohols, and siloxanes are preferred. For example, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, methanol, ethanol, isopropanol, n-butanol, isobutanol, tert-butanol, sec-butanol, diethylene glycol monomethyl ether, hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, tetradecamethylhexasiloxane, octamethylcyclotetrasiloxane, octamethylcyclopentasiloxane are particularly preferred.

[0625] In the case of using the dry coating method, the surface treatment agent of the present invention can be directly applied to the dry coating method, or can also be applied to the dry coating method after being diluted with the above-mentioned solvent.

[0626] The formation of the layer of the surface treatment agent is preferably carried out in such a way that the surface treatment agent of the present invention coexists with a catalyst for hydrolysis and dehydration condensation in the layer. In short, in the case of using the wet coating method, after diluting the surface treatment agent of the present invention with a solvent, before applying it to the surface of the substrate, a catalyst can be added to the diluted solution of the surface treatment agent of the present invention. In the case of using the dry coating method, the surface treatment agent of the present invention after adding the catalyst can be directly subjected to evaporation coating (usually vacuum evaporation coating), or the surface treatment agent of the present invention after adding the catalyst can be impregnated in a metal porous body such as iron or copper to obtain a granular substance, and the obtained granular substance is used for evaporation coating (usually vacuum evaporation coating) treatment.

[0627] The catalyst can be any suitable acid or base, transition metal (such as Ti, Ni, Sn, Zr, Al, B, etc.), sulfur-containing compound having a non-bonding electron pair in the molecular structure, or nitrogen-containing compound (such as sulfoxide compound, aliphatic amine compound, aromatic amine compound, phosphoric acid amide compound, amide compound, urea compound), etc. As the acid catalyst, for example, acetic acid, formic acid, trifluoroacetic acid, hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, sulfonic acid, methanesulfonic acid, p-toluenesulfonic acid, etc. can be used. In addition, as the base catalyst, for example, ammonia, sodium hydroxide, potassium hydroxide, organic amines such as triethylamine, diethylamine, etc. can be used. The same substances as those described above can be cited for the transition metal, aliphatic amine compound and aromatic amine compound.

[0628] The surface treatment layer included in the article of the present invention has both high wear durability and fingerprint wiping property. In addition, in addition to high wear durability, the above surface treatment layer can also have water repellency, oil repellency, antifouling property (such as preventing the attachment of stains such as fingerprints), waterproof property (preventing water from infiltrating into electronic components, etc.), surface slidability (or lubricity, such as the wiping property of stains such as fingerprints, excellent finger touch), chemical resistance, etc., depending on the composition of the surface treatment agent used, and is suitable for use as a functional film.

[0629] Therefore, the present invention also relates to an optical material having the above surface treatment layer on the outermost layer.

[0630] As the optical material, in addition to the optical materials related to displays as exemplified below, various optical materials are preferably cited, such as: cathode ray tubes (CRT, such as computer monitors), liquid crystal displays, plasma displays, organic EL displays, inorganic thin film EL dot matrix displays, rear projection type displays, fluorescent display tubes (VFD), field emission displays (FED, Field Emission Display), etc. displays or protective plates of these displays, or materials having an antireflection film treatment on the surface thereof.

[0631] The article of the present invention is not particularly limited and can be an optical component. Examples of the optical component can be cited as follows: lenses for glasses, etc.; front protective plates, antireflection plates, polarizing plates, antiglare plates of displays such as PDP, LCD, etc.; touch panel sheets of devices such as mobile phones, portable information terminals, etc.; disk surfaces of Blu-ray (registered trademark) discs, DVD discs, CD-R, MO, etc.; optical fibers; display surfaces of watches, etc.

[0632] In addition, the article of the present invention may also be a medical device or medical material. In addition, an article having the layer obtained by the present invention may also be an interior or exterior automotive material. Examples of the exterior material may include the following: window, lamp cover, and outside vehicle camera cover. Examples of the interior material may include the following: instrument panel cover, navigation system touch panel, and decorative interior material.

[0633] The thickness of the above layer is not particularly limited. In the case of an optical component, from the viewpoints of optical performance, wear durability, and antifouling property, it is preferable that the thickness of the above layer is, for example, in the range of 1 to 50 nm, preferably 1 to 30 nm, more preferably 1 to 15 nm.

[0634] The above-mentioned silica-containing intermediate layer can be formed by applying a silica precursor to the surface of a substrate. In the case where the intermediate layer contains an alkali metal, the above-mentioned intermediate layer can be formed by applying a composition containing a silica precursor and an alkali metal source to the surface of a substrate.

[0635] Examples of the above silica precursor include silicic acid, partial condensates of silicic acid, alkali metal silicates, silane compounds having a hydrolyzable group bonded to a silicon atom, and partial hydrolysis condensates of the silane compounds. Silicic acid or its partial condensates can be dehydrated and condensed to form silica; alkali metal silicates can form silicic acid or its partial condensates by using an acid or a cation exchange resin, and the resulting silicic acid or its partial condensates can be dehydrated and condensed to form silica. Examples of the hydrolyzable group in the silane compound having a hydrolyzable group bonded to a silicon atom include an alkoxy group and a chlorine atom. By hydrolyzing the hydrolyzable group of the silane compound to form a hydroxyl group and dehydrating and condensing the resulting silanol compound, silica can be formed. Examples of the silane compound having a hydrolyzable group bonded to a silicon atom include alkoxysilanes such as tetraalkoxysilane and alkyltrialkoxysilane, and silicon tetrachloride.

[0636] Examples of the above alkali metal source include alkali metal hydroxides and water-soluble alkali metal salts. Examples of the water-soluble alkali metal salts include alkali metal carbonates, alkali metal hydrogencarbonates, alkali metal hydrochlorides, and alkali metal nitrates. As the alkali metal source, alkali metal hydroxides and alkali metal carbonates are preferable.

[0637] Among them, alkali metal silicates can be used as both a silica precursor and an alkali metal source. Although alkali metal silicates can form silica via silicic acid, a small amount of alkali metal will remain in the resulting silica. Therefore, by adjusting the amount of the remaining alkali metal, silica containing a specified amount of alkali metal atoms can be obtained.

[0638] The thickness of the above intermediate layer is not particularly limited, and is, for example, in the range of 1 to 50 nm, preferably 1 to 30 nm, more preferably 2 to 15 nm, and further preferably 3 to 10 nm.

[0639] The compounds, surface treatment agents, and articles of the present invention have been described in detail above. However, the compounds, surface treatment agents, articles, etc. of the present invention are not limited to the examples illustrated above.

[0640] Examples

[0641] Hereinafter, the present invention will be described in the examples, but the present invention is not limited to the following examples.

[0642] Synthesis Example 1

[0643] 22-Tricosenoic acid (1.999 g), toluene (17 mL), and methanol (11 mL) were added to a flask, and trimethylsilyldiazomethane (11 mL, 0.6 mol / L hexane solution) was added dropwise, and the mixture was stirred at room temperature overnight. Then, concentration under reduced pressure was performed to obtain CH3OCO(CH2) 20 CH=CH2 (2.10 g, Compound A).

[0644] Compound A

[0645]

[0646] 1 H-NMR (CDCl3, 400 MHz) δ [ppm]: 1.25 - 1.40 (m), 1.58 - 1.65 (m), 2.01 - 2.06 (m), 2.28 - 2.32 (t), 3.66 (s), 4.90 - 5.02 (m), 5.76 - 5.86 (m)

[0647] CH3OCO(CH2) was added 20 CH=CH2 (2.10 g, Compound A), toluene (28 mL), pyridine (0.1 mL), Karstedt's catalyst (0.1 mL, xylene solution containing 2% platinum), and trimethoxysilane (2.15 mL) were added, and the mixture was stirred at room temperature overnight. Then, purification was performed to obtain CH3OCO(CH2) having a trimethoxysilyl group at the terminal 22 Si(OCH3)3 (2.63 g, Compound B).

[0648] Compound B

[0649]

[0650] 1 H-NMR (CDCl3, 400 MHz) δ [ppm]: 0.62 - 0.66 (m), 1.24 - 1.47 (m), 1.57 - 1.16 (m), 2.27 - 2.31 (m), 3.56 (s), 3.67 (s)

[0651] Synthesis Example 2

[0652] Add 22 - tricosenoic acid (1 g), thionyl chloride (4.0 g) and N,N - dimethylformamide (2 mg) to a flask, heat to 50 °C and stir for 2 hours. After concentration under reduced pressure, add toluene (10 mL) and triethylamine (0.31 g), cool to below 5 °C, add 3 - aminopropyltrimethoxysilane (0.56 g), and stir at room temperature for 18 hours. Add chloroform and water to the resulting reaction product, transfer to a separatory funnel, remove the aqueous layer after separation, and wash the organic layer with water twice. Add anhydrous sodium sulfate to the organic layer, stir, filter, and concentrate the filtrate to obtain CH2=CH(CH2) 20 CONHCH2CH2CH2Si(OCH3)3 (1.44 g, Compound C).

[0653] Compound C

[0654]

[0655] 1 H-NMR(CDCl3, 400 MHz) δ [ppm]: 0.64 (t, 2H, J = 8.2 Hz), 1.24 - 1.38 (m, 34H), 1.57 - 1.65 (m, 4H), 2.03 (q, 2H, J = 7.0 Hz), 2.14 (t, 2H, J = 7.5 Hz), 3.24 (q, 2H, J = 6.6 Hz), 3.59 (s, 9H), 4.90 - 5.00 (m, 2H), 5.68 (s, 1H), 5.75 - 5.85 (m, 1H)

[0656] Synthesis Example 3

[0657] Add octadecanedioic acid (5.3 g), 2,2 - diallyl - 4 - penten - 1 - amine (5.6 g), 1 - ethyl - 3 - (3 - dimethylaminopropyl)carbodiimide hydrochloride (3.2 g), 4 - dimethylaminopyridine (0.20 g) and tetrahydrofuran (40 mL) to a flask, and stir at 40 °C for 18 hours. Add chloroform and hydrochloric acid and stir, transfer to a separatory funnel, remove the aqueous layer after separation, and wash the organic layer with water twice. Add anhydrous sodium sulfate to the organic layer, stir, filter, and concentrate the filtrate. Purify the white solid of the residue by silica gel column chromatography (developing solvent: chloroform / methanol) to obtain HOCO(CH2) 16 CONHCH2C(CH2CH=CH2)3 (1.01 g, Compound D).

[0658] Compound D

[0659]

[0660] 1 H-NMR (CDCl3, 400 MHz) δ [ppm]: 1.25 (s, 24H), 1.63 (t, 4H, J = 7.1 Hz), 2.02 - 2.09 (m, 6H), 2.17 (t, 2H, J = 7.5 Hz), 2.32 - 2.36 (m, 2H), 3.20 (d, 2H, J = 6.4 Hz), 5.07 - 5.12 (m, 6H), 5.56 (s, 1H), 5.81 - 5.92 (m, 3H)

[0661] HOCO(CH2) 16 CONHCH2C(CH2CH=CH2)3 (0.92 g), trimethylsilyldiazomethane (6.6 mL, 0.6 mol / L hexane solution), methanol (0.64 g) and tetrahydrofuran (9.2 mL) were added to a flask. After stirring at room temperature for 18 hours, concentration under reduced pressure was carried out to obtain CH3OCO(CH2) 16 CONHCH2C(CH2CH=CH2)3 (0.93 g, Compound E).

[0662] Compound E

[0663]

[0664] 1 H-NMR (CDCl3, 400 MHz) δ [ppm]: 1.24 - 1.28 (m, 24H), 1.59 - 1.65 (m, 4H), 2.03 (d, 6H, J = 7.3 Hz), 2.15 (t, 2H, J = 7.5 Hz), 2.29 (t, 2H, J = 7.5 Hz), 3.19 (d, 2H, J = 6.4 Hz), 3.66 (s, 3H), 5.06 - 5.11 (m, 6H), 5.53 (s, 1H), 5.81 - 5.91 (m, 3H)

[0665] CH3OCO(CH2) 16 CONHCH2C(CH2CH=CH2)3 (0.93 g), Karstedt's catalyst (0.38 g, xylene solution containing 2% platinum), trimethoxysilane (2.15 g), pyridine (0.06 g) and toluene (10 mL) were added to a flask. After stirring at room temperature for 4 hours, concentration under reduced pressure was carried out to obtain CH3OCO(CH2) 16 CONHCH2C(CH2CH2CH2Si(OCH3)3)3 (1.10 g, Compound F).

[0666] Compound F

[0667]

[0668] 1 H-NMR (CDCl3, 400 MHz) δ [ppm]: 0.58 - 0.65 (t, 6H), 1.05 - 1.20 (m, 6H), 1.20 - 1.45 (m, 30H), 1.45 - 1.80 (m, 6H), 2.10 - 2.25 (m, 2H), 2.25 - 2.35 (m, 2H), 3.05 - 3.20 (d, 2H), 3.50 - 3.62 (m, 27H), 3.63 - 3.70 (m, 3H), 5.50 - 5.70 (s, 1H)

[0669] Synthesis Example 4

[0670] 18-Amino-1-octadecene (1.0 g), Karstedt's catalyst (0.24 g, xylene solution containing 2% platinum), trimethoxysilane (1.37 g), pyridine (0.04 g) and toluene (10 mL) were added to a flask. After stirring at room temperature for 4 hours, concentration under reduced pressure was carried out to obtain NH2(CH2) 18 Si(OCH3)3 (1.16 g, Compound G).

[0671] Compound G

[0672]

[0673] 1 H-NMR (CDCl3, 400 MHz) δ [ppm]: 0.63 - 0.67 (m, 2H), 1.25 - 1.43 (m, 34H), 2.68 (t, 2H, J = 6.9 Hz), 3.57 - 3.58 (m, 9H)

[0674] 18-Bromo-1-octadecene (1.0 g), Karstedt's catalyst (0.29 g, xylene solution containing 2% platinum), trimethoxysilane (2.21 g), dimethyl sulfoxide (0.03 g), toluene (10 mL) were added to a flask. After stirring at room temperature for 4 hours, concentration under reduced pressure was carried out to obtain Br(CH2) 18 Si(OCH3)3 (1.14 g, Compound H).

[0675] Compound H

[0676]

[0677] 1H-NMR (CDCl3, 400 MHz) δ [ppm]: 0.62 - 0.66 (m, 2H), 1.25 - 1.44 (m, 30H), 1.82 - 1.89 (m, 2H), 3.40 (t, 2H, J = 6.9 Hz), 3.57 - 3.57 (m, 9H)

[0678] Synthesis Example 6

[0679] Add 22 - tricosenoic acid (0.609 g), 1 - ethyl - 3 - (3 - dimethylaminopropyl) carbodiimide hydrochloride (0.545 g), 4 - dimethylaminopyridine (0.02 g), dichloromethane (9 mL) and 3 - methyl - 1 - butanol (0.37 mL) into a flask and stir overnight at room temperature. Then, wash with aqueous hydrochloric acid to obtain CH3CHCH3CH2CH2OCO(CH2) 20 CH=CH2 (0.47 g, Compound I).

[0680] Compound I

[0681]

[0682] 1 H-NMR (CDCl3, 400 MHz) δ [ppm]: 0.91 - 0.93 (m), 1.25 - 1.40 (m), 1.48 - 1.74 (m), 2.01 - 2.06 (q), 2.26 - 2.30 (t), 4.08 - 4.11 (t), 4.91 - 5.02 (m), 5.76 - 5.86 (m)

[0683] Add CH3CHCH3CH2CH2OCO(CH2) 20 CH=CH2 (0.47 g), toluene (3 mL), pyridine (0.1 mL), Karstedt's catalyst (1 mL, xylene solution containing 2% platinum) and trimethoxysilane (0.42 mL) into a flask and stir overnight at room temperature. Then, perform purification to obtain the compound CH3CHCH3CH2CH2OCO(CH2) 22 Si(OCH3)3 (0.51 g, Compound J).

[0684] Compound J

[0685]

[0686] 1H-NMR (CDCl3, 400 MHz) δ [ppm]: 0.02 - 0.14 (m), 0.62 - 0.66 (m), 0.91 - 0.93 (d), 1.25 - 1.28 (m), 1.49 - 1.54 (q), 1.59 - 1.74 (m), 2.26 - 2.30 (t), 3.57 - 3.61 (m), 4.075 - 4.11 (q)

[0687] Synthesis Example 7

[0688] Add 22 - tricosenoic acid (0.601 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.512 g), 4-dimethylaminopyridine (0.02 g), dichloromethane (9 mL) and 2-methyl-1-butanol (0.37 mL) to a flask and stir at room temperature overnight. Then, wash with aqueous hydrochloric acid to obtain CH3CH2CHCH3CH2OCO(CH2) 20 CH=CH2 (0.51 g, Compound K).

[0689] Compound K

[0690]

[0691] 1 H-NMR (CDCl3, 400 MHz) δ [ppm]: 0.86 - 0.93 (m), 1.06 - 1.49 (m), 1.58 - 1.76 (m), 2.01 - 2.06 (q), 2.28 - 2.32 (t), 3.84 - 3.97 (m), 4.91 - 4.02 (m), 5.76 - 5.86 (m)

[0692] Add CH3CH2CHCH3CH2OCO(CH2) 20 CH=CH2 (0.51 g), toluene (3 mL), pyridine (0.1 mL), Karstedt's catalyst (1 mL, xylene solution containing 2% platinum) and trimethoxysilane (0.42 mL) to a flask and stir at room temperature overnight. Then, perform purification to obtain the compound CH3CH2CHCH3CH2OCO(CH2) 22 Si(OCH3)3 (0.71 g, Compound L).

[0693] Compound L

[0694]

[0695] 11H-NMR (CDCl3, 400 MHz) δ [ppm]: 0.01 - 0.13 (m), 0.62 - 0.66 (m), 0.88 - 0.92 (m), 1.22 - 1.48 (m), 1.58 - 1.74 (m), 2.28 - 2.31 (t), 3.54 - 3.64 (m), 3.84 - 3.97 (m)

[0696] As a comparative compound, the experiment of Example 3 of International Publication No. 2016 / 199908 was additionally conducted, and the following compound (M) having the following structural formula was prepared representatively. In the formula, n is about 9.

[0697]

[0698] As a comparative compound, the following compound (N) was prepared.

[0699]

[0700] Comparative Example 3

[0701] As a comparative compound, the following compound (O) was prepared.

[0702]

[0703] Synthesis Example 8

[0704] Except for using diallylamine instead of 2,2 - diallyl - 4 - penten - 1 - amine, CH3OCO(CH2) 16 CON(CH2CH2CH2Si(OCH3)3)2 (1.21 g, compound P) was obtained according to the same formulation as in Synthesis Example 3.

[0705] Compound P

[0706]

[0707] 1H-NMR (CDCl3, 400 MHz) δ [ppm]: 1.10 - 1.40 (m, 32H), 1.63 - 1.71 (m, 6H), 2.26 (t, 2H, J = 7.2 Hz), 3.19 (t, 2H, J = 7.6 Hz), 3.27 (t, 2H, J = 7.6 Hz), 3.50 - 3.62 (m, 18H), 3.63 - 3.70 (m, 3H)

[0708] The above - obtained compounds (B), (C), (F), (G), (H) and (P) and the comparative compounds (M), (N) and (O) were diluted into 20 wt% ethanol solutions to obtain surface treatment agents 1 - 9, respectively.

[0709] <Preparation of the intermediate layer forming material containing Na>

[0710] Dissolve 2.2 g of sodium hydroxide (manufactured by Fujifilm Wako Pure Chemical Corporation) in 24 g of distilled water to obtain an 8.4 mass% aqueous sodium hydroxide solution. Mix 24 g of this 8.4 mass% aqueous sodium hydroxide solution with 20 g of MS gel (M.S.GEL D - 100 - 60A (manufactured by AGC Si-Tech Co., Ltd.)) so that the aqueous sodium hydroxide solution is absorbed into the MS gel. After drying the MS gel absorbed with the aqueous sodium hydroxide solution at 25 °C for 8 hours, it is molded using a tablet molding machine (4 MPa, 1 minute), and then fired at 1000 °C for 1 hour to obtain Formed Body 1 (pellets).

[0711] <Formation of the surface treatment layer>

[0712] Example 1

[0713] Vacuum deposit Surface Treatment Agent 1 on chemically strengthened glass (manufactured by Corning, Gorilla Glass, thickness 0.7 mm). Specifically, fill 0.1 g of Surface Treatment Agent 1 in a molybdenum boat inside the vacuum deposition apparatus, and evacuate the inside of the vacuum deposition apparatus to a pressure of 3.0×10 -3 Pa or less. Then, deposit silicon dioxide with a thickness of 7 nm by electron beam evaporation to form a silicon dioxide film, and then heat the boat by resistance heating to thereby form a surface treatment layer. After that, perform a heat treatment at 150 °C for 2 hours in an oven to obtain the surface treatment layer.

[0714] Example 2

[0715] Vacuum deposit Surface Treatment Agent 1 on chemically strengthened glass (manufactured by Corning, Gorilla Glass, thickness 0.7 mm). Specifically, fill 0.1 g of Surface Treatment Agent 1 in a molybdenum boat inside the vacuum deposition apparatus, and evacuate the inside of the vacuum deposition apparatus to a pressure of 3.0×10 -3 Pa or less. Then, use Formed Body 1 to perform deposition by electron beam evaporation to form a Na-containing silicon dioxide film with a thickness of 7 nm, and then heat the boat by resistance heating to thereby form a surface treatment layer. After that, perform a heat treatment at 150 °C for 2 hours in an oven to obtain the surface treatment layer.

[0716] Example 3

[0717] A surface treatment layer is obtained in the same manner as in Example 1 except that Surface Treatment Agent 1 is replaced with Surface Treatment Agent 2.

[0718] Example 4

[0719] A surface treatment layer was obtained in the same manner as in Example 2, except that the surface treatment agent was replaced with surface treatment agent 2.

[0720] Example 5

[0721] A surface treatment layer was obtained in the same manner as in Example 1, except that the surface treatment agent was replaced with surface treatment agent 3.

[0722] Example 6

[0723] A surface treatment layer was obtained in the same manner as in Example 1, except that the surface treatment agent was replaced with surface treatment agent 4.

[0724] Example 7

[0725] A surface treatment layer was obtained in the same manner as in Example 1, except that the surface treatment agent was replaced with surface treatment agent 5.

[0726] Example 8

[0727] A surface treatment layer was obtained in the same manner as in Example 1, except that the surface treatment agent was replaced with surface treatment agent 6.

[0728] Comparative Example 1

[0729] A surface treatment layer was obtained in the same manner as in Example 1, except that the surface treatment agent was replaced with surface treatment agent 7.

[0730] Comparative Example 2

[0731] A surface treatment agent was obtained in the same manner as in Example 1, except that the surface treatment agent was replaced with surface treatment agent 8.

[0732] Comparative Example 3

[0733] A surface treatment agent was obtained in the same manner as in Example 1, except that the surface treatment agent was replaced with surface treatment agent 9.

[0734] Evaluation of abrasion resistance

[0735] The sample article with the surface treatment layer formed was placed horizontally, and the following friction member was brought into contact with the surface of the surface treatment layer (the contact surface was a circle with a diameter of 1 cm). A load of 5 N was applied thereto, and then the friction member was reciprocated 100 times at a speed of 40 mm / second in the state where the load was applied. The static contact angle (°) of water at 5 locations was measured before and after wear, and the retention rate of the water contact angle after wear was calculated based on the average value thereof, and the evaluation was carried out as follows.

[0736] ◎ (Excellent): The retention rate of the water contact angle is greater than 86%.

[0737] ○ (Good): 70% - 85%

[0738] ×(Defect): Below 69%

[0739] ·Friction part

[0740] Use a product covered with a cotton sheet after the surface (1 cm in diameter) of the silicone rubber processed product shown below is immersed in artificial sweat with the composition shown below as the friction part.

[0741] Composition of artificial sweat:

[0742] Disodium hydrogen phosphate anhydrous: 2 g

[0743] Sodium chloride: 20 g

[0744] 85% Lactic acid: 2 g

[0745] Histidine hydrochloride: 5 g

[0746] Distilled water: 1 Kg

[0747] Silicone rubber processed product:

[0748] Process the silicone rubber stopper SR-51 produced by TIGERS POLYMER CORPORATION into a cylindrical shape with a diameter of 1 cm and a thickness of 1 cm.

[0749] Evaluation of fingerprint visibility

[0750] Add 4.0 g of glyceryl trioleate to 32 g of methoxypropanol, then add 1.6 g of the test powder No. 11 Kanto Loam specified in JIS Z8901, and stir to prepare the simulated fingerprint component. After standing for 12 hours or more, sample about 1 mL while stirring thoroughly with a magnetic stirrer, and coat it on chemically strengthened glass (produced by Corning Inc., Gorilla Glass, thickness 0.7 mm) using the spin coating method. Heat this substrate at 60 °C for 5 minutes to completely remove the unnecessary diluent methoxypropanol. Use this as the original plate for simulated fingerprint transfer. Then, press the end face (16 mm in diameter) of the small end of the No. 4 silicone rubber stopper against the above original plate with a load of 4.9 N for 10 seconds to transfer the simulated fingerprint component to the end face of the transfer material. Then, press the end face of the above transfer material against the surface of each of the above specimens with a load of 4.9 N for 10 seconds to transfer the simulated fingerprint component. Then, wipe off the simulated fingerprint attached to each specimen according to the following steps. Use BEMCOT M-3II (product name, produced by Asahi Kasei Corporation) as the wear part, with a moving speed of 60 rpm and a load of 1 kg / 3 cm 2Undergo reciprocating wear 10 times under the specified conditions. Next, based on the provisions of JIS K7136 (2000 edition), use a haze meter (manufactured by Nippon Denshoku Industries Co., Ltd., NDH7000SPII) to measure the degree of fingerprint stains after wiping. Calculate the difference in haze value from the non-attached part and evaluate it according to the following three grades.

[0751] ◎ (Excellent): Δ haze is less than 0.5%.

[0752] ○ (Good): Δ haze is 0.5% or more and less than 1%.

[0753] × (Poor): Δ haze is 1% or more.

[0754] [Table 1]

[0755] Compound Fingerprint visibility Abrasion resistance Example 1 B ◎ ◎ Example 2 B ◎ ◎ Example 3 C ◎ ◎ Example 4 C ◎ ◎ Example 5 F ◎ 〇 Example 6 G ◎ 〇 Example 7 H ◎ 〇 Example 8 P ◎ 〇 Comparative Example 1 M ◎ × Comparative Example 2 N ◎ × Comparative Example 3 O × ◎

[0756] From the above results, it can be confirmed that the compound of the present invention having a long-chain alkylene group and a functional group at the terminal has low fingerprint visibility and excellent friction durability.

[0757] Industrial applicability

[0758] The surface treatment agent of the present invention can be applied to a variety of uses.

Claims

1. A silane compound represented by the following formula (1), characterized in that: (R 1 -X 1 ) α -X 2 -(R Si ) β (1) In the formula: R 1 is R 2 -O-CO-, R 2 -COO-, R 2 -O-C(=O)-O-, R 2 -NR-CO-, R 2 -CO-NR-, R 2 -OCO-NR-, R 2 -NR 3 -COO-, R 2 -NR-CO-NR 3 -, CH2=CH-, NHR 3 -, CR 5 3-, CHR 5 2-, CH2R 5 - or a halogen atom, R 2 is a hydrogen atom, C 1-6 alkyl group or an oxyalkylene group having 1 to 30 carbon atoms, R 3 is a hydrogen atom or a C 1-6 alkyl group, R 5 is a halogen atom, X 1 is an alkylene group having 12 or more carbon atoms, X 2 is a single bond or an organic group with a valence of 2 to 10 R Si is a monovalent group containing a Si atom bonded with a hydroxyl group or a hydrolyzable group, α is an integer from 1 to 9, β is an integer from 1 to 9, The sum of α and β is equal to X 2 valence number.

2. The silane compound according to claim 1, characterized in that: R 1 is R 2 -O-CO-, R 2 -O-C(=O)-O-, R 2 -NR-CO-, R 2 -CO-NR-, R 2 -OCO-NR-, R 2 -NR 3 -COO-, R 2 -NR-CO-NR 3 -, CH2=CH-, NH2- or a bromine atom, R 2 is C 1-6 an alkyl group or a group of oxyalkylene having 1 to 30 carbon atoms, R 3 is a hydrogen atom or a C 1-6 alkyl group.

3. The silane compound according to claim 1, characterized in that: X 1 is C 12-36 alkylene.

4. The silane compound according to claim 1, characterized in that: X 1 is C 16-36 alkylene.

5. The silane compound according to claim 1, characterized in that: X 2 is a single bond, or a divalent group containing -CO-, -COO-, -OCO-, -NR 41 -, -CONR 41 -, -NR 41 CO-, -OCONR 41 -, -NR 41 -CO-NR 41 -, -O- or -S-. R 41 is a hydrogen atom or a C 1-6 alkyl group.

6. The silane compound according to claim 1, characterized in that: X 2 is a single bond or has the following formula: -X 2A -X 2B - the group shown In the formula, X 2A is -CO-, -COO-, -OCO-, -NR 41 -, -CONR 41 -, -NR 41 CO-, -OCONR 41 -, -NR 41 -CO-NR 41 -, -O- or -S-, R 41 is a hydrogen atom or a C 1-6 alkyl group X 2B is a single bond or C 1-6 alkylene group.

7. The silane compound according to claim 1, characterized in that: X 2 is a group represented by the following formula: In the formula, X a is a single bond or a divalent organic group.

8. The silane compound according to claim 1, characterized in that: R Si is a group represented by the following formula (S1), (S2), (S3), (S4) or (S5): -SiR 11 n1 R 12 3-n1 (S2) -SiR a1 k1 R b1 l1 R c1 m1 (S3) -CR d1 k2 R e1 l2 R f1 m2 (S4) -NR g1 R h1 (S5) In the formula: R 11 are each independently a hydroxyl group or a hydrolyzable group, R 12 are each independently a monovalent organic group n1 is independently an integer from 0 to 3 in each (SiR 11 n1 R 12 3-n1 ) cell, X 11 are each independently a single bond or a divalent organic group R 13 Each is independently a hydrogen atom or a monovalent organic group, t are each independently an integer of 2 or more, R 14 each independently represents a hydrogen atom, a halogen atom or -X 11 -SiR 11 n1 R 12 3-n1 , R 15 Each is independently a single bond, an oxygen atom, an alkylene group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, R a1 are each independently -Z 1 -SiR 21 p1 R 22 q1 R 23 r1 ; Z 1 are each independently a divalent organic group, R 21 each independently being -Z 1' -SiR 21' p1' R 22' q1' R 23' r1' ; R 22 each independently represents a hydroxyl group or a hydrolyzable group R 23 are each independently a monovalent organic group p1 are each independently an integer from 0 to 3, q1 are each independently an integer from 0 to 3, r1 are each independently an integer from 0 to 3, Z 1' are each independently divalent organic groups R 21' are each independently -Z 1” -SiR 22” q1” R 23” r1” ; R 22' are each independently a hydroxyl group or a hydrolyzable group, R 23' are each independently a monovalent organic group p1' are each independently an integer from 0 to 3, q1' are each independently an integer from 0 to 3, r1' are each independently an integer from 0 to 3, Z 1” are each independently divalent organic groups, R 22” are each independently a hydroxyl group or a hydrolyzable group, R 23” are each independently monovalent organic groups q1” are each independently an integer from 0 to 3, r1” are each independently an integer from 0 to 3, R b1 are each independently a hydroxyl group or a hydrolyzable group, R c1 are each independently a monovalent organic group k1 are each independently an integer from 0 to 3, l1 are each independently an integer from 0 to 3, m1 are each independently an integer from 0 to 3, wherein, there are at least 2 Si atoms bonded with a hydroxyl group or a hydrolyzable group in formula (S3), R d1 each independently being -Z 2 -CR 31 p2 R 32 q2 R 33 r2 , Z 2 are each independently a single bond, an oxygen atom or a divalent organic group, R 31 are each independently -Z 2' -CR 32' q2' R 33' r2' , R 32 are each independently -Z 3 -SiR 34 n2 R 35 3-n2 , R 33 are each independently a hydrogen atom, a hydroxyl group or a monovalent organic group, p2 are each independently an integer from 0 to 3, q2 are each independently an integer from 0 to 3, r2 are each independently an integer from 0 to 3, Z 2' are each independently a single bond, an oxygen atom or a divalent organic group, R 32' are each independently -Z 3 -SiR 34 n2 R 35 3-n2 , R 33' are each independently a hydrogen atom, a hydroxyl group or a monovalent organic group, q2' are each independently an integer from 0 to 3, r2' are each independently an integer from 0 to 3, Z 3 are each independently a single bond, an oxygen atom or a divalent organic group; R 34 are each independently a hydroxyl group or a hydrolyzable group, R 35 are each independently a monovalent organic group n2 are each independently an integer from 0 to 3, R e1 are each independently -Z 3 -SiR 34 n2 R 35 3-n2 , R f1 are each independently a hydrogen atom, a hydroxyl group or a monovalent organic group, k2 are each independently an integer from 0 to 3, l2 are each independently an integer from 0 to 3, m2 are each independently an integer from 0 to 3, wherein, there are at least 2 Si atoms bonded with a hydroxyl group or a hydrolyzable group in formula (S4), R g1 and R h1 are each independently -Z 4 -SiR 11 n1 R 12 3-n1 、-Z 4 -SiR a1 k1 R b1 l1 R c1 m1 or -Z 4 -CR d1 k2 R e1 l2 R f1 m2 , Z 4 are each independently a single bond, an oxygen atom or a divalent organic group wherein, there are at least 2 Si atoms bonded with a hydroxyl group or a hydrolyzable group in formula (S5).

9. The silane compound according to claim 1, characterized in that: R 1 is R 2 -O-CO-, CH2=CH-, NH2- or a bromine atom R 2 is methyl, X 1 is C 16-26 alkylene, X 2 is a single bond, -CO- or -CONR 41 -, R 41 is a hydrogen atom, R Si is -SiR 11 3, -CR e1 3 or -NR g1 R h1 The groups shown, wherein, in the formula -SiR 11 3, R 11 is -OR h , R h is methyl, in the formula -CR e1 3, R e1 is -Z 3 -SiR 34 3, Z 3 is C3 alkylene, R 34 is -OR h , R h is methyl, in the formula -NR g1 R h1 In, R g1 and R h1 is -Z 4 -SiR 11 3, Z 3 is C3 alkylene, R 11 is -OR h , R h is methyl.

10. The silane compound according to claim 1, characterized in that: Selected from the following compounds:

11. A surface treatment agent, characterized in that: It contains the silane compound according to claim 1.

12. The surface treatment agent according to claim 11, wherein It also contains a condensate of the silane compound according to claim 1.

13. The surface treatment agent according to claim 11, wherein , The content of the silane compound according to claim 1 and its condensate is 60% by mass or more relative to all the silane compounds contained in the surface treatment agent.

14. The surface treatment agent according to claim 11, characterized in that: It also contains a solvent selected from R 71 OR 72 、R 73 n8 C6H 6-n8 、R 74 R 75 R 76 Si-(O-SiR 77 R 78 ) m8 -R 79 、(OSiR 77 R 78 ) m9 shown compounds and C 1-10 alcohols that can be substituted, In the formula: R 71 to R 79 each independently represents a monovalent organic group having 1 to 10 carbon atoms, m8 is an integer from 1 to 6, m9 is an integer from 4 to 8, n8 is an integer from 0 to 6.

15. The surface treatment agent according to claim 11, characterized in that: It is used for vacuum evaporation coating.

16. The surface treatment agent according to claim 11, characterized in that: It is used for wet covering.

17. A pellet, characterized in that: It contains the surface treatment agent according to claim 11.

18. An article, characterized in that: It includes a substrate and a layer formed on the substrate by the silane compound according to claim 1.

19. The article according to claim 18, wherein, an intermediate layer containing silicon oxide is included between the substrate and the layer.

20. The article according to claim 19, wherein, the intermediate layer contains alkali metal atoms.

21. The article according to claim 20, wherein, at least a part of the alkali metal atoms is sodium atoms.

22. The article according to claim 18, wherein, it is an optical component.

23. The article according to claim 18, wherein, it is a display.

24. A compound represented by the following formula (2), wherein, R 1 -X 1 -R 51 (2) in the formula: R 1 is R 2 -O-CO-, R 2 -O-C(=O)-O-, R 2 -NR-CO-, R 2 -CO-NR-, R 2 -OCO-NR-, R 2 -NR 3 -COO-, R 2 -NR-CO-NR 3 -, CH2=CH-, NHR 3 -, or a halogen atom R 2 is a hydrogen atom, C 1-6 alkyl group or an oxyalkylene group having 1 to 30 carbon atoms, R 3 is a hydrogen atom or a C 1-6 alkyl group X 1 is an alkylene group having 12 or more carbon atoms, R 51 is one of the following groups: R 61 is a hydrocarbon group having 1 to 6 carbon atoms, * represents a bonding site.

Citation Information

Patent Citations

  • Surface treatment agent

    WO2016199908A1