Surface treatment agent
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- DAIKIN INDUSTRIES LTD
- Filing Date
- 2023-11-24
- Publication Date
- 2026-06-17
AI Technical Summary
Existing silane compounds provide excellent water and oil repellency but lack sufficient friction durability in surface-treated layers.
A silane compound with specific structural formulas (R 1 -R 2 -SiR 3 2 - and R 4 -R 5 -SiR 6 2 -) that form a surface treatment layer with improved friction durability, incorporating Si-C and C-C bonds to reduce ionic bonding and enhance chemical stability.
The silane compound forms a surface-treated layer with enhanced friction durability, providing improved chemical stability and reduced ionic bonding properties.
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Abstract
Description
[Technical field]
[0001] The present disclosure relates to a surface treatment agent. [Background technology]
[0002] It is known that certain silane compounds can provide excellent water and oil repellency when used in the surface treatment of a substrate (Patent Document 1). [Prior art documents] [Patent documents]
[0003] [Patent Document 1] JP 2002-97192 A Summary of the Invention [Problem to be solved by the invention]
[0004] The silane compound described in Patent Document 1 can provide a surface treatment layer with excellent water and oil repellency, but there is a demand for a compound that can provide a surface treatment layer with higher friction durability.
[0005] An object of the present disclosure is to provide a silane compound capable of forming a surface treatment layer having excellent friction durability. [Means for solving the problem]
[0006] The present disclosure includes the following aspects. [1] The following formula (1) or (2): [ka] [In formula: R S1 are each independently R 1 -R S -SiR 2 2- and R S2 -R S -SiR 2 2- and RS are each independently represented by the following formula: [ka] (In the formula: R 3 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 4 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 6are each independently 1-6 is an alkylene group, R 7 each independently represents an optionally substituted arylene group, R 8 each independently represents a single bond or C 1-6 is an alkylene group, R 9 are each independently a single bond or an oxygen atom; R 5 are each independently a hydrocarbon group; x is an integer from 0 to 200; y is an integer from 0 to 200; z is an integer from 0 to 200; y+z is greater than or equal to 1, The order of occurrence of each repeating unit enclosed in parentheses with x, y, or z is arbitrary in the formula. is a group represented by R 1 is a hydrocarbon group, R 2 are each independently a hydrocarbon group; R H each independently represents a hydroxyl group or a monovalent group containing a Si atom to which a hydrolyzable group is bonded, X A each independently represents a divalent to decavalent organic group, α is an integer from 1 to 9, β is an integer from 1 to 9, Each γ is independently an integer from 1 to 9. A silane compound represented by the formula: [2] R 2 each independently may be substituted by a halogen atom; C 1-18 is an alkyl group or an aryl group, R 5 each independently may be substituted by a halogen atom; C 1-18 is an alkyl group or an aryl group; The compound according to the above [1]. [3] R2 are each independently a methyl group or a phenyl group, R 5 are each independently a methyl group or a phenyl group; The silane compound according to the above [1] or [2]. [4] R 3 are each independently 1-12 Alkylene group or -R 6 -OR 6 The silane compound according to any one of the above [1] to [3], wherein [5] R 4 are each independently 1-12 Alkylene group or -R 6 -OR 6 The silane compound according to any one of the above [1] to [4], wherein [6] R 4 are each independently -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 The silane compound according to any one of the above [1] to [4], wherein [7] R H is represented by the following formula (S1), (S2), (S3), (S4), or (S5): [ka] [In formula: R 11 are each independently a hydroxyl group or a hydrolyzable group, R12 are each independently a monovalent organic group, n1 is (SiR 11 n1 R 12 3-n1 ) each unit independently represents an integer of 0 to 3, X 11 each independently represents a single bond or a divalent organic group, R 13 each independently represents a hydrogen atom or a monovalent organic group, Each t is independently an integer of 2 or greater; R 14 each independently represents a hydrogen atom, a halogen atom, or -X 11 -SiR 11 n1 R 12 3-n1 and R 15 each independently represents a single bond, an oxygen atom, an alkylene group having 1 to 6 carbon atoms, or an alkyleneoxy group having 1 to 6 carbon atoms, R a1 are each independently -Z 1 -SiR 21 p1 R 22 q1 R 23 r1 and; Z 1 are each independently a divalent organic group, R 21 are each independently -Z 1’ -SiR 21’ p1’ R 22’ q1’ R 23’ r1’ and; R 22 are each independently a hydroxyl group or a hydrolyzable group, R 23 are each independently a monovalent organic group, p1 is independently an integer of 0 to 3, Each q1 is independently an integer of 0 to 3, Each r1 is independently an integer of 0 to 3, Z 1’ are each independently a divalent organic group, R 21’ are each independently -Z 1” -SiR 22” q1” R 23” r1” and; R 22’ are each independently a hydroxyl group or a hydrolyzable group, R 23’ are each independently a monovalent organic group, p1' is independently an integer of 0 to 3, Each q1' is independently an integer of 0 to 3, Each r1' is independently an integer of 0 to 3, Z 1” are each independently a divalent organic group, R 22” are each independently a hydroxyl group or a hydrolyzable group, R 23” are each independently a monovalent organic group, Each q1" is independently an integer of 0 to 3, Each r1" is independently an integer of 0 to 3, R b1 are each independently a hydroxyl group or a hydrolyzable group, R c1 are each independently a monovalent organic group, Each k1 is independently an integer of 0 to 3, Each l1 is independently an integer of 0 to 3; Each m1 is independently an integer of 0 to 3, In the formula (S3), there are at least two Si atoms to which a hydroxyl group or a hydrolyzable group is bonded, R d1 are each independently -Z 2 -CR 31 p2 R 32 q2 R33 r2 and Z 2 each independently represents a single bond, an oxygen atom, or a divalent organic group, R 31 are each independently -Z 2’ -CR 32’ q2’ R 33’ r2’ and R 32 are each independently -Z 3 -SiR 34 n2 R 35 3-n2 and R 33 each independently represents a hydrogen atom, a hydroxyl group, or a monovalent organic group, p2 is independently an integer of 0 to 3, Each q2 is independently an integer of 0 to 3, Each r2 is independently an integer of 0 to 3; Z 2’ each independently represents 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 and R 33’ each independently represents a hydrogen atom, a hydroxyl group, or a monovalent organic group, Each q2' is independently an integer of 0 to 3, Each r2' is independently an integer of 0 to 3, Z 3 each independently represents 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, Each n2 is independently an integer of 0 to 3, Re1 are each independently -Z 3 -SiR 34 n2 R 35 3-n2 and R f1 each independently represents a hydrogen atom, a hydroxyl group, or a monovalent organic group, Each k2 is independently an integer of 0 to 3, Each l2 is independently an integer of 0 to 3; Each m2 is independently an integer of 0 to 3. In the formula (S4), there are at least two Si atoms having hydroxyl groups or hydrolyzable groups bonded thereto, 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 and Z 4 each independently represents a single bond, an oxygen atom, or a divalent organic group, However, in formula (S5), there are at least two Si atoms to which a hydroxyl group or a hydrolyzable group is bonded.] The silane compound according to any one of the above [1] to [6], wherein the silane compound is a group represented by the following formula: [8] R H are each independently a group represented by formula (S1), formula (S3), (S4), or (S5). [9] R H are each independently a group represented by formula (S3), (S4), or (S5).
[10] The silane compound according to any one of the above [1] to [9], wherein α, β, and γ are 1.
[11] X A is expressed by the following formula: -(R 51 ) p5 -(X 51 ) q5 - [In formula: R 51 is -(CH2) s5 - or an o-, m- or p-phenylene group, s5 is an integer from 1 to 20; X 51 is -(X 52 ) l5 - and X 52 each independently represents -O-, -S-, o-, m- or p-phenylene group, -CO-, -C(O)O-, -CONR 54 -,-O-CONR 54 -, -NR 54 - and - (CH2) n5 - is a group selected from the group consisting of R 54 are each independently a hydrogen atom or a monovalent organic group, Each n5 is independently an integer from 1 to 20, l5 is an integer from 1 to 10; p5 is 0 or 1; q5 is 0 or 1; Here, at least one of p5 and q5 is 1, and the order of the repeating units enclosed in parentheses with p5 or q5 is arbitrary. The silane compound according to any one of the above [1] to
[10] , wherein the divalent organic group is represented by the following formula:
[12] X A are each independently 1-20 Alkylene group, or -(CH2) s5 -CONH-(CH2) t5-(wherein s5 is an integer of 1 to 20, and t5 is an integer of 1 to 20).
[13] A surface treatment agent containing the silane compound according to any one of the above [1] to
[12] .
[14] A surface treatment agent comprising at least one of the siloxane-containing silane compound according to any one of the above [1] to
[12] and a compound consisting of a condensate formed by condensing at least a portion of the siloxane-containing silane compound.
[15] The surface treatment agent according to the above
[13] or
[14] , which is for vacuum deposition.
[16] The surface treatment agent according to the above
[13] or
[14] , which is for wet coating.
[17] A pellet containing the surface treatment agent according to any one of the above items
[13] to
[16] .
[18] An article comprising a substrate, and a layer formed on the substrate from the silane compound according to any one of the above items [1] to
[12] , or the surface treatment agent according to any one of the above items
[13] to
[16] .
[19] The article according to
[18] above, which is an optical component.
[20] The article according to
[19] above, which is a display.
[21] Formula (1a-3) or (2a-3): R S1 -R 61’ -Si(R 62 -CH=CH2)3(1a-3) (CH=CH2-R 62 )3Si-R 61’ -R S2 -R 61’ -Si(R 62 -CH=CH2)3(2a-3) [In the formula, R S1 are each independently R 1 -R S -SiR 2 2- and R S2 -R S -SiR 2 2- and R Sare each independently represented by the following formula: [ka] (In the formula: R 3 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 4 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 6 are each independently1-6 is an alkylene group, R 7 each independently represents an optionally substituted phenylene group or naphthylene group, R 8 each independently represents a single bond or C 1-6 is an alkylene group, R 9 are each independently a single bond or an oxygen atom; R 5 are each independently a hydrocarbon group; x is an integer from 0 to 200; y is an integer from 0 to 200; z is an integer from 0 to 200; y+z is greater than or equal to 1, The order of occurrence of each repeating unit enclosed in parentheses with x, y, or z is arbitrary in the formula. is a group represented by R 1 is a hydrocarbon group, R 2 are each independently a hydrocarbon group; R 62 is a single bond or C 1-12 is an alkylene group, R 61’ is a divalent organic group. A compound represented by the formula:
[22] Formula (1b-1) or (2b-1): R S1 -R 61 -COOR 65 (1b-1) R 65 OCO-R 61 -R S2 -R 61 -COOR 65 (2b-1) [In the formula, R S1 are each independently R 1 -R S -SiR 2 2- and R S2 -R S-SiR 2 2- and R S are each independently represented by the following formula: [ka] (In the formula: R 3 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 4 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R9 - and R 6 are each independently 1-6 is an alkylene group, R 7 each independently represents an optionally substituted phenylene group or naphthylene group, R 8 each independently represents a single bond or C 1-6 is an alkylene group, R 9 are each independently a single bond or an oxygen atom; R 5 are each independently a hydrocarbon group; x is an integer from 0 to 200; y is an integer from 0 to 200; z is an integer from 0 to 200; y+z is greater than or equal to 1, The order of occurrence of each repeating unit enclosed in parentheses with x, y, or z is arbitrary in the formula. is a group represented by R 1 is a hydrocarbon group, R 2 are each independently a hydrocarbon group; R 61 is a single bond or a divalent organic group, R 65 is a hydrogen atom or C 1-6 is an alkyl group. A compound represented by the formula:
[23] Formula (1b-2) or (2b-2): R S1 -R 61 -CONR 67 -R 66 -C(R 62 -CH=CH2)3(1b-2) (CH=CH2-R 62 )3C-R 66 -NR 67 CO-R 61 -R S2 -R 61 -CONR 67 -R66 -C(R 62 -CH=CH2)3(2b-2) [In the formula, R S1 are each independently R 1 -R S -SiR 2 2- and R S2 -R S -SiR 2 2- and R S are each independently represented by the following formula: [ka] (In the formula: R 3 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 4 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 6 are each independently 1-6 is an alkylene group, R 7 each independently represents an optionally substituted arylene group, R 8 each independently represents a single bond or C 1-6 is an alkylene group, R 9 are each independently a single bond or an oxygen atom; R 5 are each independently a hydrocarbon group; x is an integer from 0 to 200; y is an integer from 0 to 200; z is an integer from 0 to 200; y+z is greater than or equal to 1, The order of occurrence of each repeating unit enclosed in parentheses with x, y, or z is arbitrary in the formula. is a group represented by R 1 is a hydrocarbon group, R 2 are each independently a hydrocarbon group; R 61 is a single bond or C 1-12 is an alkylene group, R 62 is a single bond or C 1-12 is an alkylene group, R 66 is a single bond or C 1-12 is an alkylene group, R 67 is a hydrogen atom, C 1-18It is an alkyl group, an aryl group, or a polyether group. A compound represented by the formula:
[24] Formula (1c-2) or (2c-2): R S1 -R 61 -CON(R 62 -CH=CH2)2(1c-2) (CH=CH2-R 62 )2NCO-R 61 -R S2 -R 61 -CON(R 62 -CH=CH2)2(2c-2) [In the formula, R S1 are each independently R 1 -R S -SiR 2 2- and R S2 -R S -SiR 2 2- and R S are each independently represented by the following formula: [ka] (In the formula: R 3 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 4 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 6 are each independently 1-6 is an alkylene group, R 7 each independently represents an optionally substituted arylene group, R 8 each independently represents a single bond or C 1-6 is an alkylene group, R 9 are each independently a single bond or an oxygen atom; R 5 are each independently a hydrocarbon group; x is an integer from 0 to 200; y is an integer from 0 to 200; z is an integer from 0 to 200; y+z is greater than or equal to 1, The order of occurrence of each repeating unit enclosed in parentheses with x, y, or z is arbitrary in the formula. is a group represented by R 1 is a hydrocarbon group, R 2 are each independently a hydrocarbon group; R 61 is a single bond or C 1-12 is an alkylene group, R 62 is a single bond or C 1-12 is an alkylene group. A compound represented by the formula:
[25] Equation (1d-2) or (2d-2): R S1 -R 61 -C(OH)(R 62 -CH=CH2)2(1d-2) (CH=CH2-R 62 )2(OH)CR 61 -R S2 -R 61 -C(OH)(R 62 -CH=CH2)2(2d-2) [In the formula, R S1 are each independently R 1 -R S -SiR 2 2- and R S2 -R S -SiR 2 2- and R S are each independently represented by the following formula: [ka] (In the formula: R 3 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9-R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 4 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 6 are each independently 1-6 is an alkylene group, R 7 each independently represents an optionally substituted arylene group, R 8 each independently represents a single bond or C 1-6 is an alkylene group, R 9 are each independently a single bond or an oxygen atom; R 5 are each independently a hydrocarbon group; x is an integer from 0 to 200; y is an integer from 0 to 200; z is an integer from 0 to 200; y+z is greater than or equal to 1, The order of occurrence of each repeating unit enclosed in parentheses with x, y, or z is arbitrary in the formula. is a group represented by R 1 is a hydrocarbon group, R 2 are each independently a hydrocarbon group; R 61 is a single bond or C 1-12 is an alkylene group, R 62 is a single bond or C 1-12 is an alkylene group. A compound represented by the formula:
[26] Formula: R 74 Si(R 71 )2-R 72 -COOR 73 [In formula: R 71 each independently represents C which may be substituted by a halogen atom; 1-12 is an alkyl group, R 72 is C which may be substituted by a halogen atom 3-5 is an alkylene group, R 73 is a hydrogen atom or C which may be substituted by a halogen atom 1-3 is an alkyl group, R 74 is a halogen atom, a hydroxyl group, or a hydrolyzable group. A compound represented by the formula:
[27] R 71 is a methyl group, R 72 is a linear C 3-5 is an alkylene group, R 73 is a methyl group or an ethyl group, R 74 is a chlorine atom or a hydroxyl group; The compound according to the above
[26] . Effect of the Invention
[0007] According to the present disclosure, there is provided a silane compound capable of forming a surface treatment layer having excellent friction durability. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0008] As used herein, the term "monovalent organic group" refers to a monovalent group containing carbon. The monovalent organic group is not particularly limited, but may be a hydrocarbon group or a derivative thereof. The derivative of a hydrocarbon group refers to a group having one or more N, O, S, Si, amide, sulfonyl, siloxane, carbonyl, carbonyloxy, etc. at the end or in the molecular chain of the hydrocarbon group. In addition, when simply referring to an "organic group", it refers to a monovalent organic group. In addition, the term "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. Similarly, a trivalent or higher organic group refers to a group obtained by removing a predetermined number of hydrogen atoms from an organic group.
[0009] As used herein, the term "hydrocarbon group" refers to a group containing carbon and hydrogen, which is a group obtained by removing a hydrogen atom from a hydrocarbon. Such a hydrocarbon group includes, but is not limited to, C 1-20 Examples of the hydrocarbon group include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The "aliphatic hydrocarbon group" may be linear, branched, or cyclic, and may be saturated or unsaturated. The hydrocarbon group may contain one or more ring structures. The hydrocarbon group may be substituted with one or more substituents.
[0010] As used herein, examples of the substituent of the "hydrocarbon group" include, but are not limited to, a halogen atom, a C 1-6 Alkyl group, C 2-6 Alkenyl group, C 2-6 Alkynyl group, C 3-10 Cycloalkyl groups, C 3-10 Unsaturated cycloalkyl groups, 5-10 membered heterocyclyl groups, 5-10 membered unsaturated heterocyclyl groups, C 6-10Examples of the alkyl group include one or more groups selected from aryl groups and 5- to 10-membered heteroaryl groups.
[0011] As used herein, the term "hydrolyzable group" refers to a group that can undergo hydrolysis, i.e., a group that can be removed from the main skeleton of a compound by hydrolysis. Examples of hydrolyzable groups include -OR h , -OCOR h , -ON=CR h 2, -NR h 2, -NHR h , -NCO, halogen (wherein R h represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms), and preferably -OR h (i.e., an alkoxy group). h Examples of the alkyl group include unsubstituted alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, and isobutyl; and substituted alkyl groups such as chloromethyl. Among these, alkyl groups, particularly unsubstituted alkyl groups, are preferred, with methyl and ethyl groups being more preferred.
[0012] As used herein, the term "arylene group" refers to a divalent aromatic group. The arylene group may be a monocyclic aromatic group or a polycyclic aromatic group. The arylene group is, for example, a divalent 1-3 cyclic aromatic group, and specific examples thereof include divalent groups obtained by removing two hydrogen atoms from benzene, naphthalene, anthracene, fluorene, and phenanthrene, as shown below. The arylene group may be substituted with one or more substituents. The bonding position is arbitrary. [ka]
[0013] The compounds of the present disclosure have the following formula (1) or (2): [ka] [In formula: R S1are each independently R 1 -R S -SiR 2 2- and R S2 -R S -SiR 2 2- and R S are each independently represented by the following formula: [ka] (In the formula: R 3 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 4 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8- or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 6 are each independently 1-6 is an alkylene group, R 7 each independently represents an optionally substituted arylene group, R 8 each independently represents a single bond or C 1-6 is an alkylene group, R 9 are each independently a single bond or an oxygen atom; R 5 are each independently a hydrocarbon group; x is an integer from 0 to 200; y is an integer from 0 to 200; z is an integer from 0 to 200; y+z is greater than or equal to 1, The order of occurrence of each repeating unit enclosed in parentheses with x, y, or z is arbitrary in the formula. is a group represented by R 1 is a hydrocarbon group, R 2 are each independently a hydrocarbon group; R H each independently represents a hydroxyl group or a monovalent group containing a Si atom to which a hydrolyzable group is bonded, X A each independently represents a divalent to decavalent organic group, α is an integer from 1 to 9, β is an integer from 1 to 9, Each γ is independently an integer from 1 to 9. It is a silane compound represented by the formula:
[0014] The Si-O bond has a high ionic bond property and generally has a low chemical stability. The silane compound of the present disclosure can reduce the ionic bond property and improve the chemical stability by replacing the Si-O bond with a Si-C bond or a C-C bond.
[0015] R S are each independently represented by the following formula: [ka] [In formula: R 3 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 4 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 6 are each independently 1-6 is an alkylene group, R 7 each independently represents an optionally substituted phenylene group or naphthylene group, R 8 each independently represents a single bond or C 1-6 is an alkylene group, R 9 are each independently a single bond or an oxygen atom; R 5 are each independently a hydrocarbon group; x is an integer from 0 to 200; y is an integer from 0 to 200; z is an integer from 0 to 200; y+z is greater than or equal to 1, The order of occurrence of each repeating unit enclosed in parentheses with x, y, or z in the formula is arbitrary. It is a group represented by the following formula:
[0016] R 3 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R9 -R 7 -R 9 -R 6 -R 9 -, preferably C 1-12 Alkylene group or -R 6 -OR 6 -It is.
[0017] R 4 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 -It is.
[0018] In one embodiment, R 4 are each independently 1-12 Alkylene group or -R 6 -OR 6 -It is.
[0019] In another embodiment, R 4 are each independently -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 -It is.
[0020] In one embodiment, R 3 are each independently 1-12 Alkylene group or -R 6 -OR 6 - and R 4 are each independently 1-12 Alkylene group or -R 6 -OR 6 -It is.
[0021] In another embodiment, R 3 are each independently 1-12 Alkylene group or -R 6 -OR 6 - and R 4 are each independently -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 -It is.
[0022] Above C 1-12 The alkylene group may be linear or branched. 1-12 The alkylene group is preferably straight-chained.
[0023] Above C 1-12 The alkylene group is preferably 2-8 Alkylene group, more preferably C 2-6 It is an alkylene group.
[0024] R 6 are each independently 1-6 The above C is an alkylene group. 1-6 The alkylene group may be linear or branched. 1-6 The alkylene group is preferably straight-chained.
[0025] Above C 1-6 The alkylene group is preferably 2-4 Alkylene group, more preferably C 2-3 It is an alkylene group.
[0026] In a preferred embodiment, multiple R 6 In a group containing 6 are the same group.
[0027] R 7 each independently represents an optionally substituted arylene group.
[0028] In one embodiment, R 7 are each independently [ka] It is.
[0029] In one embodiment, R 7 is a phenylene group.
[0030] In another embodiment, R 7 is a naphthylene group.
[0031] The arylene group may have a substituent. The number of the substituents is not particularly limited and is, for example, 1 to 4, and preferably 1 or 2.
[0032] In one embodiment, the phenylene group and naphthylene group may have a substituent. The number of the substituents is not particularly limited and is, for example, 1 to 4, preferably 1 or 2. The substituted phenylene group is preferably 2,5-substituted phenylene.
[0033] The substituents on the arylene group are each independently -R 41 -R 42 It is.
[0034] R 41 is a single bond, an oxygen atom, or a sulfur atom, preferably a single bond or an oxygen atom, and more preferably an oxygen atom.
[0035] R 42 C which may be substituted by halogen 1-12 Alkyl group, -(OR 43 ) p , -R 44 -R 45 , -R 44 -OR 46 It is.
[0036] The halogen is fluorine, chlorine, bromine or iodine, preferably fluorine.
[0037] R 42 C in 1-12 The alkyl group may be straight or branched.
[0038] R 43 is C 1-6 Alkylene group, preferably C 2-4 It is an alkylene group. Such an alkylene group may be a straight chain or a branched chain.
[0039] R 44 is C 1-12 Alkylene group, preferably C 1-6 It is an alkylene group. Such an alkylene group may be a straight chain or a branched chain.
[0040] R 45 is -CH=CH2 or -OCOCH=CH2.
[0041] R 46 is a hydrogen atom or C 1-6 is an alkyl group. Such an alkyl group may be linear or branched. 1-6 The alkyl group is preferably C 1-3 Alkyl groups, more preferably C 1-2 It is preferably an alkyl group, more preferably a methyl group.
[0042] R 8 each independently represents a single bond or C 1-6 It is an alkylene group. 1-6 The alkylene group may be straight-chained or branched.
[0043] In one embodiment, R 8 is a single bond.
[0044] In another embodiment, R 8 is C 1-6 It is an alkylene group.
[0045] R 9 are each independently a single bond or an oxygen atom.
[0046] In one embodiment, R 9 is a single bond.
[0047] In another embodiment, R 9 is an oxygen atom.
[0048] R 5 are each independently a hydrocarbon group. Such a hydrocarbon group may be substituted.
[0049] R 5 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.
[0050] R 5 each independently is preferably C optionally substituted by a halogen atom 1-18 An alkyl group or an aryl group, more preferably C 1-18 It is an alkyl group or an aryl group.
[0051] Above C 1-18 The alkyl group may be straight-chain or branched-chain, but is preferably straight-chain. 1-18 The alkyl group is preferably C 1-10 Alkyl groups, more preferably C 1-6 Alkyl groups, more preferably C 1-4 It is preferably an alkyl group, and even more preferably a methyl group.
[0052] The aryl group is preferably a phenyl group.
[0053] In one embodiment, R 5 are each independently 1-6 Alkyl groups, preferably C 1-4 It is preferably an alkyl group, more preferably a methyl group.
[0054] In another embodiment, R 5 is a phenyl group.
[0055] In another embodiment, R 5 are each independently a methyl group or a phenyl group, preferably a methyl group.
[0056] x is an integer of 0 to 200, preferably an integer of 0 to 100, more preferably an integer of 1 to 100, even more preferably an integer of 5 to 50, and even more preferably an integer of 10 to 30.
[0057] In one embodiment, x is 0.
[0058] In one embodiment, x is an integer of 1 to 200, preferably an integer of 1 to 100, more preferably an integer of 5 to 50, and further preferably an integer of 10 to 30.
[0059] y is an integer from 0 to 200, preferably an integer from 0 to 100, more preferably an integer from 1 to 100, even more preferably an integer from 5 to 50, and even more preferably an integer from 10 to 30.
[0060] In one embodiment, y is 0.
[0061] In one embodiment, y is an integer of 1 to 200, preferably an integer of 1 to 100, more preferably an integer of 5 to 50, and further preferably an integer of 10 to 30.
[0062] z is an integer of 0 to 200, preferably an integer of 0 to 100, more preferably an integer of 1 to 100, further preferably an integer of 5 to 50, and further more preferably an integer of 10 to 30.
[0063] In one embodiment, z is 0.
[0064] In one embodiment, z is an integer of 1 to 200, preferably an integer of 1 to 100, more preferably an integer of 5 to 50, and further preferably an integer of 10 to 30.
[0065] R S may be a random polymer or a block polymer.
[0066] R 1 is a hydrocarbon group.
[0067] R 2 are each independently a hydrocarbon group.
[0068] R 1 and R 2 The hydrocarbon group in may be substituted.
[0069] R 1 and R2 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.
[0070] R 1 and R 2 each independently is preferably C optionally substituted by a halogen atom 1-18 An alkyl group or an aryl group, more preferably C 1-18 It is an alkyl group or an aryl group.
[0071] Above C 1-18 The alkyl group may be straight-chain or branched-chain, but is preferably straight-chain. 1-18 The alkyl group is preferably C 1-10 Alkyl groups, more preferably C 1-6 Alkyl groups, more preferably C 1-4 It is preferably an alkyl group, and even more preferably a methyl group.
[0072] The aryl group is preferably a phenyl group.
[0073] In one embodiment, R 1 and R 2 are each independently 1-6 Alkyl groups, preferably C 1-4 It is preferably an alkyl group, more preferably a methyl group.
[0074] In another embodiment, R 1 and R 2 is a phenyl group.
[0075] In another embodiment, R 1 and R 2 are each independently a methyl group or a phenyl group, preferably a methyl group.
[0076] R H are each independently a monovalent group containing a Si atom to which a hydroxyl group, a hydrolyzable group, or a monovalent organic group is bonded, and R HIt contains one or more silicon atoms having a hydroxyl group or a hydrolyzable group bonded thereto.
[0077] In a preferred embodiment, R H is represented by the following formula (S1), (S2), (S3), (S4) or (S5): [ka] [In formula: R 11 are each independently a hydroxyl group or a hydrolyzable group, R 12 are each independently a monovalent organic group, n1 is (SiR 11 n1 R 12 3-n1 ) each unit independently represents an integer of 0 to 3, X 11 each independently represents a single bond or a divalent organic group, R 13 each independently represents a hydrogen atom or a monovalent organic group, Each t is independently an integer of 2 or greater; R 14 each independently represents a hydrogen atom, a halogen atom, or -X 11 -SiR 11 n1 R 12 3-n1 and R 15 each independently represents a single bond, an oxygen atom, an alkylene group having 1 to 6 carbon atoms, or an alkyleneoxy group having 1 to 6 carbon atoms, R a1 are each independently -Z 1 -SiR 21 p1 R 22 q1 R 23 r1 and; Z 1 are each independently a divalent organic group, R 21 are each independently -Z 1’ -SiR21’ p1’ R 22’ q1’ R 23’ r1’ and; R 22 are each independently a hydroxyl group or a hydrolyzable group, R 23 are each independently a monovalent organic group, p1 is independently an integer of 0 to 3, Each q1 is independently an integer of 0 to 3, Each r1 is independently an integer of 0 to 3, Z 1’ are each independently a divalent organic group, R 21’ are each independently -Z 1” -SiR 22” q1” R 23” r1” and; R 22’ are each independently a hydroxyl group or a hydrolyzable group, R 23’ are each independently a monovalent organic group, p1' is independently an integer of 0 to 3, Each q1' is independently an integer of 0 to 3, Each r1' is independently an integer of 0 to 3, Z 1” are each independently a divalent organic group, R 22” are each independently a hydroxyl group or a hydrolyzable group, R 23” are each independently a monovalent organic group, Each q1" is independently an integer of 0 to 3, Each r1" is independently an integer of 0 to 3, R b1 are each independently a hydroxyl group or a hydrolyzable group, R c1 are each independently a monovalent organic group, Each k1 is independently an integer of 0 to 3, Each l1 is independently an integer of 0 to 3; Each m1 is independently an integer of 0 to 3, In the formula (S3), there are at least two Si atoms to which a hydroxyl group or a hydrolyzable group is bonded, R d1 are each independently -Z 2 -CR 31 p2 R 32 q2 R 33 r2 and Z 2 each independently represents a single bond, an oxygen atom, or a divalent organic group, R 31 are each independently -Z 2’ -CR 32’ q2’ R 33’ r2’ and R 32 are each independently -Z 3 -SiR 34 n2 R 35 3-n2 and R 33 each independently represents a hydrogen atom, a hydroxyl group, or a monovalent organic group, p2 is independently an integer of 0 to 3, Each q2 is independently an integer of 0 to 3, Each r2 is independently an integer of 0 to 3; Z 2’ each independently represents 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 and R 33’ each independently represents a hydrogen atom, a hydroxyl group, or a monovalent organic group, Each q2' is independently an integer of 0 to 3, Each r2' is independently an integer of 0 to 3, Z 3 each independently represents 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, Each n2 is independently an integer of 0 to 3, R e1 are each independently -Z 3 -SiR 34 n2 R 35 3-n2 and R f1 each independently represents a hydrogen atom, a hydroxyl group, or a monovalent organic group, Each k2 is independently an integer of 0 to 3, Each l2 is independently an integer of 0 to 3; Each m2 is independently an integer of 0 to 3. In the formula (S4), there are at least two Si atoms having hydroxyl groups or hydrolyzable groups bonded thereto, 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 and Z 4 each independently represents a single bond, an oxygen atom, or a divalent organic group, However, in formula (S5), there are at least two Si atoms to which a hydroxyl group or a hydrolyzable group is bonded.] It is a group represented by the following formula:
[0078] In the above formula, R 11 are each independently a hydroxyl group or a hydrolyzable group.
[0079] R 11 are preferably each independently a hydrolyzable group.
[0080] R 11 are preferably each independently -OR h , -OCOR h , -ON=CR h 2, -NR h 2, -NHR h , -NCO, or halogen (wherein R h is a substituted or unsubstituted C 1-4 alkyl group), more preferably -OR h (i.e., an alkoxy group). h Examples of R include unsubstituted alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, and isobutyl groups; and substituted alkyl groups such as chloromethyl. Among these, alkyl groups, particularly unsubstituted alkyl groups, are preferred, and methyl or ethyl groups are more preferred. In one embodiment, R h is a methyl group, and in another embodiment, R h is an ethyl group.
[0081] In the above formula, R 12 are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.
[0082] R 12 In the above, the monovalent organic group is preferably C 1-20 is an alkyl group, more preferably C 1-6 It is preferably an alkyl group, more preferably a methyl group.
[0083] In the above formula, n1 is (SiR 11 n1 R 12 3-n1 ) units are each independently an integer of 0 to 3. However, in formula (S1), n1 is 1 to 3 (SiR 11 n1 R 12 3-n1 In other words, in formula (S1), there are at least two Si atoms to which a hydroxyl group or a hydrolyzable group is bonded.
[0084] n1 is (SiR 11 n1 R 12 3-n1 ) units are each independently preferably an integer of 1 to 3, more preferably 2 or 3, and even more preferably 3.
[0085] In the above formula, X 11 are each independently a single bond or a divalent organic group. Such a divalent organic group is preferably -R 28 -O x -R 29 -(In the formula, R 28 and R 29 each independently represents a single bond or C 1-20 is an alkylene group, and x is 0 or 1. 1-20 The alkylene group may be linear or branched, but is preferably linear. 1-20 The alkylene group is preferably 1-10 Alkylene group, more preferably C 1-6 Alkylene group, more preferably C 1-3 It is an alkylene group.
[0086] In one embodiment, X 11 are each independently -C 1-6 Alkylene-OC 1-6 Alkylene- or -OC 1-6 It is alkylene.
[0087] In a preferred embodiment, X 11are each independently a single bond or a linear C 1-6 An alkylene group, preferably a single bond or a straight chain C 1-3 An alkylene group, more preferably a single bond or a straight chain C 1-2 It is preferably a linear C 1-2 It is an alkylene group.
[0088] In the above formula, R 13 are each independently a hydrogen atom or a monovalent organic group. Such a monovalent organic group is preferably 1-20 It is an alkyl group.
[0089] In a preferred embodiment, R 13 are each independently a hydrogen atom or a straight-chain C 1-6 is an alkyl group, preferably a hydrogen atom or a straight-chain C 1-3 It is an alkyl group, preferably a hydrogen atom or a methyl group.
[0090] 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 alkyleneoxy group having 1 to 6 carbon atoms.
[0091] In one embodiment, R 15 are each independently an oxygen atom, an alkylene group having 1 to 6 carbon atoms, or an alkyleneoxy group having 1 to 6 carbon atoms.
[0092] In a preferred embodiment, R 15 is a single bond.
[0093] In the above formula, each t is independently an integer of 2 or more.
[0094] In a preferred embodiment, each t is independently an integer of 2 to 10, preferably an integer of 2 to 6.
[0095] In the above formula, R 14 each independently represents a hydrogen atom, a halogen atom, or -X 11 -SiR 11n1 R 12 3-n1 The 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.
[0096] In one embodiment, formula (S1) is formula (S1-a) below. [ka] [In the formula, R 11 , R 12 , R 13 , X 11 and n1 are as defined in formula (S1) above. t1 and t2 each independently represent an integer of 1 or more, preferably an integer of 1 to 10, more preferably an integer of 2 to 10, for example, an integer of 1 to 5 or an integer of 2 to 5; The order of occurrence of each repeating unit enclosed in parentheses with t1 and t2 is arbitrary in the formula.
[0097] In a preferred embodiment, formula (S1) is formula (S1-b) below. [ka] [In the formula, R 11 , R 12 , R 13 , X 11 , n1 and t are as defined above in formula (S1).
[0098] In the above formula, R a1 are each independently -Z 1 -SiR 21 p1 R 22 q1 R 23 r1 It is.
[0099] Above Z 1 are each independently an oxygen atom or a divalent organic group.1 The structure written as is shown on the right side (SiR 21 p1 R 22 q1 R 23 r1 )
[0100] In a preferred embodiment, Z 1 is a divalent organic group.
[0101] In a preferred embodiment, Z 1 is Z 1 Preferably, in the formula (S2), (Si-Z 1 --Si) does not contain a siloxane bond.
[0102] Above Z 1 is preferably C 1-6 Alkylene group, -(CH2) z1 -O-(CH2) z2 - (wherein z1 is an integer of 0 to 6, for example, an integer of 1 to 6, and z2 is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z3 -Phenylene-(CH2) z4 - (wherein z3 is an integer of 0 to 6, for example, an integer of 1 to 6, and z4 is an integer of 0 to 6, for example, an integer of 1 to 6). 1-6 The alkylene groups may be linear or branched, but are preferably linear. These groups may contain, for example, fluorine atoms, C 1-6 Alkyl group, C 2-6 Alkenyl groups, and C 2-6 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.
[0103] In a preferred embodiment, Z 1 is C 1-6 Alkylene group or -(CH2) z3 -Phenylene-(CH2) z4 -, preferably -phenylene-(CH2) z4 -It is.
[0104] In another preferred embodiment, the Z 1 is C 1-3 In one embodiment, Z is an alkylene group. 1 can be -CH2CH2CH2-. In another embodiment, Z 1 can be -CH2CH2-.
[0105] Above R 21 are each independently -Z 1’ -SiR 21’ p1’ R 22’ q1’ R 23’ r1’ It is.
[0106] Above Z 1’ are each independently an oxygen atom or a divalent organic group. 1’ The structure written as is shown on the right side (SiR 21’ p1’ R 22’ q1’ R 23’ r1’ )
[0107] In a preferred embodiment, Z 1’ is a divalent organic group.
[0108] In a preferred embodiment, Z 1’ is Z 1’ Preferably, in the formula (S2), (Si-Z 1’ --Si) does not contain a siloxane bond.
[0109] Above Z 1’ is preferably C 1-6 Alkylene group, -(CH2) z1’ -O-(CH2) z2’ - (wherein z1' is an integer of 0 to 6, for example, an integer of 1 to 6, and z2' is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z3’ -Phenylene-(CH2) z4’- (wherein z3' is an integer of 0 to 6, for example, an integer of 1 to 6, and z4' is an integer of 0 to 6, for example, an integer of 1 to 6). 1-6 The alkylene groups may be linear or branched, but are preferably linear. These groups may contain, for example, fluorine atoms, C 1-6 Alkyl group, C 2-6 Alkenyl groups, and C 2-6 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.
[0110] In a preferred embodiment, Z 1’ is C 1-6 Alkylene group or -(CH2) z3’ -Phenylene-(CH2) z4’ -, preferably -phenylene-(CH2) z4’ -It is.
[0111] In another preferred embodiment, the Z 1’ is C 1-3 In one embodiment, Z is an alkylene group. 1’ can be -CH2CH2CH2-. In another embodiment, Z 1’ can be -CH2CH2-.
[0112] Above R 21’ are each independently -Z 1” -SiR 22” q1” R 23” r1” It is.
[0113] Above Z 1” are each independently an oxygen atom or a divalent organic group. 1” The structure written as is shown on the right side (SiR 22” q1” R 23” r1” )
[0114] In a preferred embodiment, Z 1” is a divalent organic group.
[0115] In a preferred embodiment, Z 1” is Z 1” Preferably, in the formula (S2), (Si-Z 1” --Si) does not contain a siloxane bond.
[0116] Above Z 1” is preferably C 1-6 Alkylene group, -(CH2) z1” -O-(CH2) z2” - (wherein z1" is an integer of 0 to 6, for example, an integer of 1 to 6, and z2" is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z3” -Phenylene-(CH2) z4” - (wherein z3" is an integer of 0 to 6, for example, an integer of 1 to 6, and z4" is an integer of 0 to 6, for example, an integer of 1 to 6). 1-6 The alkylene groups may be linear or branched, but are preferably linear. These groups may contain, for example, fluorine atoms, C 1-6 Alkyl group, C 2-6 Alkenyl groups, and C 2-6 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.
[0117] In a preferred embodiment, Z 1” is C 1-6 Alkylene group or -(CH2) z3” -Phenylene-(CH2) z4” -, preferably -phenylene-(CH2) z4” -It is. 1” is such a group, light resistance, particularly ultraviolet resistance, can be improved.
[0118] In another preferred embodiment, the Z 1” is C 1-3 In one embodiment, Z is an alkylene group. 1” can be -CH2CH2CH2-. In another embodiment, Z 1”can be -CH2CH2-.
[0119] Above R 22” are each independently a hydroxyl group or a hydrolyzable group.
[0120] Above R 22” are preferably each independently a hydrolyzable group.
[0121] Above R 22” are preferably each independently -OR h , -OCOR h , -ON=CR h 2, -NR h 2, -NHR h , -NCO, or halogen (wherein R h is a substituted or unsubstituted C 1-4 alkyl group), more preferably -OR h (i.e., an alkoxy group). h Examples of R include unsubstituted alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, and isobutyl groups; and substituted alkyl groups such as chloromethyl. Among these, alkyl groups, particularly unsubstituted alkyl groups, are preferred, and methyl or ethyl groups are more preferred. In one embodiment, R h is a methyl group, and in another embodiment, R h is an ethyl group.
[0122] Above R 23” are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.
[0123] Above R 23” In the above, the monovalent organic group is preferably C 1-20 is an alkyl group, more preferably C 1-6 It is preferably an alkyl group, more preferably a methyl group.
[0124] Each of the q1″ independently represents an integer of 0 to 3, and each of the r1″ independently represents an integer of 0 to 3. The sum of q1″ and r1″ is (SiR 22” q1” R 23” r1” ) units, it is 3.
[0125] The above q1" is (SiR 22” q1” R 23” r1” ) units are each independently preferably an integer of 1 to 3, more preferably 2 or 3, and even more preferably 3.
[0126] Above R 22’ are each independently a hydroxyl group or a hydrolyzable group.
[0127] R 22’ are preferably each independently a hydrolyzable group.
[0128] R 22’ are preferably each independently -OR h , -OCOR h , -ON=CR h 2, -NR h 2, -NHR h , -NCO, or halogen (wherein R h is a substituted or unsubstituted C 1-4 alkyl group), more preferably -OR h (i.e., an alkoxy group). h Examples of R include unsubstituted alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, and isobutyl groups; and substituted alkyl groups such as chloromethyl. Among these, alkyl groups, particularly unsubstituted alkyl groups, are preferred, and methyl or ethyl groups are more preferred. In one embodiment, R h is a methyl group, and in another embodiment, R h is an ethyl group.
[0129] Above R 23’are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.
[0130] R 23’ In the above, the monovalent organic group is preferably C 1-20 is an alkyl group, more preferably C 1-6 It is preferably an alkyl group, more preferably a methyl group.
[0131] Each of the p1's is independently an integer of 0 to 3, each of the q1's is independently an integer of 0 to 3, and each of the r1's is independently an integer of 0 to 3. The sum of p', q1', and r1' is (SiR 21’ p1’ R 22’ q1’ R 23’ r1’ ) units, it is 3.
[0132] In one embodiment, p1' is 0.
[0133] In one embodiment, p1' is (SiR 21’ p1’ R 22’ q1’ R 23’ r1’ ) units may each independently be an integer of 1 to 3, an integer of 2 to 3, or 3. In a preferred embodiment, p1' is 3.
[0134] In one embodiment, q1' is (SiR 21’ p1’ R 22’ q1’ R 23’ r1’ ) units each independently represents an integer of 1 to 3, preferably an integer of 2 or 3, and more preferably 3.
[0135] In one embodiment, p1' is 0 and q1' is (SiR 21’ p1’ R 22’ q1’ R 23’r1’ ) units each independently represents an integer of 1 to 3, preferably an integer of 2 or 3, and more preferably 3.
[0136] Above R 22 are each independently a hydroxyl group or a hydrolyzable group.
[0137] R 22 are preferably each independently a hydrolyzable group.
[0138] R 22 are preferably each independently -OR h , -OCOR h , -ON=CR h 2, -NR h 2, -NHR h , -NCO, or halogen (wherein R h is a substituted or unsubstituted C 1-4 alkyl group), more preferably -OR h (i.e., an alkoxy group). h Examples of R include unsubstituted alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, and isobutyl groups; and substituted alkyl groups such as chloromethyl. Among these, alkyl groups, particularly unsubstituted alkyl groups, are preferred, and methyl or ethyl groups are more preferred. In one embodiment, R h is a methyl group, and in another embodiment, R h is an ethyl group.
[0139] Above R 23 are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.
[0140] R 23 In the above, the monovalent organic group is preferably C 1-20 is an alkyl group, more preferably C 1-6 It is preferably an alkyl group, more preferably a methyl group.
[0141] Each of the above p1's is independently an integer of 0 to 3, each of the q1's is independently an integer of 0 to 3, and each of the r1's is independently an integer of 0 to 3. The sum of p1, q1, and r1 is (SiR 21 p1 R 22 q1 R 23 r1 ) units, it is 3.
[0142] In one embodiment, p1 is 0.
[0143] In one embodiment, p1 is (SiR 21 p1 R 22 q1 R 23 r1 ) units may each independently be an integer of 1 to 3, an integer of 2 to 3, or 3. In a preferred embodiment, p1 is 3.
[0144] In one embodiment, q1 is (SiR 21 p1 R 22 q1 R 23 r1 ) units each independently represents an integer of 1 to 3, preferably an integer of 2 or 3, and more preferably 3.
[0145] In one embodiment, p1 is 0 and q1 is (SiR 21 p1 R 22 q1 R 23 r1 ) units each independently represents an integer of 1 to 3, preferably an integer of 2 or 3, and more preferably 3.
[0146] In the above formula, R b1 are each independently a hydroxyl group or a hydrolyzable group.
[0147] Above R b1 are preferably each independently a hydrolyzable group.
[0148] Above R b1 are preferably each independently -OR h , -OCOR h , -ON=CR h 2, -NR h 2, -NHR h , -NCO, or halogen (wherein R h is a substituted or unsubstituted C 1-4 alkyl group), more preferably -OR h (i.e., an alkoxy group). h Examples of R include unsubstituted alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, and isobutyl groups; and substituted alkyl groups such as chloromethyl. Among these, alkyl groups, particularly unsubstituted alkyl groups, are preferred, and methyl or ethyl groups are more preferred. In one embodiment, R h is a methyl group, and in another embodiment, R h is an ethyl group.
[0149] In the above formula, R c1 are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.
[0150] Above R c1 In the above, the monovalent organic group is preferably C 1-20 is an alkyl group, more preferably C 1-6 It is preferably an alkyl group, more preferably a methyl group.
[0151] Each of the k1's is independently an integer of 0 to 3, each of the l1's is independently an integer of 0 to 3, and each of the m1's is independently an integer of 0 to 3. The sum of k1, l1 and m1 is (SiR a1 k1 R b1 l1 R c1 m1 ) units, it is 3.
[0152] In one embodiment, k1 is (SiRa1 k1 R b1 l1 R c1 m1 ) units are each independently an integer of 1 to 3, preferably 2 or 3, and more preferably 3. In a preferred embodiment, k1 is 3.
[0153] In formula (S2), there are at least two Si atoms having hydroxyl groups or hydrolyzable groups bonded thereto.
[0154] In a preferred embodiment, in the terminal portion of formula (S2), there are at least two Si atoms to which hydroxyl groups or hydrolyzable groups are bonded.
[0155] In a preferred embodiment, the group represented by formula (S2) is -Z 1 -SiR 22 q1 R 23 r1 (wherein q1 is an integer of 1 to 3, preferably 2 or 3, more preferably 3, and r1 is an integer of 0 to 2); -Z 1’ -SiR 22’ q1’ R 23’ r1’ (In the formula, q1' is an integer of 1 to 3, preferably 2 or 3, more preferably 3, and r1' is an integer of 0 to 2), or -Z 1” -SiR 22” q1” R 23” r1” (wherein q1″ is an integer of 1 to 3, preferably 2 or 3, more preferably 3, and r1″ is an integer of 0 to 2). Z 1 , Z 1’ , Z 1” , R 22 , R 23 , R 22’ , R 23’ , R 22” , and R 23” has the same meaning as above.
[0156] In a preferred embodiment, in formula (S2), R21’ When present, at least one, and preferably all, R 21’ In the above formula, q1″ is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.
[0157] In a preferred embodiment, in formula (S2), R 21 When present, at least one, and preferably all, R 21 In the above formula, p1' is 0, and q1' is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.
[0158] In a preferred embodiment, in formula (S2), R a1 When present, at least one, and preferably all, R a1 In the above formula, p1 is 0, and q1 is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.
[0159] In a preferred embodiment, in formula (S2), k1 is 2 or 3, preferably 3; p1 is 0; and q1 is 2 or 3, preferably 3.
[0160] R d1 are each independently -Z 2 -CR 31 p2 R 32 q2 R 33 r2 It is.
[0161] Z 2 are each independently a single bond, an oxygen atom, or a divalent organic group. 2 The structure written as is shown on the right side (CR 31 p2 R 32 q2 R 33 r2 )
[0162] In a preferred embodiment, Z 2 is a divalent organic group.
[0163] In a preferred embodiment, Z 2 does not contain a siloxane bond.
[0164] Above Z 2 is preferably C 1-6 Alkylene group, -(CH2) z5 -O-(CH2) z6 - (wherein z5 is an integer of 0 to 6, for example, an integer of 1 to 6, and z6 is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z7 -Phenylene-(CH2) z8 - (wherein z7 is an integer of 0 to 6, for example, an integer of 1 to 6, and z8 is an integer of 0 to 6, for example, an integer of 1 to 6). 1-6 The alkylene groups may be linear or branched, but are preferably linear. These groups may contain, for example, fluorine atoms, C 1-6 Alkyl group, C 2-6 Alkenyl groups, and C 2-6 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.
[0165] In a preferred embodiment, Z 2 is C 1-6 Alkylene group or -(CH2) z7 -Phenylene-(CH2) z8 -, preferably -phenylene-(CH2) z8 -It is. 2 is such a group, light resistance, particularly ultraviolet resistance, can be improved.
[0166] In another preferred embodiment, the Z 2 is C 1-3 In one embodiment, Z is an alkylene group. 2 can be -CH2CH2CH2-. In another embodiment, Z 2 can be -CH2CH2-.
[0167] R 31 are each independently -Z 2’ -CR 32’q2’ R 33’ r2’ It is.
[0168] Z 2’ are each independently a single bond, an oxygen atom, or a divalent organic group. 2’ The structure written as is shown on the right side (CR 32’ q2’ R 33’ r2’ )
[0169] In a preferred embodiment, Z 2’ does not contain a siloxane bond.
[0170] Above Z 2’ is preferably C 1-6 Alkylene group, -(CH2) z5’ -O-(CH2) z6’ - (wherein z5' is an integer of 0 to 6, for example, an integer of 1 to 6, and z6' is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z7’ -Phenylene-(CH2) z8’ - (wherein z7' is an integer of 0 to 6, for example, an integer of 1 to 6, and z8' is an integer of 0 to 6, for example, an integer of 1 to 6). 1-6 The alkylene groups may be linear or branched, but are preferably linear. These groups may contain, for example, fluorine atoms, C 1-6 Alkyl group, C 2-6 Alkenyl groups, and C 2-6 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.
[0171] In a preferred embodiment, Z 2’ is C 1-6 Alkylene group or -(CH2) z7’ -Phenylene-(CH2) z8’ -, preferably -phenylene-(CH2) z8’ -It is. 2’ is such a group, light resistance, particularly ultraviolet resistance, can be improved.
[0172] In another preferred embodiment, the Z 2’ is C 1-3 In one embodiment, Z is an alkylene group. 2’ can be -CH2CH2CH2-. In another embodiment, Z 2’ can be -CH2CH2-.
[0173] Above R 32’ are each independently -Z 3 -SiR 34 n2 R 35 3-n2 It is.
[0174] Above Z 3 are each independently a single bond, an oxygen atom, or a divalent organic group. 3 The structure written as is shown on the right side (SiR 34 n2 R 35 3-n2 )
[0175] In one embodiment, Z 3 is an oxygen atom.
[0176] In one embodiment, Z 3 is a divalent organic group.
[0177] In a preferred embodiment, Z 3 does not contain a siloxane bond.
[0178] Above Z 3 is preferably C 1-6 Alkylene group, -(CH2) z5” -O-(CH2) z6” - (wherein z5" is an integer of 0 to 6, for example, an integer of 1 to 6, and z6" is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z7” -Phenylene-(CH2) z8” - (wherein z7" is an integer of 0 to 6, for example, an integer of 1 to 6, and z8" is an integer of 0 to 6, for example, an integer of 1 to 6).1-6 The alkylene groups may be linear or branched, but are preferably linear. These groups may contain, for example, fluorine atoms, C 1-6 Alkyl group, C 2-6 Alkenyl groups, and C 2-6 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.
[0179] In a preferred embodiment, Z 3 is C 1-6 Alkylene group or -(CH2) z7” -Phenylene-(CH2) z8” -, preferably -phenylene-(CH2) z8” -It is. 3 is such a group, light resistance, particularly ultraviolet resistance, can be improved.
[0180] In another preferred embodiment, the Z 3 is C 1-3 In one embodiment, Z is an alkylene group. 3 can be -CH2CH2CH2-. In another embodiment, Z 3 can be -CH2CH2-.
[0181] Above R 34 are each independently a hydroxyl group or a hydrolyzable group.
[0182] R 34 are preferably each independently a hydrolyzable group.
[0183] R 34 are preferably each independently -OR h , -OCOR h , -ON=CR h 2, -NR h 2, -NHR h , -NCO, or halogen (wherein R h is a substituted or unsubstituted C 1-4 alkyl group), more preferably -OR h (i.e., an alkoxy group).h Examples of R include unsubstituted alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, and isobutyl groups; and substituted alkyl groups such as chloromethyl. Among these, alkyl groups, particularly unsubstituted alkyl groups, are preferred, and methyl or ethyl groups are more preferred. In one embodiment, R h is a methyl group, and in another embodiment, R h is an ethyl group.
[0184] Above R 35 are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.
[0185] Above R 35 In the above, the monovalent organic group is preferably C 1-20 is an alkyl group, more preferably C 1-6 It is preferably an alkyl group, more preferably a methyl group.
[0186] In the above formula, n2 is (SiR 34 n2 R 35 3-n2 ) units are each independently an integer of 0 to 3. However, in the terminal portion of formula (S3), n2 is 1 to 3 (SiR 34 n2 R 35 3-n2 In other words, at least two Si atoms having hydroxyl groups or hydrolyzable groups bonded thereto are present in the terminal portion of formula (S3).
[0187] n2 is (SiR 34 n2 R 35 3-n2 ) units are each independently preferably an integer of 1 to 3, more preferably 2 or 3, and even more preferably 3.
[0188] Above R 33’are each independently a hydrogen atom, a hydroxyl group, or a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.
[0189] Above R 33’ In the above, the monovalent organic group is preferably C 1-20 Alkyl group or -(C s H 2s ) t1 -(OC s H 2s ) t2 (wherein s is an integer of 1 to 6, preferably an integer of 2 to 4; t1 is 1 or 0, preferably 0; and t2 is an integer of 1 to 20, preferably an integer of 2 to 10, more preferably an integer of 2 to 6), more preferably C 1-20 Alkyl groups, more preferably C 1-6 An alkyl group, particularly preferably a methyl group, is preferred.
[0190] In one embodiment, R 33’ is a hydroxyl group.
[0191] In another embodiment, R 33’ is a monovalent organic group, preferably C 1-20 is an alkyl group, more preferably C 1-6 It is an alkyl group.
[0192] Each of the q2's is independently an integer of 0 to 3, and each of the r2's is independently an integer of 0 to 3. The sum of q2' and r2' is not more than (CR 32’ q2’ R 33’ r2’ ) units, it is 3.
[0193] q2' is (CR 32’ q2’ R 33’ r2’ ) units are each independently preferably an integer of 1 to 3, more preferably 2 or 3, and even more preferably 3.
[0194] R 32are each independently -Z 3 -SiR 34 n2 R 35 3-n2 This is -Z 3 -SiR 34 n2 R 35 3-n2 is the above R 32’ This has the same meaning as described above.
[0195] Above R 33 are each independently a hydrogen atom, a hydroxyl group, or a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.
[0196] Above R 33 In the above, the monovalent organic group is preferably C 1-20 Alkyl group or -(C s H 2s ) t1 -(OC s H 2s ) t2 (wherein s is an integer of 1 to 6, preferably an integer of 2 to 4; t1 is 1 or 0, preferably 0; and t2 is an integer of 1 to 20, preferably an integer of 2 to 10, more preferably an integer of 2 to 6), more preferably C 1-20 Alkyl groups, more preferably C 1-6 An alkyl group, particularly preferably a methyl group, is preferred.
[0197] In one embodiment, R 33 is a hydroxyl group.
[0198] In another embodiment, R 33 is a monovalent organic group, preferably C 1-20 is an alkyl group, more preferably C 1-6 It is an alkyl group.
[0199] The above p2's are each independently an integer of 0 to 3, q2's are each independently an integer of 0 to 3, and r2's are each independently an integer of 0 to 3. The sum of p2, q2, and r2 is (CR 31p2 R 32 q2 R 33 r2 ) units, it is 3.
[0200] In one embodiment, p2 is 0.
[0201] In one embodiment, p2 is (CR 31 p2 R 32 q2 R 33 r2 ) units may each independently be an integer of 1 to 3, an integer of 2 to 3, or 3. In a preferred embodiment, p2 is 3.
[0202] In one embodiment, q2 is (CR 31 p2 R 32 q2 R 33 r2 ) units each independently represents an integer of 1 to 3, preferably an integer of 2 or 3, and more preferably 3.
[0203] In one embodiment, p2 is 0 and q2 is (CR 31 p2 R 32 q2 R 33 r2 ) units each independently represents an integer of 1 to 3, preferably an integer of 2 or 3, and more preferably 3.
[0204] Above R e1 are each independently -Z 3 -SiR 34 n2 R 35 3-n2 This is -Z 3 -SiR 34 n2 R 35 3-n2 is the above R 32’ This has the same meaning as described above.
[0205] Above Rf1 are each independently a hydrogen atom, a hydroxyl group, or a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.
[0206] Above R f1 In the above, the monovalent organic group is preferably C 1-20 Alkyl group or -(C s H 2s ) t1 -(OC s H 2s ) t2 (wherein s is an integer of 1 to 6, preferably an integer of 2 to 4; t1 is 1 or 0, preferably 0; and t2 is an integer of 1 to 20, preferably an integer of 2 to 10, more preferably an integer of 2 to 6), more preferably C 1-20 Alkyl groups, more preferably C 1-6 An alkyl group, particularly preferably a methyl group, is preferred.
[0207] In one embodiment, R f1 is a hydroxyl group.
[0208] In another embodiment, R f1 is a monovalent organic group, preferably C 1-20 is an alkyl group, more preferably C 1-6 It is an alkyl group.
[0209] The above k2's are each independently an integer of 0 to 3, the l2's are each independently an integer of 0 to 3, and the m2's are each independently an integer of 0 to 3. The sum of k2, l2, and m2 is (CR d1 k2 R e1 l2 R f1 m2 ) units, it is 3.
[0210] In one embodiment, n2 is 1 to 3, preferably 2 or 3, more preferably 3 (SiR 34 n2 R 35 3-n2) units are present at each terminal portion of formula (S3) by 2 or more, for example, 2 to 27, preferably 2 to 9, more preferably 2 to 6, further preferably 2 to 3, and particularly preferably 3.
[0211] In a preferred embodiment, in formula (S3), R 32’ When present, at least one, and preferably all, R 32’ In the above formula, n2 is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.
[0212] In a preferred embodiment, in formula (S3), R 32 When present, at least one, and preferably all, R 32 In the above formula, n2 is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.
[0213] In a preferred embodiment, in formula (S3), R e1 When present, at least one, and preferably all, R a1 In the above formula, n2 is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.
[0214] In a preferred embodiment, in formula (S3), k2 is 0, l2 is 2 or 3, preferably 3, and n2 is 2 or 3, preferably 3.
[0215] Above 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 f1m2 Here, 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 as defined above.
[0216] In a preferred embodiment, R g1 and R h1 are each independently -Z 4 -SiR 11 n1 R 12 3-n1 It is.
[0217] Above Z 4 are each independently a single bond, an oxygen atom, or a divalent organic group. 4 The structure written as is shown on the right side (SiR 11 n1 R 12 3-n1 )
[0218] In one embodiment, Z 4 is an oxygen atom.
[0219] In one embodiment, Z 4 is a divalent organic group.
[0220] In a preferred embodiment, Z 4 does not contain a siloxane bond.
[0221] Above Z 4 is preferably C 1-6 Alkylene group, -(CH2) z5” -O-(CH2) z6” - (wherein z5" is an integer of 0 to 6, for example, an integer of 1 to 6, and z6" is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z7” -Phenylene-(CH2) z8”- (wherein z7" is an integer of 0 to 6, for example, an integer of 1 to 6, and z8" is an integer of 0 to 6, for example, an integer of 1 to 6). 1-6 The alkylene groups may be linear or branched, but are preferably linear. These groups may contain, for example, fluorine atoms, C 1-6 Alkyl group, C 2-6 Alkenyl groups, and C 2-6 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.
[0222] In a preferred embodiment, Z 4 is C 1-6 Alkylene group or -(CH2) z7” -Phenylene-(CH2) z8” -, preferably -phenylene-(CH2) z8” -It is. 3 is such a group, light resistance, particularly ultraviolet resistance, can be improved.
[0223] In another preferred embodiment, the Z 4 is C 1-3 In one embodiment, Z is an alkylene group. 4 can be -CH2CH2CH2-. In another embodiment, Z 4 can be -CH2CH2-.
[0224] In one embodiment, formulas (S1), (S2), (S3), (S4) and (S5) do not contain a siloxane bond.
[0225] In one embodiment, R H is a group represented by formula (S1), (S3), (S4) or (S5).
[0226] In one embodiment, R H is a group represented by formula (S3), (S4) or (S5).
[0227] In one embodiment, R H is a group represented by formula (S3) or (S4).
[0228] In one embodiment, R H is a group represented by formula (S5).
[0229] In one embodiment, R H 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, 13 is a hydrogen atom, and X 11 is a single bond or -R 28 -O x -R 29 -(In the formula, R 28 and R 29 each independently represents a single bond or C 1-20 an alkylene group, and x is 0 or 1; and n1 is 1 to 3, preferably 2 to 3, and more preferably 3.
[0230] In one embodiment, R H is a group represented by the formula (S2). In a preferred embodiment, n1 is 1 to 3, preferably 2 to 3, and more preferably 3.
[0231] In one embodiment, R H is a group represented by formula (S3). In a preferred embodiment, formula (S3) is -SiR a1 2R c1 , or -SiR a1 3, R a1 -Z 1 -SiR 22 q1 R 23 r1 and Z 1 is C 1-6 Alkylene group, -(CH2) z1 -O-(CH2) z2 - (wherein z1 is an integer of 0 to 6, for example, an integer of 1 to 6, and z2 is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z3 -Phenylene-(CH2) z4- (wherein z3 is an integer of 0 to 6, for example, an integer of 1 to 6, and z4 is an integer of 0 to 6, for example, an integer of 1 to 6), preferably C 1-6 It is an alkylene group, and q1 is 1 to 3, preferably 2 to 3, and more preferably 3.
[0232] In one embodiment, R H is a group represented by formula (S4). In a preferred embodiment, formula (S4) is -CR e1 2R f1 , or -CR e1 3, R e1 -Z 3 -SiR 34 n2 R 35 3-n2 and Z 3 is C 1-6 Alkylene group, -(CH2) z5” -O-(CH2) z6” - (wherein z5" is an integer of 0 to 6, for example, an integer of 1 to 6, and z6" is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z7” -Phenylene-(CH2) z8” - (wherein z7" is an integer of 0 to 6, for example, an integer of 1 to 6, and z8" is an integer of 0 to 6, for example, an integer of 1 to 6), preferably C 1-6 It is an alkylene group, and n2 is 1 to 3, preferably 2 to 3, and more preferably 3.
[0233] In one embodiment, R H is a group represented by formula (S5). In a preferred embodiment, R g1 and R h1 -Z 4 -SiR 11 n1 R 12 3-n1 and Z 4 is C 1-6 Alkylene group, -(CH2) z5” -O-(CH2) z6” - (wherein z5" is an integer of 0 to 6, for example, an integer of 1 to 6, and z6" is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z7”-Phenylene-(CH2) z8” - (wherein z7" is an integer of 0 to 6, for example, an integer of 1 to 6, and z8" is an integer of 0 to 6, for example, an integer of 1 to 6), preferably C 1-6 It is an alkylene group, and n1 is 1 to 3, preferably 2 to 3, and more preferably 3.
[0234] X A The silalkylene moiety (R S1 or R S2 ) and the silane moiety (R H ) is interpreted as a linker connecting the X A may be any group as long as the compounds represented by formulas (1) and (2) can exist stably.
[0235] In formula (1), α is an integer from 1 to 9, and β is an integer from 1 to 9. These α and β are X A The sum of α and β can vary depending on the valence of X A For example, X A When X is a decavalent organic group, the sum of α and β is 10, and for example, α can be 9 and β can be 1, α can be 5 and β can be 5, or α can be 1 and β can be 9. A When is a divalent organic group, α and β are 1.
[0236] In formula (2), γ is an integer from 1 to 9. γ is X A That is, γ can vary depending on the valence of X A is the valence of 1 minus 0.
[0237] X A each independently represents a single bond or a divalent to decavalent organic group.
[0238] X AThe divalent to decavalent organic group in is preferably a divalent to octavalent organic group. In one embodiment, the divalent to decavalent organic group is preferably a divalent to tetravalent organic group, more preferably a divalent organic group. In another embodiment, the divalent to decavalent organic group is preferably a trivalent to octavalent organic group, more preferably a trivalent to hexavalent organic group.
[0239] In one embodiment, X A is a single bond or a divalent organic group, and α, β, and γ are 1.
[0240] In one embodiment, X A is a trivalent to hexavalent organic group, α is 1, β is 2 to 5, and γ is 2 to 5.
[0241] In one embodiment, X A is a trivalent organic group, α is 1, and β is 2.
[0242] X A When is a single bond or a divalent organic group, formulas (1) and (2) are represented by the following formulas (1') and (2'). [ka]
[0243] In one embodiment, X A is a divalent organic group.
[0244] In one embodiment, X A Examples of the formula include the following formula: -(R 51 ) p5 -(X 51 ) q5 - [In formula: R 51 is a single bond, -(CH2) s5 - or an o-, m- or p-phenylene group, preferably -(CH2) s5 - and s5 is an integer of 1 to 20, preferably an integer of 1 to 15, more preferably an integer of 1 to 10, even more preferably an integer of 1 to 6, for example, an integer of 1 to 3, or an integer of 1 to 20, preferably an integer of 4 to 15, more preferably an integer of 7 to 13; X 51 is -(X 52 ) l5 - and X 52 each independently represents -O-, -S-, o-, m- or p-phenylene group, -CO-, -C(O)O-, -CONR 54 -,-O-CONR 54 -, -NR 54 - and - (CH2) n5 - is a group selected from the group consisting of R 54 are each independently a hydrogen atom or a monovalent organic group, and are preferably a hydrogen atom, a phenyl group, or C 1-6 an alkyl group (preferably a methyl group) or an oxyalkylene-containing group having 1 to 10 carbon atoms, n5 each independently represents an integer of 1 to 20, preferably an integer of 1 to 15, more preferably an integer of 1 to 10, further more preferably an integer of 1 to 6, for example, an integer of 1 to 3; l5 is an integer from 1 to 10, preferably an integer from 1 to 5, and more preferably an integer from 1 to 3; p5 is 0 or 1; q5 is 0 or 1; wherein at least one of p5 and q5 is 1, and the order of the repeating units enclosed in parentheses with p5 or q5 is arbitrary. Here, X is a divalent organic group represented by the formula: A (Typically X A Hydrogen atoms of C 1-3 Alkyl group and C 1-3 In a preferred embodiment, X A is not substituted with these groups.
[0245] The oxyalkylene-containing group having 1 to 10 carbon atoms is -OC 1-10 alkylene-containing groups, such as -R 55 -(-OC 1-10 Alkylene) n -R 56 (In the formula, R 55 is a single bond or a divalent organic group, preferably C 1-6 is an alkylene group, n is an integer of any value, preferably an integer of 2 to 10, R 56 is a hydrogen atom or a monovalent organic group, preferably C 1-6 The alkylene group may be a straight chain or a branched chain.
[0246] In a preferred embodiment, X A are each independently -(R 51 ) p5 -(X 51 ) q5 -R 52 -It is. 52 is a single bond, -(CH2) t5 - or an o-, m- or p-phenylene group, preferably -(CH2) t5 t5 is an integer of 1 to 20, preferably an integer of 2 to 6, and more preferably an integer of 2 to 3. 52 (Typically R 52 Hydrogen atoms of C 1-3 Alkyl group and C 1-3 In a preferred embodiment, R 56 is not substituted with these groups.
[0247] Preferably, X A are each independently C 1-20 An alkylene group, -R 51 -X 53 -R 52 -or [In the formula, R 51 and R 52 has the same meaning as above, X53 teeth, -O-, -S-, -CO-, -C(O)O-, -CONR 54 -, -O-CONR 54 -, -O-(CH2) u5 -CONR 54 -, -O-(CH2) u5 -CO-, or -CONR 54 -(CH2) u5 -N(R 54 )-, (In the formula, R 54 has the same meaning as above, and u5 is an integer of 1 to 20, preferably an integer of 2 to 6, and more preferably an integer of 2 to 3. It could be.
[0248] More preferably, X A are each independently C 1-20 An alkylene group, -(CH2) s5 -X 53 -, -X 53 -(CH2) t5 -or -(CH2) s5 -X 53 -(CH2) t5 - [where, X 53 , s5 and t5 are as defined above.] It is.
[0249] In a preferred embodiment, X A are each independently C 1-20 An alkylene group, -(CH2) s5 -X 53 -, -X 53 -(CH2) t5 -or -(CH2) s5 -X 53 -(CH2) t5 - [In the formula, X 53 -O-, -CO-, -CONR 54 -,-O-CONR 54 -, -O-(CH2) u5 -CONR 54 - or -O-(CH2) u5 -CO-, R 54 are each independently a hydrogen atom, a phenyl group, or C 1-6 an alkyl group (preferably a methyl group) or an oxyalkylene-containing group having 1 to 10 carbon atoms, s5, t5, and u5 are as defined above.] It could be.
[0250] In a preferred embodiment, X A are each independently -(CH2) s5 -O-(CH2) t5 -, -(CH2) s5 -CONR 54 -(CH2) t5 -, -(CH2) s5 -O-(CH2) u5 -CO-, or -(CH2) s5 -O-(CH2) u5 -CONR 54 -(CH2) t5 - [In the formula, R 54 are each independently a hydrogen atom, a phenyl group, or C 1-6 an alkyl group (preferably a methyl group) or an oxyalkylene-containing group having 1 to 10 carbon atoms, s5, t5, and u5 are as defined above.] It could be.
[0251] In a preferred embodiment, X A is C 1-20Alkylene group, or -(CH2) s5 -CONH-(CH2) t5 -It is.
[0252] In one embodiment, X A is C 1-20 It is an alkylene group.
[0253] In another embodiment, X A is -(CH2) s5 -CONH-(CH2) t5 -It is.
[0254] X A are each independently a fluorine atom, C 1-3 Alkyl group and C 1-3 Fluoroalkyl groups (preferably C 1-3 perfluoroalkyl groups). A is non-substituted.
[0255] Furthermore, the above X A The left side of each equation is R S1 or R S2 and the right side is R H Bind to.
[0256] In one embodiment, the silane compound of the present disclosure is a silane compound represented by formula (1).
[0257] In one embodiment, the silane compound of the present disclosure is a silane compound represented by formula (2).
[0258] The silane compound represented by the above formula (1) or (2) is not particularly limited, but may be 5×10 2 ~1×10 5 From the viewpoint of wear resistance, the silane compound represented by the above formula (1) or (2) preferably has a number average molecular weight of 1,000 to 30,000, more preferably 1,500 to 10,000. The "number average molecular weight" is defined as 1The value is measured by H-NMR.
[0259] The silane compound can be obtained, for example, by reacting a compound having a silalkylene structure with a compound having a hydrolyzable silane group.
[0260] Polysilalkylenes are known to be synthesized, for example, by a method involving ring-opening polymerization of silacyclobutane (JP 2015-54945 A).
[0261] The monomer used in the synthesis can be silacycloalkane (cyclic silalkylene). For example, 1,1-dimethylsilacyclobutane, 1,1-dimethylsilacyclopentane, 1,1-dimethylsilacyclohexane, 4,4-dimethyl-1-oxa-4-silacyclohexane, 1-ethyl-1-methylsilacyclobutane, 1-methyl-1-propylsilacyclobutane, 1-butyl-1-methylsilacyclobutane, 1-hexyl-1-methylsilacyclobutane, 1-methyl-1-octylsilacyclobutane, etc. can be mentioned.
[0262] Polysilalkylenesiloxanes are synthesized, for example, by polycondensation of 1,2-bis(chlorodimethylsilyl)ethane or by ring-opening polymerization of 2,2,5,5-tetramethyl-2,5-disila-1-oxacyclopentane (Org. Lett., Vol. 8, No. 21, 2006, 4683).
[0263] The monomer used in the polycondensation may be a dichlorosilane compound or a dialkoxysilane compound. For example, 1,2-bis(chlorodimethylsilyl)ethane, 1,3-bis(chlorodimethylsilyl)propane, 1,6-bis(chlorodimethylsilyl)hexane, 1,8-bis(chlorodimethylsilyl)octane, 1,2-bis(methoxydimethylsilyl)ethane, 1,3-bis(methoxydimethylsilyl)propane, 1,6-bis(methoxydimethylsilyl)hexane, 1,8-bis(methoxydimethylsilyl)octane, etc. may be mentioned.
[0264] The monomer used in the ring-opening polymerization may be a cyclic silalkylenesiloxane compound, such as 2,2,5,5-tetramethyl-2,5-disila-1-oxacyclopentane, 2,2,6,6-tetramethyl-2,6-disila-1-oxacyclohexane, 2,2,4,4,6,6,8,8-octamethyl-2,4,6,8-tetrasila-1,5-dioxacyclooctane, etc.
[0265] After the ring-opening polymerization or polycondensation, the resulting polysilalkylene or polysilalkylenesiloxane can be reacted with a compound having a reactive silane group to introduce an olefin into the terminal of the compound having a silalkylene structure. As the compound having a reactive silane group, a monochlorosilane compound can be used.
[0266] Examples of the monochlorosilane compound include monochlorosilane compounds having an olefin structure at the terminal, such as those shown below.
[0267] [ka]
[0268] Next, the compound represented by the following formula (1a-1) or (2a-1): R S1 -R 61 -CH=CH2(1a-1) CH2=CH-R 61 -R S2 -R 61 -CH=CH2(2a-1) [In the formula, R S1 and R S2 is R in formulas (1) and (2). S1 and R S2 is equivalent to R 61 is a single bond or a divalent organic group. and a compound represented by formula (4): HSiR60 3(4) [In the formula, R 60 are each independently a halogen atom (e.g., I, Br, Cl, F, etc.) or C 1-6 is an alkoxy group. and a compound represented by the following formula (1a-2) or (2a-2): R S1 -R 61 -CH2CH2-SiR 60 3(1a-2) R 60 3Si-CH2CH2-R 61 -R S2 -R 61 -CH2CH2-SiR 60 3(2a-2) [In the formula, each symbol has the same meaning as above.] Then, the compound represented by formula (1a-2) or (2a-2) is reacted with a compound represented by the following formula (5): Hal-JR 62 -CH=CH2(5) [In formula: Hal is a halogen atom (e.g., I, Br, Cl, F, etc.); J is Mg, Cu, Pd or Zn; R 62 is a bond or C 1-12 is an alkylene group. By reacting with a compound represented by the following formula (1a-3) or (2a-3): R S1 -R 61’ -Si(R 62 -CH=CH2)3(1a-3) (CH=CH2-R 62 )3Si-R 61’ -R S2 -R 61’ -Si(R 62 -CH=CH2)3(2a-3) [In the formula, R 61’ is a divalent organic group, The other symbols are as defined above.] Next, the compound represented by formula (1a-3) or (2a-3) is reacted with a compound represented by the following formula (6): HSiR 63 m R 64 3-m (6) [In the formula, R 63 are each independently a hydroxyl group or a hydrolyzable group, R 64 are each independently a monovalent organic group, m is 1 to 3. By reacting with a compound represented by formula (1-1) or (2-1): R S1 -R 61’ -Si(R 62’ -SiR 63 m R 64 3-m )3(1-1) (R 63 m R 64 3-m Si-R 62’ )3Si-R 61’ -R S2 -R 61’ -Si(R 62’ -SiR 63 m R 64 3-m )3(2-2) [In the formula, R 62’ is C 2-14 is an alkylene group, The other symbols are as defined above.] It is possible to obtain a silane compound represented by the following formula:
[0269] As an alternative method, a carbonyl group can be introduced at the end of a compound having a silalkylene structure by reacting the polysilalkylene or polysilalkylenesiloxane obtained above with a compound having a reactive silane group.
[0270] The compound having a reactive silane group is, for example, a compound represented by the formula: R 74 Si(R 71 )2-R 72 -COOR 73 [In formula: R 71 each independently represents a halogen atom; 1-12 Alkyl groups, preferably C 1-6 Alkyl groups, more preferably C 1-3 an alkyl group, more preferably a methyl group; R 72 may be substituted by a halogen atom; C 2-12 Alkylene group, preferably C 3-5 is an alkylene group, R 73 may be substituted by a hydrogen atom or a halogen atom; C 1-3 an alkyl group, preferably a methyl group or an ethyl group, more preferably a methyl group; R 74 is a halogen atom, a hydroxyl group, or a hydrolyzable group, preferably a halogen atom or a hydroxyl group, more preferably a chlorine atom or a hydroxyl group. The compound represented by the formula: The alkyl group may be linear or branched. The alkyl group is preferably unsubstituted. The alkylene group may be linear or branched, but is preferably linear. The alkylene group is preferably unsubstituted. The halogen atom is, for example, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and is preferably a chlorine atom.
[0271] Specifically, examples of the compound having a reactive silane group include compounds having a monochlorosilane having an ester structure at the terminal, as shown below. [ka]
[0272] Next, the compound represented by the following formula (1b-1) or (2b-1): R S1 -R 61-COOR 65 (1b-1) R 65 OCO-R 61 -R S2 -R 61 -COOR 65 (2b-1) [In the formula, R S1 and R S2 is R in formulas (1) and (2). S1 and R S2 is equivalent to R 61 is a single bond or a divalent organic group, R 65 is a hydrogen atom or C 1-6 is an alkyl group. and a compound represented by formula (7): NH2-R 66 -C(R 62 -CH=CH2)3(7) [In the formula, R 62 is a single bond or C 1-12 is an alkylene group, R 66 is a single bond or C 1-12 is an alkylene group. and a compound represented by the following formula (1b-2) or (2b-2): R S1 -R 61 -CONH-R 66 -C(R 62 -CH=CH2)3(1b-2) (CH=CH2-R 62 )3C-R 66 -NHCO-R 61 -R S2 -R 61 -CONH-R 66 -C(R 62 -CH=CH2)3(2b-2) [In the formula, each symbol has the same meaning as above.] Then, the compound represented by formula (1b-2) or (2b-2) is reacted with a compound represented by the following formula (6): HSiR 63 m R64 3-m (6) [In the formula, R 63 are each independently a hydroxyl group or a hydrolyzable group, R 64 are each independently a monovalent organic group, m is 1 to 3. By reacting with a compound represented by formula (1-2) or (2-2): R S1 -R 61 -CONH-R 66 -C(R 62’ -SiR 63 m R 64 3-m )3(1-2) (R 63 m R 64 3-m Si-R 62’ )3C-R 66 -NHCO-R 61 -R S2 -R 61 -CONH-R 66 -C(R 62’ -SiR 63 m R 64 3-m )3(2-2) [In the formula, R 62’ is C 2-14 is an alkylene group, The other symbols are as defined above.] It is possible to obtain a silane compound represented by the following formula:
[0273] Alternatively, the compound represented by the following formula (1b-1) or (2b-1): R S1 -R 61 -COOR 65 (1b-1) R 65 OCO-R 61 -R S2 -R 61 -COOR 65 (2b-1) [In the formula, R S1 and R S2 is R in formulas (1) and (2). S1 and R S2 is equivalent to R 61 is C 1-12 is an alkylene group, R 65 is a hydrogen atom or C 1-6 is an alkyl group. and a compound represented by formula (8): HN(R 62 -CH=CH2)2(8) [In the formula, R 62 is C 1-12 is an alkylene group. and a compound represented by the following formula (1c-2) or (2c-2): R S1 -R 61 -CON(R 62 -CH=CH2)2(1c-2) (CH=CH2-R 62 )2NCO-R 61 -R S2 -R 61 -CON(R 62 -CH=CH2)2(2c-2) [In the formula, each symbol has the same meaning as above.] Then, the compound represented by formula (1c-2) or (2c-2) is reacted with a compound represented by the following formula (6): HSiR 63 m R 64 3-m (6) [In the formula, R 63 are each independently a hydroxyl group or a hydrolyzable group, R 64 are each independently a monovalent organic group, m is 1 to 3. By reacting with a compound represented by formula (1-3) or (2-3): R S1 -R 61 -CON(R62’ -SiR 63 m R 64 3-m )2(1-3) (R 63 m R 64 3-m Si-R 62’ )2NCO-R 61 -R S2 -R 61 -CON(R 62’ -SiR 63 m R 64 3-m )2(2-3) [In the formula, R 62’ is C 2-14 is an alkylene group, The other symbols are as defined above.] It is possible to obtain a silane compound represented by the following formula:
[0274] Alternatively, the compound represented by the following formula (1b-1) or (2b-1): R S1 -R 61 -COOR 65 (1b-1) R 65 OCO-R 61 -R S2 -R 61 -COOR 65 (2b-1) [In the formula, R S1 and R S2 is R in formulas (1) and (2). S1 and R S2 is equivalent to R 61 is C 1-12 is an alkylene group, R 65 is a hydrogen atom or C 1-6 is an alkyl group. The compound represented by MR 62 -CH=CH2 [In formula: M is a metal-containing group such as Li, halogen-Mg, or Zn; R 62 is C 1-12 is an alkylene group. and reacting the compound represented by the following formula (1d-2) or (2d-2): R S1 -R 61 -C(OH)(R 62 -CH=CH2)2(1d-2) (CH=CH2-R 62 )2(OH)CR 61 -R S2 -R 61 -C(OH)(R 62 -CH=CH2)2(2d-2) [In the formula, each symbol has the same meaning as above.] Next, the compound represented by formula (1d-2) or (2d-2) is reacted with a compound represented by the following formula (6): HSiR 63 m R 64 3-m (6) [In the formula, R 63 are each independently a hydroxyl group or a hydrolyzable group, R 64 are each independently a monovalent organic group, m is 1 to 3. By reacting with a compound represented by formula (1-4) or (2-4): R S1 -R 61 -C(OH)(R 62’ -SiR 63 m R 64 3-m )2(1-4) (R 63 m R 64 3-m Si-R 62’ )2(OH)CR 61 -R S2 -R 61 -C(OH)(R 62’ -SiR 63 mR 64 3-m )2(2-4) [In the formula, R 62’ is C 2-14 is an alkylene group, The other symbols have the same meanings as above.] It is possible to obtain a silane compound represented by the following formula:
[0275] Alternatively, the following formula (1d-2) or (2d-2): R S1 -R 61 -C(OH)(R 62 -CH=CH2)2(1d-2) (CH=CH2-R 62 )2(OH)CR 61 -R S2 -R 61 -C(OH)(R 62 -CH=CH2)2(2d-2) [In the formula, each symbol has the same meaning as above.] The compound represented by the formula (I) is reacted with an olefination agent, for example, R 69 -R 68 -CH=CH2 [In the formula, R 68 is C 1-12 is an alkylene group, R 69 is a halogen atom, for example a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and is preferably a bromine atom. and a compound represented by the following formula (1e-1) or (2e-1): R S1 -R 61 -C(OR 68 -CH=CH2)(R 62 -CH=CH2)2(1e-1) (CH=CH2-R 62 )2(CH=CH2-R 68 O)CR 61 -R S2 -R 61 -C(OR 68 -CH=CH2)(R 62-CH=CH2)2(2e-1) [In the formula, each symbol has the same meaning as above.] Then, the compound represented by formula (1e-1) or (2e-1) is reacted with the compound represented by formula (6): HSiR 63 m R 64 3-m (6) [In the formula, R 63 are each independently a hydroxyl group or a hydrolyzable group, R 64 are each independently a monovalent organic group, m is 1 to 3. By reacting with a compound represented by formula (1-5) or (2-5): R S1 -R 61 -C(OR 62’ -SiR 63 m R 64 3-m )(R 62’ -SiR 63 m R 64 3-m )2(1-5) (R 63 m R 64 3-m Si-R 62’ )2(SiR 63 m R 64 3-m -R 62’ O)CR 61 -R S2 -R 61 -C(OR 62’ -SiR 63 m R 64 3-m )(R 62’ -SiR 63 m R 64 3-m )2(2-5) [In the formula, R 62’ are each independently 2-14is an alkylene group, The other symbols have the same meanings as above.] It is possible to obtain a silane compound represented by the following formula:
[0276] Alternatively, the following formula (1d-2) or (2d-2): R S1 -R 61 -C(OH)(R 62 -CH=CH2)2(1d-2) (CH=CH2-R 62 )2(OH)CR 61 -R S2 -R 61 -C(OH)(R 62 -CH=CH2)2(2d-2) [In the formula, each symbol has the same meaning as above.] The compound represented by the formula (I) is reacted with a polyether group-introducing agent, for example R 78 -R 75 -(OR 76 ) x -R 77 [In the formula, R 75 is C 1-6 is an alkylene group, R 76 is C 1-6 is an alkylene group, R 77 is a hydrogen atom, a hydroxyl group, or C 1-6 is an alkyl group, R 78 is a halogen atom, for example a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, preferably a chlorine atom; x is an integer from 0 to 20. and a compound represented by the following formula (1f-1) or (2f-1): R S1 -R 61 -C(OR 79 )(R 62 -CH=CH2)2(1d-2) (CH=CH2-R 62 )2(R 79 O)CR 61 -RS2 -R 61 -C(OR 79 )(R 62 -CH=CH2)2(2d-2) [In formula: R 79 -R 75 -(OR 76 ) x -R 77 and The other symbols have the same meanings as above.] Then, the compound represented by formula (1f-1) or (2f-1) is reacted with the compound represented by formula (6): HSiR 63 m R 64 3-m (6) [In the formula, R 63 are each independently a hydroxyl group or a hydrolyzable group, R 64 are each independently a monovalent organic group, m is 1 to 3. By reacting with a compound represented by formula (1-6) or (2-6): R S1 -R 61 -C(OR 79 )(R 62’ -SiR 63 m R 64 3-m )2(1-6) (R 63 m R 64 3-m Si-R 62’ )2(R 79 O)CR 61 -R S2 -R 61 -C(OR 79 )(R 62’ -SiR 63 m R 64 3-m )2(2-6) [In the formula, R 62’ are each independently 2-14is an alkylene group, The other symbols have the same meanings as above.] It is possible to obtain a silane compound represented by the following formula:
[0277] The present disclosure provides the following as a production intermediate of at least one silane compound represented by formula (1) or (2): In the following formulas, the same symbols as those in formulas (1) and (2) represent the same as those in formulas (1) and (2) and have the same aspects.
[0278] Formula (1a-3) or (2a-3): R S1 -R 61’ -Si(R 62 -CH=CH2)3(1a-3) (CH=CH2-R 62 )3Si-R 61’ -R S2 -R 61’ -Si(R 62 -CH=CH2)3(2a-3) [In the formula, R S1 are each independently R 1 -R S -SiR 2 2- and R S2 -R S -SiR 2 2- and R S are each independently represented by the following formula: [ka] (In the formula: R 3 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 4 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 6 are each independently 1-6 is an alkylene group, R 7 each independently represents an optionally substituted phenylene group or naphthylene group, R 8 each independently represents a single bond or C 1-6 is an alkylene group, R 9 are each independently a single bond or an oxygen atom; R 5 are each independently a hydrocarbon group; x is an integer from 0 to 200; y is an integer from 0 to 200; z is an integer from 0 to 200; y+z is greater than or equal to 1, The order of occurrence of each repeating unit enclosed in parentheses with x, y, or z is arbitrary in the formula. is a group represented by R 1 is a hydrocarbon group, R 2 are each independently a hydrocarbon group; R 62 is a single bond or C 1-12 is an alkylene group, R 61’ is a divalent organic group. A compound represented by the formula:
[0279] Formula (1b-1) or (2b-1): R S1 -R 61 -COOR 65 (1b-1) R 65 OCO-R 61 -R S2 -R 61 -COOR 65 (2b-1) [In the formula, R S1 are each independently R 1 -R S -SiR 2 2- and R S2 -R S -SiR 2 2- and R S are each independently represented by the following formula: [ka] (In the formula: R 3 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 4 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 6 are each independently 1-6 is an alkylene group, R 7 each independently represents an optionally substituted phenylene group or naphthylene group, R 8 each independently represents a single bond or C 1-6 is an alkylene group, R 9 are each independently a single bond or an oxygen atom; R 5are each independently a hydrocarbon group; x is an integer from 0 to 200; y is an integer from 0 to 200; z is an integer from 0 to 200; y+z is greater than or equal to 1, The order of occurrence of each repeating unit enclosed in parentheses with x, y, or z is arbitrary in the formula. is a group represented by R 1 is a hydrocarbon group, R 2 are each independently a hydrocarbon group; R 61 is a single bond or a divalent organic group, R 65 is a hydrogen atom or C 1-6 is an alkyl group. A compound represented by the formula:
[0280] Formula (1b-2) or (2b-2): R S1 -R 61 -CONR 67 -R 66 -C(R 62 -CH=CH2)3(1b-2) (CH=CH2-R 62 )3C-R 66 -NR 67 CO-R 61 -R S2 -R 61 -CONR 67 -R 66 -C(R 62 -CH=CH2)3(2b-2) [In the formula, R S1 are each independently R 1 -R S -SiR 2 2- and R S2 -R S -SiR 2 2- and R S are each independently represented by the following formula: [ka] (In the formula: R 3 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 4 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 6 are each independently 1-6 is an alkylene group, R 7 each independently represents an optionally substituted arylene group, R 8 each independently represents a single bond or C 1-6 is an alkylene group, R 9 are each independently a single bond or an oxygen atom; R 5 are each independently a hydrocarbon group; x is an integer from 0 to 200; y is an integer from 0 to 200; z is an integer from 0 to 200; y+z is greater than or equal to 1, The order of occurrence of each repeating unit enclosed in parentheses with x, y, or z is arbitrary in the formula. is a group represented by R 1 is a hydrocarbon group, R 2 are each independently a hydrocarbon group; R 61 is a single bond or a divalent organic group (preferably C 1-12 alkylene group), R 62 is a single bond or C 1-12 is an alkylene group, R 66 is a single bond or C 1-12 is an alkylene group, R 67 is a hydrogen atom, C 1-18 It is an alkyl group, an aryl group, or a polyether group. A compound represented by the formula:
[0281] Formula (1c-2) or (2c-2): R S1 -R 61 -CON(R 62 -CH=CH2)2(1c-2) (CH=CH2-R 62 )2NCO-R 61 -R S2 -R 61-CON(R 62 -CH=CH2)2(2c-2) [In the formula, R S1 are each independently R 1 -R S -SiR 2 2- and R S2 -R S -SiR 2 2- and R S are each independently represented by the following formula: [ka] (In the formula: R 3 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 4 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 6 are each independently 1-6 is an alkylene group, R 7 each independently represents an optionally substituted arylene group, R 8 each independently represents a single bond or C 1-6 is an alkylene group, R 9 are each independently a single bond or an oxygen atom; R 5 are each independently a hydrocarbon group; x is an integer from 0 to 200; y is an integer from 0 to 200; z is an integer from 0 to 200; y+z is greater than or equal to 1, The order of occurrence of each repeating unit enclosed in parentheses with x, y, or z is arbitrary in the formula. is a group represented by R 1 is a hydrocarbon group, R 2 are each independently a hydrocarbon group; R 61 is a single bond or a divalent organic group (preferably C 1-12 alkylene group), R 62 is a single bond or C 1-12 is an alkylene group. A compound represented by the formula:
[0282] Formula (1d-2) or (2d-2): R S1 -R61 -C(OH)(R 62 -CH=CH2)2(1d-2) (CH=CH2-R 62 )2(OH)CR 61 -R S2 -R 61 -C(OH)(R 62 -CH=CH2)2(2d-2) [In the formula, R S1 are each independently R 1 -R S -SiR 2 2- and R S2 -R S -SiR 2 2- and R S are each independently represented by the following formula: [ka] (In the formula: R 3 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 4 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8-R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 6 are each independently 1-6 is an alkylene group, R 7 each independently represents an optionally substituted arylene group, R 8 each independently represents a single bond or C 1-6 is an alkylene group, R 9 are each independently a single bond or an oxygen atom; R 5 are each independently a hydrocarbon group; x is an integer from 0 to 200; y is an integer from 0 to 200; z is an integer from 0 to 200; y+z is greater than or equal to 1, The order of occurrence of each repeating unit enclosed in parentheses with x, y, or z is arbitrary in the formula. is a group represented by R 1 is a hydrocarbon group, R 2 are each independently a hydrocarbon group; R 61 is a single bond or a divalent organic group (preferably C 1-12 alkylene group), R 62 is a single bond or C1-12 is an alkylene group. A compound represented by the formula:
[0283] In the above formula, R 61 is a divalent organic group. In one embodiment, R 61 is a single bond. In another embodiment, R 61 is a divalent organic group. The divalent organic group is preferably 0-12 Alkylene group -CONH-C 0-12 Alkylene group or C 1-12 It is an alkylene group.
[0284] In the above formula, R 61’ is a divalent organic group. In one embodiment, R 61’ is C 0-12 Alkylene group -CONH-C 2-14 Alkylene group or C 2-14 It is an alkylene group.
[0285] In the above formula, R 62 is a single bond or C 1-12 It is an alkylene group.
[0286] In the above formula, R 65 is a hydrogen atom or C 1-6 It is an alkyl group.
[0287] In the above formula, R 66 is a hydrogen atom or C 1-6 It is an alkyl group.
[0288] R 67 is a hydrogen atom, C 1-18 It is an alkyl group, an aryl group, or a polyether group.
[0289] Next, the surface treatment agent of the present invention will be described.
[0290] The surface treatment agent of the present disclosure contains at least one silane compound represented by formula (1) or (2).
[0291] In one embodiment, the silane compound in the surface treatment agent of the present disclosure is a compound represented by formula (1).
[0292] In another embodiment, in the surface treatment agent of the present disclosure, the silane compound is a compound represented by formula (2).
[0293] In another embodiment, in the surface treatment agent of the present disclosure, the silane compound is a compound represented by formula (1) and a compound represented by formula (2).
[0294] In the surface treatment agent of the present disclosure, the compound represented by formula (2) is preferably 0.1 mol% or more and 35 mol% or less with respect to the total of the compound represented by formula (1) and the compound represented by formula (2). The lower limit of the content of the compound represented by formula (2) with respect to the total of the compound represented by formula (1) and the compound represented by formula (2) may be preferably 0.1 mol%, more preferably 0.2 mol%, even more preferably 0.5 mol%, even more preferably 1 mol%, particularly preferably 2 mol%, and especially 5 mol%. The upper limit of the content of the compound represented by formula (2) with respect to the total of the compound represented by formula (1) and the compound represented by formula (2) may be preferably 35 mol%, more preferably 30 mol%, even more preferably 20 mol%, even more preferably 15 mol% or 10 mol%. The proportion of the compound represented by formula (2) relative to the total of the compound represented by formula (1) and the compound represented by formula (2) is preferably 0.1 mol% or more and 30 mol% or less, more preferably 0.1 mol% or more and 20 mol% or less, even more preferably 0.2 mol% or more and 10 mol% or less, still more preferably 0.5 mol% or more and 10 mol% or less, particularly preferably 1 mol% or more and 10 mol% or less, for example, 2 mol% or more and 10 mol% or less, or 5 mol% or more and 10 mol% or less.
[0295] In one embodiment, the content of the compound represented by the above formula (1) or (2) may be preferably 0.1 to 50.0 mass%, more preferably 1.0 to 30.0 mass%, even more preferably 5.0 to 25.0 mass%, and particularly preferably 10.0 to 20.0 mass%, based on the total mass of the surface treatment agent.
[0296] In another embodiment, the content of the compound represented by the above formula (1) or (2) may be preferably 0.001 to 30 mass%, more preferably 0.01 to 10 mass%, even more preferably 0.05 to 5 mass%, and particularly preferably 0.05 to 2 mass%, based on the total mass of the surface treatment agent.
[0297] In one embodiment, the surface treatment agent of the present disclosure contains at least one of the silane compound of the present disclosure and a condensate in which at least a portion of the silane compound of the present disclosure is condensed.
[0298] The surface treatment agent of the present disclosure may include a solvent, a (non-reactive) silicone compound that may be understood as silicone oil (hereinafter referred to as "silicone oil"), an amine compound, an alcohol, a catalyst, a surfactant, a polymerization inhibitor, a sensitizer, and the like.
[0299] Examples of the solvent include 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; methyl acetate, ethyl acetate, propyl acetate, n-butyl acetate, isopropyl acetate, isobutyl acetate, cellosolve acetate, propylene glycol methyl ether acetate, carbitol acetate, diethyl oxalate, ethyl pyruvate, ethyl 2-hydroxybutyrate, and ethyl acetoacetate. esters such as acetone, amyl acetate, methyl lactate, ethyl lactate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 2-hydroxyisobutyrate, ethyl 2-hydroxyisobutyrate; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, 2-hexanone, cyclohexanone, methyl amino ketone, 2-heptanone; ethyl cellosolve, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether, propylene glycol monoethyl ether, Glycol ethers such as 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, iso-propanol, n-butanol, isobutanol, tert-butanol, sec-butanol, 3-pentanol, octyl alcohol, 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; and ethers such as cyclopentyl methyl ether.Examples of the solvent include siloxanes such as hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, octamethylcyclotetrasiloxane, and decamethylcyclopentasiloxane; fluorine-containing solvents such as 1,1,2-trichloro-1,2,2-trifluoroethane, 1,2-dichloro-1,1,2,2-tetrafluoroethane, dimethylsulfoxide, 1,1-dichloro-1,2,2,3,3-pentafluoropropane (HCFC225), Zeorola H, 1,3-bis(trifluoromethyl)benzene, HFE7100, HFE7200, HFE7300, CF3CH2OH, CF3CF2CH2OH, and (CF3)2CHOH; or mixed solvents of two or more of these solvents;
[0300] The silicone oil is not particularly limited, but may be, for example, a silicone oil represented by the following general formula (3a): R 1a -(SiR 3a 2-O) a1 -SiR 3a 2-R 1a (3a) [In formula: R 1a are each independently a hydrogen atom or a hydrocarbon group, R 3a are each independently a hydrogen atom or a hydrocarbon group, a1 is 2 to 3000. Examples of the compound include compounds represented by the following formula:
[0301] Above R 3a are each independently a hydrogen atom or a hydrocarbon group. Such a hydrocarbon group may be substituted.
[0302] 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.
[0303] R 3a each independently is preferably C optionally substituted by a halogen atom1-6 An alkyl group or an aryl group, more preferably C 1-6 It is an alkyl group or an aryl group.
[0304] Above C 1-6 The alkyl group may be straight-chain or branched-chain, but is preferably straight-chain. C 1-6 The alkyl group is preferably C 1-3 It is preferably an alkyl group, more preferably a methyl group.
[0305] The aryl group is preferably a phenyl group.
[0306] In one embodiment, R 3a are each independently 1-6 Alkyl groups, preferably C 1-3 It is preferably an alkyl group, more preferably a methyl group.
[0307] In another embodiment, R 3a is a phenyl group.
[0308] In another embodiment, R 3a is a methyl group or a phenyl group, preferably a methyl group.
[0309] Above R 1a are each independently a hydrogen atom or a hydrocarbon group, and 3a This has the same meaning as:
[0310] R 1a each independently is preferably C optionally substituted by a halogen atom 1-6 An alkyl group or an aryl group, more preferably C 1-6 It is an alkyl group or an aryl group.
[0311] In one embodiment, R 1a are each independently 1-6 Alkyl groups, preferably C 1-3 It is preferably an alkyl group, more preferably a methyl group.
[0312] In another embodiment, R 1a is a phenyl group.
[0313] In another embodiment, R 1a is a methyl group or a phenyl group, preferably a methyl group.
[0314] The above a1 is 2 to 1500. a1 may be preferably 5 or more, more preferably 10 or more, even more preferably 15 or more, for example 30 or more, or 50 or more. a1 may be preferably 1000 or less, more preferably 500 or less, even more preferably 200 or less, even more preferably 150 or less, for example 100 or less, or 80 or less.
[0315] a1 may be preferably 5-1000, more preferably 10-500, further preferably 15-200, and even more preferably 15-150.
[0316] Another silicone oil is (3b) below: R 1a -R S2 -R 3a (3b) [In formula: R 1a are each independently a hydrocarbon group; R 3a are each independently a hydrocarbon group; R S2 has the same meaning as in formula (2). Examples of the compound include compounds represented by the following formula:
[0317] The silicone oil may have an average molecular weight of 500 to 1,000,000, and preferably 1,000 to 100,000. The molecular weight of the silicone oil can be measured using GPC.
[0318] The silicone oil may be, for example, -(SiR 3a 2-O) a1A linear or cyclic silicone oil having an a1 of 30 or less can be used. The linear silicone oil may be a so-called straight silicone oil or a modified silicone oil. Examples of the straight silicone oil include dimethyl silicone oil, methylphenyl silicone oil, and methylhydrogen silicone oil. Examples of the modified silicone oil include straight silicone oil modified with alkyl, aralkyl, polyether, higher fatty acid ester, fluoroalkyl, amino, epoxy, carboxyl, alcohol, and the like. Examples of the cyclic silicone oil include cyclic dimethylsiloxane oil.
[0319] The silicone oil may be contained in an amount of, for example, 0 to 50 mass %, preferably 0.001 to 30 mass %, and more preferably 0.1 to 5 mass %, relative to the surface treatment agent of the present disclosure.
[0320] In the surface treatment agent of the present disclosure, such silicone oil may be contained in an amount of, for example, 0 to 300 parts by mass, preferably 0 to 100 parts by mass, more preferably 0 to 50 parts by mass, and even more preferably 0 to 10 parts by mass, relative to a total of 100 parts by mass of the silane compounds of the present disclosure (when two or more types are used, the total of these, the same applies below).
[0321] The silicone oil contributes to improving the surface slipperiness of the surface treatment layer.
[0322] Examples of the alcohols include alcohols having 1 to 6 carbon atoms which may be substituted with one or more fluorine atoms, such as methanol, ethanol, iso-propanol, tert-butanol, CF3CH2OH, CF3CF2CH2OH, and (CF3)2CHOH. By adding these alcohols to the surface treatment agent, the stability of the surface treatment agent is improved, and the compatibility of the persilane compound with the solvent is also improved.
[0323] Examples of the catalyst include acids (e.g., acetic acid, hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, sulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid, etc.), bases (e.g., sodium hydroxide, potassium hydroxide, ammonia, triethylamine, diethylamine, etc.), transition metals (e.g., Ti, Ni, Sn, Zr, Al, B, Si, Ta, Nb, Mo, W, Cr, Hf, V, etc.), sulfur-containing compounds having an unshared electron pair in the molecular structure, or nitrogen-containing compounds (e.g., sulfoxide compounds, aliphatic amine compounds, aromatic amine compounds, phosphoric acid amide compounds, amide compounds, urea compounds), etc.
[0324] Examples of the aliphatic amine compound include diethylamine, triethylamine, etc. Examples of the aromatic amine compound include aniline, pyridine, etc.
[0325] In a preferred embodiment, the transition metal is contained as a transition metal compound represented by MR (wherein M is a transition metal atom and R is a hydrolyzable group). By making the transition metal compound a compound in which a transition metal is bonded to a hydrolyzable group, the transition metal atom can be contained more efficiently in the surface treatment layer, and the friction durability and chemical resistance of the surface treatment layer can be further improved.
[0326] The hydrolyzable group means a group that can undergo hydrolysis, similar to the hydrolyzable group related to the silane compound, that is, a group that can be eliminated from a transition metal atom by hydrolysis. Examples of the hydrolyzable group include -OR m , -OCOR m , -ON=CR m 2, -NR m 2, -NHR m , -NCO, halogen (wherein R m is a substituted or unsubstituted C 1-4 (representing an alkyl group) and the like.
[0327] In a preferred embodiment, the hydrolyzable group is -OR mBy using an alkoxy group as the hydrolyzable group, the transition metal atom can be more efficiently incorporated into the surface treatment layer, and the friction durability and chemical resistance of the surface treatment layer can be further improved.
[0328] In one embodiment, the hydrolyzable group may be the same as the hydrolyzable group contained in the silane compound. By making the hydrolyzable groups in the silane compound and the transition metal compound the same group, even if such hydrolyzable groups are exchanged with each other, the influence can be reduced.
[0329] In another embodiment, the hydrolyzable group may be different from the hydrolyzable group contained in the silane compound. By making the hydrolyzable groups in the silane compound and the transition metal compound different, the hydrolysis reactivity can be controlled.
[0330] In one embodiment, the hydrolyzable group and the hydrolyzable group contained in the silane compound may be interchangeable in the surface treatment agent.
[0331] In a preferred embodiment, the transition metal compound is Ta(OR m )5, preferably Ta(OCH2CH3)5.
[0332] The catalyst may be contained in an amount of, for example, 0.0002% by mass or more based on the entire surface treatment agent. The catalyst is preferably contained in an amount of 0.02% by mass or more based on the entire surface treatment agent, and more preferably contained in an amount of 0.04% by mass or more based on the entire surface treatment agent. The catalyst may be contained in an amount of, for example, 10% by mass or less based on the entire surface treatment agent, and particularly 1% by mass or less. The surface treatment agent of the present disclosure may contribute to the formation of a surface treatment layer with better durability by containing the catalyst in the above-mentioned concentration.
[0333] The content of the catalyst is preferably 0 to 10% by mass, more preferably 0 to 5% by mass, and particularly preferably 0 to 1% by mass, based on the silane compound of the present disclosure.
[0334] The catalyst promotes the hydrolysis and dehydration condensation of the silane compound of the present disclosure, and promotes the formation of the layer formed by the surface treatment agent of the present disclosure.
[0335] Other examples of the other components include tetraethoxysilane, methyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, and methyltriacetoxysilane in addition to the above.
[0336] In addition to the components described above, the surface treatment agent of the present disclosure may contain trace amounts of impurities such as Pt, Rh, Ru, 1,3-divinyltetramethyldisiloxane, triphenylphosphine, NaCl, KCl, and silane condensates.
[0337] In one embodiment, the surface treatment agent of the present disclosure is for dry coating methods, preferably vacuum deposition.
[0338] In one embodiment, the surface treatment agent of the present disclosure is for use in a wet coating method, preferably dip coating.
[0339] The surface treatment agent of the present disclosure can be impregnated into a porous material, such as a porous ceramic material or a metal fiber, such as steel wool, and formed into a pellet. The pellet can be used, for example, in vacuum deposition.
[0340] The articles of the present disclosure are described below.
[0341] The article of the present disclosure includes a substrate and a layer (surface treatment layer) formed on the surface of the substrate from the surface treatment agent of the present disclosure.
[0342] Substrates that can be used in the present disclosure may be made of any suitable material, such as glass, resin (which may be a natural or synthetic resin, for example, a general plastic material), metal, ceramics, semiconductors (silicon, germanium, etc.), fibers (woven fabrics, nonwoven fabrics, etc.), fur, leather, wood, ceramics, stone, etc., building materials, etc., sanitary products, etc.
[0343] For example, when the article to be manufactured is an optical member, the material constituting the surface of the substrate may be a material for optical members, such as glass or transparent plastic. When the article to be manufactured is an optical member, the surface (outermost layer) of the substrate may have some layer (or film), such as a hard coat layer or an anti-reflection layer. The anti-reflection layer may be either a single-layer anti-reflection layer or a multi-layer anti-reflection layer. Examples of inorganic substances that can be used for the anti-reflection layer include SiO2, SiO, ZrO2, TiO2, TiO, Ti2O3, Ti2O5, Al2O3, Ta2O5, Ta3O5, Nb2O5, HfO2, Si3N4, CeO2, MgO, Y2O3, SnO2, MgF2, and WO3. These inorganic substances may be used alone or in combination of two or more of them (for example, as a mixture). When a multi-layer anti-reflection layer is used, it is preferable to use SiO2 and / or SiO for the outermost layer. When the product to be manufactured is an optical glass part for a touch panel, a transparent electrode, for example, a thin film using indium tin oxide (ITO) or indium zinc oxide, may be provided on a part of the surface of the substrate (glass). In addition, the substrate may have an insulating layer, an adhesive layer, a protective layer, a decorative frame layer (I-CON), an atomizing film layer, a hard coating film layer, a polarizing film, a phase difference film, a liquid crystal display module, etc., depending on the specific specifications.
[0344] The shape of the substrate is not particularly limited, and may be, for example, a plate, a film, or other form. The surface region of the substrate on which the surface treatment layer is to be formed may be at least a part of the substrate surface, and may be appropriately determined according to the application and specific specifications of the product to be manufactured.
[0345] In one embodiment, the substrate may be made of a material that originally has hydroxyl groups at least on its surface. Examples of such materials include glass, metals (particularly base metals), ceramics, semiconductors, etc., on whose surfaces natural oxide films or thermal oxide films are formed. Alternatively, in cases where the substrate has insufficient hydroxyl groups, such as resins, or where the substrate does not originally have hydroxyl groups, the substrate may be subjected to some pretreatment to introduce or increase the number of hydroxyl groups on the substrate surface. Examples of such pretreatment include plasma treatment (e.g., corona discharge) and ion beam irradiation. Plasma treatment can introduce or increase hydroxyl groups on the substrate surface, and can also be suitably used to clean the substrate surface (remove foreign matter, etc.). Another example of such pretreatment is a method in which an interface adsorbent having a carbon-carbon unsaturated bond group is formed in advance in the form of a monomolecular film on the substrate surface by the LB method (Langmuir-Blodgett method) or chemical adsorption method, and then the unsaturated bond is cleaved in an atmosphere containing oxygen, nitrogen, etc.
[0346] In another embodiment, the substrate may be one in which at least the surface portion is made of a material containing another reactive group, such as a silicone compound having one or more Si-H groups, or an alkoxysilane.
[0347] In a preferred embodiment, the substrate is glass, preferably sapphire glass, soda-lime glass, alkali aluminosilicate glass, borosilicate glass, alkali-free glass, crystal glass, or quartz glass, more preferably chemically strengthened soda-lime glass, chemically strengthened alkali aluminosilicate glass, or chemically bonded borosilicate glass.
[0348] The article of the present disclosure can be produced by forming a layer of the surface treatment agent of the present disclosure on the surface of the substrate, and then post-treating this layer as necessary, thereby forming a layer from the surface treatment agent of the present disclosure.
[0349] The layer formation of the surface treatment agent of the present disclosure can be carried out by applying the surface treatment agent to the surface of the substrate so as to coat the surface. The coating method is not particularly limited. For example, a wet coating method and a dry coating method can be used.
[0350] Examples of wet coating methods include dip coating, spin coating, flow coating, spray coating, roll coating, gravure coating, wipe coating, squeegee coating, die coating, ink jet, casting, Langmuir-Blodgett coating, and the like.
[0351] Examples of dry coating methods include deposition (usually vacuum deposition), sputtering, CVD, and similar methods. Specific examples of deposition methods (usually vacuum deposition) include resistance heating, electron beam, high frequency heating such as with microwaves, ion beam, and similar methods. Specific examples of CVD methods include plasma-CVD, optical CVD, thermal CVD, and similar methods.
[0352] Furthermore, coating by atmospheric pressure plasma method is also possible.
[0353] When using the wet coating method, the surface treatment agent of the present disclosure may be diluted with a solvent and then applied to the substrate surface. From the viewpoint of the stability of the composition of the present disclosure and the volatility of the solvent, the following solvents are preferably used: aliphatic hydrocarbons such as hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, mineral spirits, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, naphthalene, solvent naphtha, etc.; methyl acetate, ethyl acetate, propyl acetate, n-butyl acetate, isopropyl acetate, isobutyl acetate, cellosolve acetate, propylene glycol methyl ether acetate, carby acetate, etc. Esters such as ethyl 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, ethyl 2-hydroxyisobutyrate; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, 2-hexanone, cyclohexanone, methyl amino ketone, 2-heptanone; ethyl cellosolve, methyl cellosol glycol ethers such as 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, isopropanol, n-butanol, isobutanol, tert-butanol, sec-butanol, 3-pentanol, octyl alcohol, 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 (e.g., 1,3-bis(trifluoromethyl)benzene); polyfluoroaliphatic hydrocarbons (e.g., C6F; 13 CH2CH3 (e.g., Asahiklin® AC-6000 manufactured by Asahi Glass Co., Ltd.), 1,1,2,2,3,3,4-heptafluorocyclopentane (e.g., Zeorora® H manufactured by Zeon Corporation); hydrofluoroethers (HFEs) (e.g., perfluoropropyl methyl ether (C3F7OCH3) (e.g., Novec® 7000 manufactured by Sumitomo 3M Limited), perfluorobutyl methyl ether (C4F9OCH3) (e.g., Novec® 7100 manufactured by Sumitomo 3M Limited), perfluorobutyl ethyl ether (C4F9OC2H5) (e.g., Novec® 7 manufactured by Sumitomo 3M Limited), 200), alkyl perfluoroalkyl ethers (perfluoroalkyl groups and alkyl groups may be linear or branched) such as perfluorohexyl methyl ether (C2F5CF(OCH3)C3F7) (e.g., Novec (trademark) 7300 manufactured by Sumitomo 3M Limited), or ether alcohols such as CF3CH2OCF2CHF2 (e.g., Asahiklin (registered trademark) AE-3000 manufactured by Asahi Glass Co., Ltd.), cyclopentyl methyl ether, and the like; siloxanes such as hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, octamethylcyclotetrasiloxane, and octamethylcyclopentasiloxane. These solvents can be used alone or as a mixture of two or more kinds. Among them, hydrofluoroethers are preferred, and perfluorobutyl methyl ether (C4F9OCH3) and / or perfluorobutyl ethyl ether (C4F9OC2H5) are particularly preferred.
[0354] When the dry coating method is used, the surface treatment agent of the present disclosure may be subjected to the dry coating method as it is, or may be subjected to the dry coating method after being diluted with the above-mentioned solvent.
[0355] The layer formation of the surface treatment agent is preferably carried out so that the surface treatment agent of the present disclosure is present together with a catalyst for hydrolysis and dehydration condensation in the layer. Conveniently, in the case of the wet coating method, the surface treatment agent of the present disclosure may be diluted with a solvent, and then a catalyst may be added to the diluted solution of the surface treatment agent of the present disclosure immediately before application to the substrate surface. In the case of the dry coating method, the surface treatment agent of the present disclosure to which the catalyst has been added may be directly subjected to deposition (usually vacuum deposition) treatment, or a metal porous body such as iron or copper may be subjected to deposition (usually vacuum deposition) treatment using a pellet-shaped material impregnated with the surface treatment agent of the present disclosure to which the catalyst has been added.
[0356] The catalyst may be any suitable acid or base, transition metal (e.g., Ti, Ni, Sn, Zr, Al, B, etc.), sulfur-containing compound having an unshared electron pair in the molecular structure, or nitrogen-containing compound (e.g., sulfoxide compound, aliphatic amine compound, aromatic amine compound, phosphoric acid amide compound, amide compound, urea compound), etc. The acid catalyst may be, for example, acetic acid, formic acid, trifluoroacetic acid, hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, sulfonic acid, methanesulfonic acid, p-toluenesulfonic acid, etc. The base catalyst may be, for example, ammonia, sodium hydroxide, potassium hydroxide, organic amines such as triethylamine, diethylamine, etc. The transition metal, aliphatic amine compound, and aromatic amine compound may be the same as those described above.
[0357] The surface treatment layer included in the article of the present disclosure has both high abrasion resistance.In addition to high abrasion resistance, the surface treatment layer may have water repellency, oil repellency, antifouling properties (for example, preventing adhesion of dirt such as fingerprints), waterproof properties (preventing water from penetrating into electronic components, etc.), surface slipperiness (or lubricity, for example, wiping off dirt such as fingerprints, and excellent tactile sensation against fingers), chemical resistance, etc., depending on the composition of the surface treatment agent used, and may be suitably used as a functional thin film.
[0358] Therefore, the present disclosure further relates to an optical material having the above-mentioned surface treatment layer as the outermost layer.
[0359] Preferred examples of the optical material include optical materials relating to displays and the like, such as those exemplified below, as well as a wide variety of other optical materials: for example, displays such as cathode ray tubes (CRTs; for example, personal computer monitors), liquid crystal displays, plasma displays, organic electroluminescence displays, inorganic thin-film electroluminescence dot matrix displays, rear projection displays, vacuum fluorescent displays (VFDs), field emission displays (FEDs), and other displays, protective plates for such displays, or displays whose surfaces have been treated with an anti-reflection film.
[0360] The article of the present disclosure may be, but is not limited to, an optical member. Examples of optical members include lenses for glasses, front protection plates, anti-reflection plates, polarizing plates, and anti-glare plates for displays such as PDPs and LCDs, touch panel sheets for devices such as mobile phones and personal digital assistants, disc surfaces for optical discs such as Blu-ray (registered trademark) discs, DVD discs, CD-Rs, and MOs, optical fibers, and display surfaces for watches.
[0361] The article of the present disclosure may be a medical device or medical material. The article having a layer obtained by the present disclosure may be an automobile interior or exterior member. Examples of exterior materials include windows, light covers, and exterior camera covers. Examples of interior materials include instrument panel covers, navigation system touch panels, and decorative interior materials.
[0362] The thickness of the layer is not particularly limited. In the case of an optical member, the thickness of the layer is preferably in the range of 1 to 50 nm, 1 to 30 nm, and more preferably 1 to 15 nm, from the viewpoints of optical performance, abrasion resistance, and antifouling properties.
[0363] The compounds, compositions, and articles of the present disclosure have been described in detail above. Note that the compounds, compositions, and articles of the present disclosure are not limited to those exemplified above. EXAMPLES
[0364] The present disclosure will be described below with reference to examples, but the present disclosure is not limited to the following examples.
[0365] (Synthesis Example 0) 1,1-dimethylsilacyclobutane (3.75 g), THF (3.75 g), and n-hexane (3.75 g) were added to a glass container. The reaction solution was cooled to -50°C, and n-butyllithium / hexane solution (1.82 mL) was added and stirred for 1 hour to carry out a polymerization reaction. Allylchlorodimethylsilane (0.52 g) was then added and stirred at the same temperature for 30 minutes. The reaction solution obtained was warmed to room temperature, and water and toluene were added to separate and extract the organic layer, which was then dried over sodium sulfate. After filtration, the filtrate was concentrated and dried to obtain the following polysilalkylene group-containing compound (A) CH3CH2CH2CH2(Si(CH3)2CH2CH2CH2) n Obtained Si(CH3)2CH2CH=CH2 (3.84 g, Mw: 4468, Mw / Mn: 1.43).
[0366] Compound (A) [ka]
[0367] 1 H NMR (C6D6, 400 MHz) δ[ppm]: 0.01-0.14 (m), 0.04-0.15 (m), 0.47-0.56 (m), 0.56-0.85 (m), 0.88-0.97 (m), 1.23-1.40 (m), 1.41-1.58 (m), 1.59-1.71 (m), 4.82-5.00 (m), 5.69-5.89 (m).
[0368] (Example) (Synthesis Example 1) Compound (A) obtained in Synthesis Example 0: CH3CH2CH2CH2(Si(CH3)2CH2CH2CH2) n1.51g of Si(CH3)2CH2CH=CH2, 1.5mL of toluene, 0.023g of triacetoxymethylsilane, and 0.1mL of a xylene solution containing 2% Pt complex of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane were added, followed by 0.4mL of trichlorosilane, which was heated to 60°C and stirred for 3 hours. After that, the volatile matter was distilled off under reduced pressure, 1.2mL of toluene was added, and the mixture was cooled to below 5°C in an ice bath, and 4mL of allyl magnesium chloride (tetrahydrofuran solution, approximately 1.0mol / L) was added and stirred at room temperature for a day and night. After that, purification was performed to obtain the following polysilalkylene group-containing compound (B)CH3CH2CH2CH2(Si(CH3)2CH2CH2CH2) n 1.25 g of Si(CH3)2CH2CH2CH2Si(CH2CH=CH2)3 was obtained.
[0369] Compound (B) [ka] (n≒50)
[0370] 1 H NMR (CDCl3, 400 MHz) δ[ppm]: -0.209-0.166 (m), 0.371-0.739 (m), 0.861-0.989 (m), 1.211-1.403 (m), 1.432-1.722 (m), 4.799-5.090 (m), 5.723-5.832 (m)
[0371] (Synthesis Example 2) Polysilalkylene group-containing compound (B) CH3CH2CH2CH2(Si(CH3)2CH2CH2CH2) obtained in Synthesis Example 1 n1.22g of Si(CH3)2CH2CH2CH2Si(CH2CH=CH2)3, 1.2ml of toluene, 0.015g of triacetoxymethylsilane, and 0.084g of a xylene solution containing 2% Pt complex of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane were added, and then 0.4mL of trichlorosilane was charged, heated to 60°C, and stirred for 3 hours. After that, volatile matter was distilled off under reduced pressure, and then 1.2mL of toluene was added, and a mixed solution of 0.06g of methanol and 1.24g of trimethyl orthoformate was added, and then heated to 50°C and stirred for 3 hours. After that, purification was performed to obtain the following polysilalkylene group-containing compound (C)CH3CH2CH2CH2(Si(CH3)2CH2CH2CH2) having a trimethoxysilyl group at the end. n 1.19 g of Si(CH3)2CH2CH2CH2Si(CH2CH2CH2Si(OCH3)3) was obtained.
[0372] Polysilalkylene Group-Containing Compound (C) [ka] (n≒50)
[0373] 1 H NMR (CDCl3, 400 MHz) δ[ppm]: -0.211-0.090 (m), 0.368-0.607 (m), 0.645-0.734 (m), 0.859-0.894 (t), 0.928-0.965 (t), 1.109-1.386 (m), 1.418-1.677 (m), 3.421-3.760 (m)
[0374] (Synthesis Example 3) 5 g of 1,2-bis(chlorodimethylsilyl)ethane, 1.5 mL of toluene, and 0.84 mL of water were added, and the mixture was heated to 100°C and stirred for 8 hours to carry out a polycondensation reaction. After purification, 3.13 g of allylchlorodimethylsilane and 2.76 g of pyridine were added and stirred at room temperature for 30 minutes. The resulting reaction liquid was concentrated under reduced pressure and washed with acetonitrile to obtain the following polysilalkylenesiloxane group-containing compound (D)CH2=CHCH2(CH3)2SiO(Si(CH3)2CH2CH2Si(CH3)2O). n 3.5 g of Si(CH3)2CH2CH=CH2 was obtained.
[0375] Polysilalkylenesiloxane Group-Containing Compound (D) [ka] (n≒25)
[0376] 1 H NMR (CDCl3, 400 MHz) δ[ppm]: -0.094-0.292 (m), 0.346-0.788 (m), 1.533-1.573 (d), 4.837-4.905 (m), 5.738-5.846 (m)
[0377] (Synthesis Example 4) Polysilalkylenesiloxane group-containing compound (D) obtained in Synthesis Example 3 CH2=CHCH2(CH3)2SiO(Si(CH3)2CH2CH2Si(CH3)2O) n2.0g of Si(CH3)2CH2CH=CH2, 2.0mL of toluene, 0.013g of triacetoxymethylsilane, and 0.1mL of xylene solution containing 2% Pt complex of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane were added, followed by 0.4mL of trichlorosilane, which was heated to 60℃ and stirred for 3 hours. After that, volatile matter was distilled off under reduced pressure, 2.0mL of toluene was added, the mixture was cooled to 5℃ or less in an ice bath, 8.0mL of allyl magnesium chloride (tetrahydrofuran solution, about 1.0mol / L) was added, and the mixture was stirred at room temperature for a day and night. After that, the product was purified to obtain the following polysilalkylenesiloxane group-containing compound (E)(CH2=CHCH2)3SiCH2CH2CH2(CH3)2SiO(Si(CH3)2CH2CH2Si(CH3)2O) n 2.00 g of Si(CH3)2CH2CH2CH2Si(CH2CH=CH2) was obtained.
[0378] Polysilalkylenesiloxane Group-Containing Compound (E) [ka] (n≒25)
[0379] 1 H NMR (CDCl3, 400 MHz) δ[ppm]: -0.114-0.263 (m), 0.393-0.415 (m), 0.585-0.678 (m), 1.255-1.434 (m), 1.535-1.593 (m), 4.842-5.037 (m), 5.734-5.837 (m)
[0380] (Synthesis Example 5) Polysilalkylenesiloxane group-containing compound (E) (CH2=CHCH2)3SiCH2CH2CH2(CH3)2SiO(Si(CH3)2CH2CH2Si(CH3)2O) obtained in Synthesis Example 4 n1.97g of Si(CH3)2CH2CH2CH2Si(CH2CH=CH2)3, 1.2ml of toluene, 0.017g of triacetoxymethylsilane, and 0.084g of a xylene solution containing 2% Pt complex of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane were added, followed by 0.4mL of trichlorosilane, which was then heated to 60°C and stirred for 3 hours. After that, the volatile matter was distilled off under reduced pressure, and then 1.2mL of toluene was added, followed by a mixed solution of 0.11g of methanol and 1.50g of trimethyl orthoformate, which was then heated to 50°C and stirred for 3 hours. After that, purification was performed to obtain the following polysilalkylenesiloxane group-containing compound (F) having a terminal trimethoxysilyl group ((CH3O)3SiCH2CH2CH2)3SiCH2CH2CH2(CH3)2SiO(Si(CH3)2CH2CH2Si(CH3)2O) n 2.02 g of Si(CH3)2CH2CH2CH2Si(CH2CH2CH2Si(OCH3)3) was obtained.
[0381] Polysilalkylenesiloxane group-containing compound (F) [ka] (n≒25)
[0382] 1 H NMR (CDCl3, 400 MHz) δ[ppm]:-0.122-0.174 (m), 0.313-0.440 (m), 0.472-0.744(m), 0.855-1.030 (m), 1.247-1.701 (m), 3.421-3.474 (m), 3.497-3.641 (m)
[0383] (Synthesis Example 6) 0.085g of triethylsilanol, 0.049g of 1,5,7-triazabicyclo[4.4.0]dec-5-ene, and 15.6mL of tetrahydrofuran were added, followed by 5.02g of 2,2,5,5-tetramethyl-1,2,5-oxadisilorane, and stirred at 30°C for 3 hours. 0.11g of benzoic acid was added, and after purification, 5mL of THF was added, 0.94mL of allylchlorodimethylsilane, and 0.81mL of pyridine were added, and stirred at 30°C for 15 minutes. The resulting reaction solution was concentrated under reduced pressure and washed with acetonitrile to obtain the following polysilalkylenesiloxane group-containing compound (G) (CH3CH2)3SiO(Si(CH3)2CH2CH2Si(CH3)2O) n 3.84 g of Si(CH3)2CH2CH=CH2 was obtained.
[0384] Polysilalkylenesiloxane Group-Containing Compound (G) [ka] (n≒32)
[0385] 1 H NMR (CDCl3, 400 MHz) δ[ppm]:0.004-0.277 (m), 0.332-0.575 (m), 0.911-0.950 (t), 1.542-1.590 (m), 4.800-4.895 (m), 5.730-5.838 (m)
[0386] (Synthesis Example 7) Polysilalkylenesiloxane group-containing compound (G) (CH3CH2)3SiO(Si(CH3)2CH2CH2Si(CH3)2O) obtained in Synthesis Example 6 n2.01g of Si(CH3)2CH2CH=CH2, 2.0mL of toluene, 0.013g of triacetoxymethylsilane, and 0.075g of a xylene solution containing 2% Pt complex of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane were added, followed by 0.5mL of trichlorosilane, which was heated to 60°C and stirred for 3 hours. After that, the volatile matter was distilled off under reduced pressure, 2.0mL of toluene was added, the mixture was cooled to 5°C or less in an ice bath, 8.0mL of allyl magnesium chloride (tetrahydrofuran solution, approximately 1.0mol / L) was added, and the mixture was stirred at room temperature for a day and night. After that, the product was purified to obtain the following polysilalkylenesiloxane group-containing compound (H)(CH3CH2)3SiO(Si(CH3)2CH2CH2Si(CH3)2O) n 1.95 g of Si(CH3)2CH2CH2CH2Si(CH2CH=CH2) was obtained.
[0387] Polysilalkylenesiloxane group-containing compound (H) [ka] (n≒32)
[0388] 1 H NMR (CDCl3, 400 MHz) δ[ppm]:-0.115-0.185 (m), 0.321-0.678 (m), 0.903-0.942 (t), 1.255-1.432 (m), 1.511-1.677 (m), 4.797-4.902 (m), 5.727-5.841 (m)
[0389] (Synthesis Example 8) Polysilalkylenesiloxane group-containing compound (H) (CH3CH2)3SiO(Si(CH3)2CH2CH2Si(CH3)2O) obtained in Synthesis Example 7 n1.91g of Si(CH3)2CH2CH2CH2Si(CH2CH=CH2)3, 2.0ml of toluene, 0.0098g of triacetoxymethylsilane, and 0.17g of xylene solution containing 2% Pt complex of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane were added, and then 0.5mL of trichlorosilane was charged, heated to 60°C, and stirred for 3 hours. After that, volatile matter was distilled off under reduced pressure, and then 2.0mL of toluene was added, and a mixed solution of 0.11g of methanol and 2.37g of trimethyl orthoformate was added, and then heated to 50°C and stirred for 3 hours. After that, by purification, the following polysilalkylenesiloxane group-containing compound (I) (CH3CH2)3SiO(Si(CH3)2CH2CH2Si(CH3)2O) having a trimethoxysilyl group at the end was obtained. n 2.06 g of Si(CH3)2CH2CH2CH2Si(CH2CH2CH2Si(OCH3)3) was obtained.
[0390] Polysilalkylenesiloxane Group-Containing Compound (I) [ka] (n≒32)
[0391] 1 H NMR (CDCl3, 400 MHz) δ[ppm]:-0.117-0.182 (m), 0.322-0.750 (m), 0.901-0.941 (t), 1.227-1.621 (m), 3.376-3.646 (m)
[0392] (Synthesis Example 9) Karstedt's catalyst (44.9 mg), methyl 4-pentenoate (9.93 g), and chlorodimethylsilane (10.09 g) were added to a glass sealed reaction vessel and stirred for 5 minutes at 50° C. The resulting reaction liquid was distilled under reduced pressure of 700 Pa to 800 Pa to obtain 10.5 g of the following compound (J), methyl 5-(chlorodimethylsilyl)pentanoate.
[0393] Methyl 5-(chlorodimethylsilyl)pentanoate (J) [ka]
[0394] 1 H NMR (CDCl3, 400 MHz) δ[ppm]: δ0.36 (s, 6H), 0.78-0.82 (m, 2H), 1.36-1.44 (m, 2H), 1.62 (q, J=7.6Hz, 2H), 2.26 (t, J=8.0Hz, 2H), 3.58 (s, 3H)
[0395] (Synthesis Example 10) After adding 0.84 g of triethylsilanol, 0.22 g of 1,5,7-triazabicyclo[4.4.0]dec-5-ene, and 50 mL of tetrahydrofuran, 23.5 mL of 2,2,5,5-tetramethyl-1,2,5-oxadisilorane was added and stirred at 30° C. for 3 hours. 2.96 g of pyridine and 5.21 g of methyl 5-(chlorodimethylsilyl)pentanoate obtained in Synthesis Example 9 were added and stirred at room temperature for 12 hours. The mixture was washed with a saturated aqueous sodium bicarbonate solution and purified using a silica gel column to obtain compound (L)(CH3CH2)3SiO(Si(CH3)2CH2CH2Si(CH3)2O). n Si(CH3)2CH2CH2CH2CH2COOCH3 (3.35 g) was obtained. The average number of repeating units, n, was 20.
[0396] (Compound L) [ka]
[0397] 1 H NMR (CDCl3, 400 MHz) δ[ppm]:-0.04-0.19 (m), 0.36-0.44 (m), 0.47-0.59 (m), 0.90-94 (t), 1.30-1.44 (m), 1.61-1.69 (m), 2.29-2.34 (m), 3.66-3.67 (m)
[0398] (Synthesis Example 11) Compound (L) (CH3CH2)3SiO(Si(CH3)2CH2CH2Si(CH3)2O) obtained in Synthesis Example 10 n 3.0 g of Si(CH3)2CH2CH2CH2CH2COOCH3, 6 g of tetrahydrofuran, 25 g of water, and lithium hydroxide were mixed and stirred at 50°C overnight. After that, it was washed with hydrochloric acid and concentrated under reduced pressure to obtain (CH3CH2)3SiO(Si(CH3)2CH2CH2Si(CH3)2O). n Si(CH3)2CH2CH2CH2CH2COOH was obtained. Next, 1.28 g of 4-[2,2-di(2-propylenyl)]pentenylamine, 1.49 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, and 6.5 g of dichloromethane were mixed and stirred at room temperature overnight. After that, purification was performed to obtain compound (M) (CH3CH2)3SiO(Si(CH3)2CH2CH2Si(CH3)2O). n The compound Si(CH3)2CH2CH2CH2CH2CONHCH2C(CH2CH=CH2)3 (3.23 g) was obtained. The average number of repeating units, n, was 60.
[0399] (Compound M) [ka]
[0400] 1 H NMR (CDCl3, 400 MHz) δ[ppm]:-0.05-0.05 (m), 0.34-0.40 (m), 0.43-0.51 (m), 0.87-0.90 (t), 1.07-1.15 (m), 1.18-1.35 (m), 1.58-1.77 (m), 2.14-2.20 (m), 2.24-2.32 (m), 5.01-5.08 (m), 5.74-5.88 (m)
[0401] (Synthesis Example 12) Compound (M) (CH3CH2)3SiO(Si(CH3)2CH2CH2Si(CH3)2O) obtained in Synthesis Example 11 n1.01 g of Si(CH3)2CH2CH2CH2CH2CONHCH2C(CH2CH=CH2)3, 1.74 g of toluene, 0.05 mL of pyridine, and 0.10 g of a xylene solution of Karstedt's catalyst were added, followed by 0.4 mL of trimethoxysilane and stirring at room temperature overnight. After purification, the compound (N)(CH3CH2)3SiO(Si(CH3)2CH2CH2Si(CH3)2O) with a trimethoxysilyl group at the end was obtained. n Si(CH3)2CH2CH2CH2CH2CONHCH2C(CH2CH2CH2Si(OCH3)3)3 (1.08 g) was obtained.
[0402] Compound (N) [ka]
[0403] 1 H NMR (CDCl3, 400 MHz) δ[ppm]:-0.06-0.18 (m), 0.36-0.47 (m), 0.49-0.62 (m), 0.90-0.94 (t), 1.15-1.40 (m), 1.62-1.80 (m), 2.14-2.23 (m), 3.48-3.62 (m)
[0404] (Synthesis Example 13) 1,1-dimethylsilacyclobutane (7.60 g), THF (7.60 g), and n-hexane (7.60 g) were added to a glass container. The reaction solution was cooled to -50°C, and n-butyllithium / hexane solution (3.69 mL) was added and stirred for 1 hour to carry out a polymerization reaction. Then, 5-(chlorodimethylsilyl)methyl pentanoate (1.64 g) was added and stirred at the same temperature for 30 minutes. The reaction solution obtained was warmed to room temperature, and water and toluene were added to perform liquid separation and extraction, and the organic layer was dried with sodium sulfate. After filtration, the filtrate was concentrated and dried, and then purified with a silica gel column using hexane as a developing solvent to obtain the following polysilalkylene group-containing compound (P)CH3CH2CH2CH2(Si(CH3)2CH2CH2CH2) nSi(CH3)2CH2CH2CH2CH2COOCH3 (2.60 g, Mw: 5652, Mw / Mn: 1.31) was obtained.
[0405] (Compound P) [ka]
[0406] 1 H NMR (C6D6, 400 MHz) δ[ppm]: 0.01-0.14 (m), 0.04-0.15 (m), 0.47-0.56 (m), 0.56-0.85 (m), 0.88-0.97 (m), 1.23-1.40 (m), 1.41-1.58 (m), 1.59-1.71 (m), 2.29-2.34 (m), 3.66-3.67 (m)
[0407] (Synthesis Example 14) Compound (P)CH3CH2CH2CH2(Si(CH3)2CH2CH2CH2) obtained in Synthesis Example 13 n 2.0 g of Si(CH3)2CH2CH2CH2CH2COOCH3, 2.5 g of tetrahydrofuran, 11 g of water, and lithium hydroxide were mixed and stirred at 50°C overnight. After that, it was washed with hydrochloric acid and concentrated under reduced pressure to obtain CH3CH2CH2CH2(Si(CH3)2CH2CH2CH2) n Si(CH3)2CH2CH2CH2CH2COOH was obtained. Next, 0.53 g of 4-[2,2-di(2-propylenyl)]pentenylamine, 0.62 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, and 2.7 g of dichloromethane were mixed and stirred at room temperature overnight. After that, purification was performed to obtain compound (Q)CH3CH2CH2CH2(Si(CH3)2CH2CH2CH2) n Si(CH3)2CH2CH2CH2CH2CONHCH2C(CH2CH=CH2)3 (2.15 g, Mw: 6769, Mw / Mn: 1.37) was obtained.
[0408] (Compound Q) [ka]
[0409] 1 H NMR (CDCl3, 400 MHz) δ[ppm]: -0.209-0.166 (m), 0.371-0.739 (m), 0.861-0.989 (m), 1.211-1.403 (m), 1.432-1.722 (m), 2.14-2.20 (m), 2.24-2.32 (m), 5.01-5.08 (m), 5.74-5.88 (m)
[0410] (Synthesis Example 15) Compound (Q) CH3CH2CH2CH2(Si(CH3)2CH2CH2CH2) obtained in Synthesis Example 14 n 2.00 g of Si(CH3)2CH2CH2CH2CH2CONHCH2C(CH2CH=CH2)3, 2.0 g of toluene, 0.05 mL of pyridine, and 0.11 g of a xylene solution of Karstedt's catalyst were added, followed by 0.4 mL of trimethoxysilane and stirring at room temperature overnight. After purification, the compound (R)CH3CH2CH2CH2(Si(CH3)2CH2CH2CH2) having a trimethoxysilyl group at the end was obtained. n Si(CH3)2CH2CH2CH2CH2CONHCH2C(CH2CH2CH2Si(OCH3)3)3 (1.08 g, Mw: 7586, Mw / Mn: 1.35) was obtained.
[0411] (Compound R) [ka]
[0412] 1H NMR (CDCl3, 400 MHz) δ[ppm]: -0.211-0.090 (m), 0.368-0.607 (m), 0.645-0.734 (m), 0.859-0.894 (t), 0.928-0.965 (t), 1.109-1.386 (m), 1.418-1.677 (m), 2.14-2.23 (m), 3.48-3.62 (m)
[0413] Comparative Example 1 As a comparative compound, the following compound (O) was prepared. [ka]
[0414] <Formation of surface treatment layer> The compounds (C), (F), (I), (N) and (R) obtained above, as well as the comparative compound (O) were diluted to a concentration of 20 wt % in 1,3-bis(trifluoromethyl)benzene to obtain surface treatment agents 1 to 6. The surface treatment agents 1 to 6 prepared above were vacuum-deposited onto chemically strengthened glass (Corning Gorilla Glass, thickness 0.7 mm). Specifically, 0.1 g of the surface treatment agent was loaded into a molybdenum boat in a vacuum deposition apparatus, and the inside of the vacuum deposition apparatus was pressurized to a pressure of 3.0 × 10 -3 The chamber was evacuated to less than 100 Pa. After that, silicon dioxide was evaporated to a thickness of 7 nm by electron beam evaporation to form a silicon dioxide film, and the boat was then heated by resistance heating to form a surface treatment layer.
[0415] <Evaluation> [Wear resistance evaluation] The higher the static contact angle of water after the abrasion resistance test, the smaller the deterioration of performance due to friction and the more excellent the abrasion resistance. (Initial evaluation) As an initial evaluation (number of frictions: 0), after the surface treatment layer was formed, excess water on the surface was wiped off, and then the static contact angle of water was measured. (Evaluation after abrasion resistance test) The surface treatment layer thus formed was rubbed back and forth with a rubbing tester (manufactured by Imoto Manufacturing Co., Ltd.) under the following conditions. After a certain number of rubs, the static contact angle of water was measured. The results are shown in the table below. Friction element: BEMCOT M-3II (product name, manufactured by Asahi Kasei Corporation) Travel distance (one way): 60mm Traveling speed: 8,400mm / min Load: 100g / 3cm 2
[0416] [Table 1] [Industrial Applicability]
[0417] The surface treatment agent of the present disclosure can be suitably used for a wide variety of applications.
Claims
1. The following formula (1) or (2): 【Chemistry 1】 [In the formula: R S2 is, -R S -SiR 2 2 - and R S Each of these is independent and expressed by the following formula: 【Chemistry 2】 (In the formula: R 3 is, independently of each other, C 1-12 alkylene group, -R 6 -O-R 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 -, or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 -, and is R 4 Each of them is independent of C 1-12 Alkylene group, -R 6 -O-R 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 -, or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 6 Each of them is independent of C 1-6 It is an alkylene group, R 7 These are, independently, arylene groups which may be substituted, R 8 Each of these is independently a single bond, or C 1-6 It is an alkylene group, R 9 Each of these is independently a single bond or an oxygen atom. R 5 Each of these is independently a hydrocarbon group, x is an integer between 0 and 200. y is an integer between 0 and 200. z is an integer between 0 and 200. y + z is greater than or equal to 1. The order in which each repeating unit, denoted by x, y, or z and enclosed in parentheses, exists is arbitrary within the formula. It is a base represented by, R 2 Each of these is independently a hydrocarbon group, R H These are, independently, the following equations (S1), (S3), (S4), or (S5): 【Transformation 3】 [In the formula: R 11 These are, independently, hydroxyl groups or hydrolyzable groups, R 12 Each of these is independently a monovalent organic group, n1 is (SiR 11 n1 R 12 3-n1 Each unit is an independent integer between 0 and 3. X 11 Each of these is independently a single bond or a divalent organic group. R 13 Each of these is independently a hydrogen atom or a monovalent organic group. Each t is an independent integer greater than or equal to 2. R 14 Each of these is independently a hydrogen atom, a halogen atom, or -X 11 -SiR 11 n1 R 12 3-n1 And, R 15 Each of these is independently a single bond, an oxygen atom, an alkylene group having 1 to 6 carbon atoms, or an alkylene oxy group having 1 to 6 carbon atoms. R a1 Each of these is independently of -Z 1 -SiR 21 p1 R 22 q1 R 23 r1 And; Z 1 is, independently of each other, a divalent organic group, R 21 is, independently of each other, -Z 1’ -SiR 21’ p1’ R 22’ q1’ R 23’ r1’ and; R 22 These are, independently, hydroxyl groups or hydrolyzable groups, R 23 Each of these is independently a monovalent organic group, p1 is an integer between 0 and 3, independently of each other. Each of q1 is an integer between 0 and 3, independently of the others. Each r1 is an independent integer between 0 and 3. Z 1’ These are, independently, divalent organic groups, R 21’ Each of these is independently of -Z 1” -SiR 22” q1” R 23” r1” And; R 22’ These are, independently, hydroxyl groups or hydrolyzable groups, R 23’ Each of these is independently a monovalent organic group, p1' are each independent integers between 0 and 3. Each of q1' is an independent integer between 0 and 3. r1' are each independent integers between 0 and 3. Z 1” These are, independently, divalent organic groups, R 22” These are, independently, hydroxyl groups or hydrolyzable groups, R 23” Each of these is independently a monovalent organic group, Each of q1'' is an independent integer between 0 and 3. Each of r1'' is an independent integer between 0 and 3. R b1 These are, independently, hydroxyl groups or hydrolyzable groups, R c1 Each of these is independently a monovalent organic group, k1 is an integer between 0 and 3, independently of each other. l1 are each an independent integer between 0 and 3. Each of the m1 values is an integer between 0 and 3, independently of the others. However, in formula (S3), there are at least two Si atoms to which a hydroxyl group or a hydrolyzable group is bonded, R d1 Each of these is independently of -Z 2 -CR 31 p2 R 32 q2 R 33 r2 And, Z 2 Each of these is independently a single bond, an oxygen atom, or a divalent organic group. R 31 Each of these is independently of -Z 2’ -CR 32’ q2’ R 33’ r2’ And, R 32 Each of these is independently of -Z 3 -SiR 34 n2 R 35 3-n2 And, R 33 Each of these is independently a hydrogen atom, a hydroxyl group, or a monovalent organic group. p2 is an integer between 0 and 3, independently of each other. Each of the q2 values is an integer between 0 and 3, independently of the others. Each of the r2 values is an integer between 0 and 3, independently of the others. Z 2’ Each of these is independently a single bond, an oxygen atom, or a divalent organic group. R 32’ Each of these is independently of -Z 3 -SiR 34 n2 R 35 3-n2 And, R 33’ Each of these is independently a hydrogen atom, a hydroxyl group, or a monovalent organic group. Each of q2' is an integer between 0 and 3, independently of the others. r2' are each independent integers between 0 and 3. Z 3 Each of these is independently a single bond, an oxygen atom, or a divalent organic group; R 34 These are, independently, hydroxyl groups or hydrolyzable groups, R 35 Each of these is independently a monovalent organic group, n2 are each an independent integer between 0 and 3. R e1 Each of these is independently of -Z 3 -SiR 34 n2 R 35 3-n2 And, R f1 Each of these is independently a hydrogen atom, a hydroxyl group, or a monovalent organic group. k2 are each an independent integer between 0 and 3. l2 are each an independent integer between 0 and 3. Each of the values of m2 is an independent integer between 0 and 3. However, in formula (S4), there are at least two Si atoms to which a hydroxyl group or a hydrolyzable group is bonded, R g1 and R h1 Each of these is independently of -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 And, Z 4 Each of these is independently a single bond, an oxygen atom, or a divalent organic group. However, in formula (S5), there are at least two Si atoms to which a hydroxyl group or a hydrolyzable group is bonded. It is a base represented by, X A These are, independently, 2-10 valent organic groups, Each of the γ values is an independent integer between 1 and 9. A silane compound represented by the formula.
2. The following formula (1) or (2): 【Chemistry 4】 [In the formula: R S2 is, -R S -SiR 2 2 - and R S Each of these is independent and expressed by the following formula: 【Transformation 5】 (In the formula: R 3 Each of them is independent of C 1-12 Alkylene group, -R 6 -O-R 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 -, or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 4 Each of them is independent of C 1-12 Alkylene group, -R 6 -O-R 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 -, or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 6 Each of them is independent of C 1-6 It is an alkylene group, R 7 These are, independently, arylene groups which may be substituted, R 8 Each of these is independently a single bond, or C 1-6 It is an alkylene group, R 9 Each of these is independently a single bond or an oxygen atom. R 5 Each of these is independently a hydrocarbon group, x is an integer between 0 and 200. y is an integer between 0 and 200. z is an integer between 0 and 200. y + z is greater than or equal to 1. The order in which each repeating unit, denoted by x, y, or z and enclosed in parentheses, exists is arbitrary within the formula. It is a base represented by, R 2 Each of these is independently a hydrocarbon group, R H Each of these independently corresponds to the following equation (S2): 【Transformation 6】 [In the formula: R 11 These are, independently, hydroxyl groups or hydrolyzable groups, R 12 Each of these is independently a monovalent organic group, n1 is (SiR 11 n1 R 12 3-n1 Each unit is an independent integer between 0 and 3. It is a base represented by, X A Each of these is independent and expressed by the following formula: -(R 51 ) p5 -(X 51 ) q5 - [In the formula: R 51 is, -(CH 2 ) s5 - or o-, m- or p-phenylene group, s5 is an integer between 1 and 20. X 51 These are -O-, -S-, o-, m- or p-phenylene groups, -CO-, -C(O)O-, -CONR 54 -, -O-CONR 54 -, and -NR 54 - is a group selected from the group consisting of R 54 Each of these is independently a hydrogen atom or a monovalent organic group. n5 are each an independent integer between 1 and 20. l5 is an integer between 1 and 10. p5 is either 0 or 1. q5 is 1, Here, the order of existence of each repeating unit, enclosed in parentheses with p5 or q5, is arbitrary. It is a divalent organic group represented by γ is 1. A silane compound represented by the formula.
3. R 2 Each of these may be independently substituted with a halogen atom, C 1-18 It is an alkyl group or an aryl group, R 5 Each of these may be independently substituted with a halogen atom, C 1-18 It is an alkyl group or an aryl group. The compound according to claim 1 or 2.
4. R 2 These are, independently, a methyl group or a phenyl group. R 5 These are, independently, a methyl group or a phenyl group. The silane compound according to claim 1 or 2.
5. R 3 Each of them is independent of C 1-12 Alkylene group, or -R 6 -O-R 6 - The silane compound according to claim 1 or 2.
6. R 4 Each of them is independent of C 1-12 Alkylene group, or -R 6 -O-R 6 - The silane compound according to claim 1 or 2.
7. R 4 Each of these is independently of -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 -, or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - The silane compound according to claim 1 or 2.
8. R H The silane compound according to claim 1, wherein each of these groups is independently represented by formula (S3), (S4), or (S5).
9. The silane compound according to claim 1, wherein γ is 1.
10. X A The formula is as follows: -(R 51 ) p5 -(X 51 ) q5 - [In the formula: R 51 is, -(CH 2 ) s5 - or o-, m- or p-phenylene group, s5 is an integer between 1 and 20. X 51 is, -(X 52 ) l5 - and X 52 These are, independently, -O-, -S-, o-, m- or p-phenylene groups, -CO-, -C(O)O-, and -CONR 54 -, -O-CONR 54 -, -NR 54 - and - (CH 2 ) n5 - is a group selected from the group consisting of R 54 Each of these is independently a hydrogen atom or a monovalent organic group. n5 are each an independent integer between 1 and 20. l5 is an integer between 1 and 10. p5 is either 0 or 1. q5 is either 0 or 1. Here, at least one of p5 and q5 is 1, and the order of existence of each repeating unit enclosed in parentheses with p5 or q5 is arbitrary. The silane compound according to claim 1, wherein the divalent organic group is represented by .
11. X A Each of them is independent of C 1-20 Alkylene group, or -(CH 2 ) s5 -CONH-(CH 2 ) t5 The silane compound according to claim 1, wherein (wherein s5 is an integer from 1 to 20, and t5 is an integer from 1 to 20).
12. A surface treatment agent containing the silane compound described in claim 1 or 2.
13. A surface treatment agent containing at least one compound comprising a silane compound according to claim 1 or 2, and a compound comprising a condensate obtained by condensing at least a portion of the silane compound.
14. A surface treatment agent according to claim 12, for use in vacuum deposition.
15. The surface treatment agent according to claim 12, which is for wet coating.
16. A pellet containing the surface treatment agent described in claim 12.
17. An article comprising a base material and a layer formed on the base material from a silane compound according to claim 1 or 2, or a surface treatment agent according to claim 13.
18. The article according to claim 17, which is an optical component.
19. The article according to claim 18, which is a display.
20. Equation (1c-2) or (2c-2): R S1 -R 61 -CON(R 62 -CH=CH 2 ) 2 (1c-2) (CH=CH 2 -R 62 ) 2 NCO-R 61 -R S2 -R 61 -CON(R 62 -CH=CH 2 ) 2 (2c-2) [In the formula, R S1 Each of them is independent of R 1 -R S -SiR 2 2 - and R S2 is, -R S -SiR 2 2 - and R S Each of these is independent and expressed by the following formula: 【Transformation 7】 (In the formula: R 3 Each of them is independent of C 1-12 Alkylene group, -R 6 -O-R 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 -, or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 4 Each of them is independent of C 1-12 Alkylene group, -R 6 -O-R 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 -, or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 6 Each of them is independent of C 1-6 It is an alkylene group, R 7 These are, independently, arylene groups which may be substituted, R 8 Each of these is independently a single bond, or C 1-6 It is an alkylene group, R 9 Each of these is independently a single bond or an oxygen atom. R 5 Each of these is independently a hydrocarbon group, x is an integer between 0 and 200. y is an integer between 0 and 200. z is an integer between 0 and 200. y + z is greater than or equal to 1. The order in which each repeating unit, denoted by x, y, or z and enclosed in parentheses, exists is arbitrary within the formula. It is a base represented by, R 1 It is a hydrocarbon group, R 2 Each of these is independently a hydrocarbon group, R 61 is a single bond, or C 1-12 It is an alkylene group, R 62 is a single bond, or C 1-12 It is an alkylene group. A compound represented by the formula.
21. Equation (1d-2) or (2d-2): R S1 -R 61 -C(OH)(R 62 -CH=CH 2 ) 2 (1d-2) (CH=CH 2 -R 62 ) 2 (OH)C-R 61 -R S2 -R 61 -C(OH)(R 62 -CH=CH 2 ) 2 (2d-2) [In the formula, R S1 Each of them is independent of R 1 -R S -SiR 2 2 - and R S2 is, -R S -SiR 2 2 - and R S Each of these is independent and expressed by the following formula: 【Transformation 8】 (In the formula: R 3 Each of them is independent of C 1-12 Alkylene group, -R 6 -O-R 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 -, or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 4 Each of them is independent of C 1-12 Alkylene group, -R 6 -O-R 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 -, or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 6 Each of them is independent of C 1-6 It is an alkylene group, R 7 These are, independently, arylene groups which may be substituted, R 8 Each of these is independently a single bond, or C 1-6 It is an alkylene group, R 9 Each of these is independently a single bond or an oxygen atom. R 5 Each of these is independently a hydrocarbon group, x is an integer between 0 and 200. y is an integer between 0 and 200. z is an integer between 0 and 200. y + z is greater than or equal to 1. The order in which each repeating unit, denoted by x, y, or z and enclosed in parentheses, exists is arbitrary within the formula. It is a base represented by, R 1 It is a hydrocarbon group, R 2 Each of these is independently a hydrocarbon group, R 61 is a single bond, or C 1-12 It is an alkylene group, R 62 is a single bond, or C 1-12 It is an alkylene group. A compound represented by the formula.
22. formula: R 74 Si(R 71 ) 2 -R 72 -COOR 73 [In the formula: R 71 Each of these C atoms may be independently substituted with a halogen atom. 1-12 It is an alkyl group, R 72 C may be substituted with a halogen atom. 4-5 It is an alkylene group, R 73 C may be substituted with a hydrogen atom or a halogen atom. 1-3 It is an alkyl group, R 74 This is a halogen atom, a hydroxyl group, or a hydrolyzable group. A compound represented by the formula.
23. R 71 It is a methyl group, R 72 is a straight chain of C 4-5 It is an alkylene group, R 73 This is a methyl group or an ethyl group, R 74 is a chlorine atom or a hydroxyl group. The compound according to claim 22.