Silane compound
The development of silane compounds with specific structural formulas addresses the issue of insufficient weather resistance in existing silane compounds by forming a surface treatment layer with enhanced weather and UV resistance.
Patent Information
- Application Number
- JP2024172904
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2023-10-02
- Filing Date
- 2024-10-02
- Publication Date
- 2025-04-14
AI Technical Summary
Existing silane compounds used for surface treatment do not provide sufficient weather resistance.
Development of silane compounds with specific structural formulas containing ether bonds and hydroxyl or hydrolyzable groups, which form a surface treatment layer with enhanced weather resistance.
The new silane compounds create a surface treatment layer with improved weather resistance and UV resistance.
Smart Images

Figure 2025062586000001 
Figure 2025062586000002 
Figure 2025062586000003
Abstract
Description
[Technical field]
[0001] The present disclosure relates to silane compounds. [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 2019-44179 A Summary of the Invention [Problem to be solved by the invention]
[0004] An object of the present disclosure is to provide a silane compound capable of forming a surface treatment layer having higher weather resistance. [Means for solving the problem]
[0005] The present disclosure includes the following aspects. [1] The following formula (1): [ka] [In formula: R S is a monovalent group containing one or more Si atoms to which a hydroxyl group or a hydrolyzable group is not directly bonded, X 1 is a divalent to decavalent group containing two or more ether bonds, R Si is a monovalent group containing a Si atom to which a hydroxyl group or a hydrolyzable group is bonded, α is an integer from 1 to 9. A compound represented by the formula: [2] R S is R 1 -R S1-(SiR 2 2 ) s - and R 1 is a hydrocarbon group, or R 1a na R 1b 3-na Si-(O) z -: R 1a are each independently R 1d -(SiR 1d 2 -R 1c ) ma - is a group represented by R 1c each independently represents an oxygen atom or C 1-6 is an alkylene group, R 1d are each independently a hydrocarbon group or R 1a’ and R 1a’ is R 1a is equivalent to Each ma is independently an integer of 1 to 5; However, R 1a Medium, R 1a’ The number of is 20 or less, R 1b are each independently a hydrocarbon group; na is an integer from 1 to 3; z is 0 or 1; R S1 are each independently a single bond or a group 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 -, -R8 -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; x+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 2 are each independently a hydrocarbon group; s is 0 or 1; The compound according to the above [1]. [3] R 1 is R 1a na R 1b 3-na Si-O-, R 1a are each independently -(R 1c -SiR 1d 2 ) ma -R 1d is a group represented by R 1c each independently represents an oxygen atom or C 1-6 is an alkylene group, R 1d are each independently a hydrocarbon group or R 1a’ and R 1a’ is R 1a is equivalent to Each ma is independently an integer of 1 to 5; However, R 1a Medium, R 1a’ The number of is 20 or less, R 1b are each independently a hydrocarbon group; na is an integer from 1 to 3; The compound according to the above [2], wherein the R is a group represented by the formula: [4] R 1a are each independently -(OSiR 1d 2 ) ma -R 1d is a group represented by R 1d are each independently a hydrocarbon group or R1a’ and Each ma is independently 1 or 2; R 1b are each independently a hydrocarbon group; na is an integer from 1 to 3; The compound according to the above [2] or [3]. [5] R 1d is C 1-4 The compound according to any one of the above [2] to [4], which is an alkyl group. [6] X 1 is -(O) z1 -[(CH 2 ) nb O] nc The compound according to any one of the above [1] to [5], which contains a group represented by the formula: - (wherein nb is an integer of 1 to 10, nc is an integer of 1 to 30, and z1 is 0 or 1). [7] X 1 is -(O) z1 -[CH 2 CH 2 O] nc The compound according to any one of the above [1] to [6], which contains a group represented by the formula: - (wherein nc is an integer of 1 to 30, and z1 is 0 or 1). [8] X 1 can further include alkylene, phenylene, -CO-, -COO-, -NR x1 -,-CONR x1 -,-OCONR x1 -, -NR x1 -CO-NR x1 -, -O-, -S-, -O-(CH 2 ) x1 -CONR x1 - or -O-(CH 2 ) x1 is a divalent organic group containing -CO-, R x1 is a hydrogen atom or C 1-6 is an alkyl group, x1 is an integer from 1 to 20; The compound according to any one of the above [1] to [7]. [9] X 1is expressed by the following formula: -X 11 -X 12 -X 13 - [In formula: X 11 is a single bond or a divalent group, X 12 is -(O) z1 -[(CH 2 ) nb O] nc - (wherein nb is an integer of 1 to 10, nc is an integer of 1 to 30, and z1 is 0 or 1), X 13 is a single bond or a divalent group. The compound according to any one of the above [1] to [8], wherein the group is represented by the following formula:
[10] R Si 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 15each 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, The sum of p1, q1 and r1 is 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, the sum of p1', q1' and r1' is 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, The sum of q1" and r1" is 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, The sum of k1, l1 and m1 is 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 353-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; The sum of p2, q2 and r2 is 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, The sum of q2' and r2' is 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. The sum of k2, l2 and m2 is 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 compound according to any one of the above [1] to [9], wherein the group is represented by the following formula:
[11] R S is expressed by the following formula: R 1 -[Si(CH 3 ) 2 -O] x -Si(CH 3 ) 2 - [In the formula, R 1 is an alkyl group having 1 to 6 carbon atoms or R 1a na R 1b 3-na Si-(O) z - and R 1a is (CH 3 ) 3 SiO-, R 1b is an alkyl group having 1 to 4 carbon atoms, na is 2 or 3; and x is an integer from 5 to 50. is a group represented by X 1 is expressed by the following formula: -X 11 -X 12 -X 13 - [In formula: X 11 is C 1-6 an alkylene group or a phenylene group, X 12 is -O-[(CH 2 ) nb O] nc - (In the formula, nb is an integer of 2 to 4, nc is an integer of 1 to 5, and z1 is 0 or 1.) is a group represented by X 13 is C 1-12 is an alkylene group. is a group represented by R Si is expressed by the following formula: -SiR 11 3 [In the formula, R 11 -OR h and R h is an alkyl group having 1 to 4 carbon atoms.] is a group represented by α is 1, The compound according to any one of the above items [1] to
[10] .
[12] The compound according to any one of the above [1] to
[11] , which is the following compound: CH 3 CH 2 CH 2 CH 2 [Si(CH 3 ) 2 O] n Si(CH 3 ) 2 CH 2 CH 2 CH 2 OCH2 CH 2 OCH 2 CH 2 CH 2 Si(OCH 3 ) 3 TIFF2025062586000004.tif31130 (wherein TMSO is (CH 3 ) 3 SiO-, and n is 3 to 100.
[13] The compound according to any one of the above [1] to
[11] , which is the following compound: CH 3 CH 2 CH 2 CH 2 [Si(CH 3 ) 2 O] n Si(CH 3 ) 2 CH 2 CH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 CH 2 Si(OCH 3 ) 3 TIFF2025062586000005.tif31130 (wherein TMSO is (CH 3 ) 3 SiO-, and n is 10 to 30.
[14] A surface treatment agent comprising the compound according to any one of the above [1] to
[13] .
[15] The surface treatment agent according to the above
[11] , further comprising a condensate of the compound according to any one of the above [1] to
[13] .
[16] The surface treatment agent according to the above
[14] or
[15] , which is for vacuum deposition.
[17] The surface treatment agent according to the above
[14] or
[15] , which is for wet coating.
[18] A pellet containing the surface treatment agent according to any one of the above items
[14] to
[17] .
[19] An article comprising a substrate and a layer formed on the substrate from the compound according to any one of the above items [1] to
[13] .
[20] The article according to
[19] above, further comprising an intermediate layer comprising silicon oxide between the substrate and the layer.
[21] The article according to
[19] or
[20] above, wherein the intermediate layer contains alkali metal atoms.
[22] The article according to
[21] above, wherein at least a portion of the alkali metal atoms are sodium atoms.
[23] The article according to any one of the above
[19] to
[22] , which is an optical member.
[24] The article according to any one of the above
[19] to
[23] , which is a display.
[25] Formula: R S -X 1a -CH=CH 2 [In formula: R S is a monovalent group containing one or more Si atoms to which a hydroxyl group or a hydrolyzable group is not directly bonded, X 1a is a divalent group containing two or more ether bonds. A compound represented by the formula:
[26] Formula: R S -X 1a -CONR 51 -(CH 2 ) x -CH=CH 2 [In formula: R S is a monovalent group containing one or more Si atoms to which a hydroxyl group or a hydrolyzable group is not directly bonded, X 1a is a divalent group containing two or more ether bonds, R 51 is a hydrogen atom or a monovalent hydrocarbon group, x is an integer from 0 to 30. The compound according to the above
[25] , Effect of the Invention
[0006] According to the present disclosure, it is possible to provide a silane compound capable of forming a surface treatment layer having higher weather resistance. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0007] 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.
[0008] 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.
[0009] 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 3-10Unsaturated cycloalkyl groups, 5-10 membered heterocyclyl groups, 5-10 membered unsaturated heterocyclyl groups, C 6-10 Examples of the alkyl group include one or more groups selected from aryl groups and 5- to 10-membered heteroaryl groups.
[0010] 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 or -NCO (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.
[0011] The silane compound of the present disclosure has the following formula (1): [ka] [In formula: R S is a monovalent group containing one or more Si atoms to which a hydroxyl group or a hydrolyzable group is not directly bonded, X 1 is a divalent to decavalent group containing two or more ether bonds, R Si is a monovalent group containing a Si atom to which a hydroxyl group or a hydrolyzable group is bonded, α is an integer from 1 to 9. It is expressed as:
[0012] The compounds of the present disclosure are1 Since the compound contains two or more ether bonds, the surface treatment layer obtained from the compound of the present disclosure can be imparted with excellent ultraviolet (UV) resistance.
[0013] R S is a monovalent group containing one or more Si atoms to which a hydroxyl group or a hydrolyzable group is not directly bonded.
[0014] In one embodiment, R S is R 1 -R S1 -(SiR 2 2 ) s - is a group represented by the formula:
[0015] R 1 is a hydrocarbon group, or R 1a na R 1b 3-na Si-(O) z -It is.
[0016] In one embodiment, R 1 is a hydrocarbon group. 1 The hydrocarbon group in the formula (I) may preferably be an alkyl group or an aryl group.
[0017] The alkyl group may be linear or branched. The alkyl group is preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms. The alkyl group is particularly preferably a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, or a tert-butyl group.
[0018] The aryl group may be monocyclic or polycyclic. The aryl is preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 10 carbon atoms. The aryl group is particularly preferably a phenyl group.
[0019] R 1 The hydrocarbon group in is preferably an alkyl group, more preferably an alkyl group having 1 to 4 carbon atoms.
[0020] In one embodiment, R 1 is R 1a na R 1b 3-na Si-(O) z -It is.
[0021] R 1a are each independently R 1d -(SiR 1d 2 -R 1c ) ma - is a group represented by the formula:
[0022] R 1c each independently represents an oxygen atom or C 1-6 It is an alkylene group.
[0023] R 1c C in 1-6 The alkylene group may be a straight chain or a branched chain. 1-6 The alkylene group is preferably 1-4 Alkylene group, more preferably C 2-4 It may be an alkylene group.
[0024] In one embodiment, R 1c is O.
[0025] In one embodiment, some R 1c is O and other R 1c is C 1-6 It is an alkylene group.
[0026] R 1d are each independently a hydrocarbon group or R 1a’ It is.
[0027] In one embodiment, R 1d is a hydrocarbon group.
[0028] R 1d The hydrocarbon group in the formula (I) may preferably be an alkyl group or an aryl group.
[0029] The alkyl group may be linear or branched. The alkyl group is preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms. The alkyl group is particularly preferably a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, or a tert-butyl group.
[0030] The aryl group may be monocyclic or polycyclic. The aryl is preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 10 carbon atoms. The aryl group is particularly preferably a phenyl group.
[0031] R 1d The hydrocarbon group in the above formula is preferably an alkyl group, more preferably an alkyl group having 1 to 4 carbon atoms.
[0032] In one embodiment, R 1d is R 1a’ It is.
[0033] R 1a’ is R 1a That is, R 1a’ is R 1d -(SiR 1d 2 -R 1c ) ma -. However, R 1a Medium, R 1a’ The number is 20 or less, preferably 10 or less, more preferably 6 or less, and further preferably 3 or less.
[0034] In one embodiment, R 1d is R 1d’ -(SiR 1d’ 2 -R 1c’ ) ma’ - [In formula: R 1d’ are each independently a hydrocarbon group or R 1d -(SiR 1d 2 -R1c ) ma - and At least one R 1d’ is R 1d -(SiR 1d 2 -R 1c ) ma - and R 1c each independently represents an oxygen atom or C 1-6 is an alkylene group, R 1d are each independently or a hydrocarbon group; Each ma is independently an integer of 1 to 5; R 1c’ each independently represents an oxygen atom or C 1-6 is an alkylene group, Each ma' is independently an integer of 1 to 5. It is.
[0035] In another embodiment, in one embodiment, R 1d is R 1d’ -(SiR 1d’ 2 -R 1c’ ) ma’ - [In formula: R 1c’ each independently represents an oxygen atom or C 1-6 is an alkylene group, R 1d’ are each independently a hydrocarbon group or R 1d” -(SiR 1d” 2 -R 1c” ) ma” - and At least one R 1d’ is R 1d” -(SiR 1d” 2 -R 1c” ) ma” - and R 1d” are each independently a hydrocarbon group or R 1d -(SiR 1d 2 -R1c ) ma - and At least one R 1d” is -(R 1c -SiR 1d 2 ) ma -R 1d and R 1c each independently represents an oxygen atom or C 1-6 is an alkylene group, R 1d are each independently or a hydrocarbon group; Each ma is independently an integer of 1 to 5; R 1c” each independently represents an oxygen atom or C 1-6 is an alkylene group, Each m is independently an integer from 1 to 5; Each ma' is independently an integer of 1 to 5. It is.
[0036] Each ma is independently an integer of 1 to 5, preferably 1 or 2.
[0037] R 1b are each independently a hydrocarbon group.
[0038] R 1b The hydrocarbon group in the formula (I) may preferably be an alkyl group or an aryl group.
[0039] The alkyl group may be linear or branched. The alkyl group is preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms. The alkyl group is particularly preferably a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, or a tert-butyl group.
[0040] The aryl group may be monocyclic or polycyclic. The aryl is preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 10 carbon atoms. The aryl group is particularly preferably a phenyl group.
[0041] R 1b is preferably an alkyl group, more preferably an alkyl group having 1 to 4 carbon atoms.
[0042] na is 1 to 3. In one embodiment, na is 2. In another embodiment, na is 3. 1a’ If present, na is (Si 1d 2 -R 1c ) ma Each is selected independently.
[0043] z is 0 or 1. In one embodiment, z is 0. In another embodiment, z is 1.
[0044] R 1a There are two or more Si—O bonds, preferably three or more, more preferably four or more, and further preferably six or more, for example eight or more, nine or more, ten or more, or twelve or more.
[0045] In a preferred embodiment, R 1a na R 1b 3-na Si-(O) z -In R 1a are each independently R 1d -(Si 1d 2 -R 1c ) ma - is a group represented by R 1c each independently represents an oxygen atom or C 1-6 is an alkylene group, R 1d are each independently a hydrocarbon group (preferably an alkyl group having 1 to 4 carbon atoms), or R 1a’and preferably a hydrocarbon group (preferably an alkyl group having 1 to 4 carbon atoms), R 1a’ is R 1a is equivalent to ma is 1 or 2, R 1b are each independently a hydrocarbon group, preferably an alkyl group having 1 to 4 carbon atoms, na is 1 to 3; z is 0 or 1, preferably 0.
[0046] R 1a na R 1b 3-na Si-(O) z Examples of groups represented by - include, but are not limited to, the following groups: [ka]
[0047] [ka]
[0048] [ka]
[0049] In one embodiment, R 1a na R 1b 3-na Si-(O) z The group represented by - is the following group. [ka]
[0050] In one embodiment, R 1a na R 1b 3-na Si-(O) z The group represented by - is the following group. [ka]
[0051] R S1 each independently represents a single bond or 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 -R9 -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; x+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 2 are each independently a hydrocarbon group; s is 0 or 1. It is a group represented by the following formula:
[0052] In one embodiment, R S1 is a single bond.
[0053] In another embodiment, R S1 teeth, [ka] It is a group represented by the following formula:
[0054] R 3 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R7 -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 -, preferably C 1-12 Alkylene group or -R 6 -OR 6 -It is.
[0055] 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.
[0056] In one embodiment, R 4 are each independently 1-12 Alkylene group or -R 6 -OR 6 -It is.
[0057] 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 -R 9 -R 7 -R 8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 -It is.
[0058] 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.
[0059] 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 -R8 - or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 -It is.
[0060] Above C 1-12 The alkylene group may be linear or branched. 1-12 The alkylene group is preferably straight-chained.
[0061] Above C 1-12 The alkylene group is preferably 2-8 Alkylene group, more preferably C 2-6 It is an alkylene group.
[0062] 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.
[0063] Above C 1-6 The alkylene group is preferably 2-4 Alkylene group, more preferably C 2-3 It is an alkylene group.
[0064] In a preferred embodiment, multiple R 6 In a group containing 6 are the same group.
[0065] R 7 each independently represents an optionally substituted arylene group.
[0066] In one embodiment, R 7 are each independently [ka] It is.
[0067] In one embodiment, R 7 is a phenylene group.
[0068] In another embodiment, R 7 is a naphthylene group.
[0069] 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.
[0070] 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.
[0071] The substituents on the arylene group are each independently -R 41 -R 42 It is.
[0072] 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.
[0073] 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.
[0074] The halogen is fluorine, chlorine, bromine or iodine, preferably fluorine.
[0075] R 42 C in 1-12 The alkyl group may be straight or branched.
[0076] R43 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.
[0077] 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.
[0078] R 45 is -CH=CH 2 or -OCOCH=CH 2 It is.
[0079] 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.
[0080] 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.
[0081] In one embodiment, R 8 is a single bond.
[0082] In another embodiment, R 8 is C 1-6 It is an alkylene group.
[0083] R 9 are each independently a single bond or an oxygen atom.
[0084] In one embodiment, R 9 is a single bond.
[0085] In another embodiment, R 9 is an oxygen atom.
[0086] R 5 are each independently a hydrocarbon group. Such a hydrocarbon group may be substituted.
[0087] 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.
[0088] 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.
[0089] 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.
[0090] The aryl group is preferably a phenyl group.
[0091] 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.
[0092] In another embodiment, R 5 is a phenyl group.
[0093] In another embodiment, R 5are each independently a methyl group or a phenyl group, preferably a methyl group.
[0094] 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.
[0095] In one embodiment, x is 0.
[0096] 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.
[0097] 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.
[0098] In one embodiment, y is 0.
[0099] 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.
[0100] 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.
[0101] In one embodiment, z is 0.
[0102] 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.
[0103] In one embodiment, y is 0 and z is 0.
[0104] R S1may be a random polymer or a block polymer.
[0105] X 1 is a divalent to decavalent group containing two or more ether bonds.
[0106] X 1 The number of ether bonds in the formula (I) may be preferably 2 to 50, more preferably 2 to 40, further preferably 2 to 30, further more preferably 2 to 20, and particularly preferably 2 to 9, for example, 2 to 6, or 2 to 5.
[0107] In one embodiment, X 1 is -(O) z1 -[(CH 2 ) nb O] nc - (wherein nb is an integer of 1 to 10, nc is an integer of 1 to 30, and z1 is 0 or 1).
[0108] nb is preferably an integer of 1 to 6, more preferably an integer of 2 to 4, and further preferably 2 or 3.
[0109] nc is preferably an integer of 1 to 25, for example, an integer of 3 to 25, an integer of 3 to 20, an integer of 3 to 10, an integer of 4 to 25, an integer of 5 to 20, an integer of 4 to 15, an integer of 5 to 15, an integer of 3 to 6, an integer of 1 to 10, an integer of 1 to 5, an integer of 1 to 4, or an integer of 1 to 3.
[0110] In one embodiment, z1 is 0. In another embodiment, z1 is 1.
[0111] In a preferred embodiment, X 1 is -(O) z1 -[CH 2 CH 2 O] nc - (wherein nc is an integer of 1 to 30, and z1 is 0 or 1).
[0112] In a preferred embodiment, X 1In addition to two or more ether bonds, alkylene, phenylene, -CO-, -COO-, -NR x1 -,-CONR x1 -,-OCONR x1 -, -NR x1 -CO-NR x1 -, -O-, -S-, -O-(CH 2 ) x1 -CONR x1 - and -O-(CH 2 ) x1 R is a group containing at least one group selected from -CO-, and is preferably a divalent group. x1 is a hydrogen atom or C 1-6 It is an alkyl group, and x1 is an integer of 1 to 20.
[0113] X 1 is preferably of the following formula: -X 11 -X 12 -X 13 - [In formula: X 11 is a single bond or a divalent group, X 12 is -(O) z1 -[(CH 2 ) nb O] nc - (wherein nb is an integer of 1 to 10, nc is an integer of 1 to 30, and z1 is 0 or 1), X 13 is a single bond or a divalent group. It is a group represented by the following formula:
[0114] X 11 is a single bond or a divalent group.
[0115] In one embodiment, X 11 is a single bond.
[0116] In one embodiment, X 11 is a divalent group.
[0117] X 11The divalent group in is an alkylene, a phenylene, -CO-, -COO-, or -NR x1 -,-CONR x1 -,-OCONR x1 -, -NR x1 -CO-NR x1 -, -O-, -S-, -O-(CH 2 ) x1 -CONR x1 - and -O-(CH 2 ) x1 R may be a group containing at least one group selected from -CO-. x1 is a hydrogen atom or C 1-6 It is an alkyl group, and x1 is an integer of 1 to 20. The alkylene may preferably have 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, for example, 1 to 10, 1 to 6, 2 to 30, 5 to 25, 10 to 25, or 12 to 20 carbon atoms.
[0118] X 11 is preferably C 1-6 Alkylene group, -(CH 2 ) f1 -O-(CH 2 ) f2 - (wherein f1 is an integer of 0 to 6, for example, an integer of 1 to 6, and f2 is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH 2 ) f3 -Phenylene-(CH 2 ) f4 - (wherein f3 is an integer of 0 to 6, for example, an integer of 1 to 6, and f4 is an integer of 0 to 6, for example, an integer of 1 to 6). 1-6 The alkylene group may be linear or branched, but is 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.
[0119] X 11 More preferably, C 1-6An alkylene group or a phenylene group. 11 is C 1-6 In another embodiment, X is an alkylene group. 11 is a phenylene group.
[0120] X 13 is a single bond or a divalent group.
[0121] In one embodiment, X 13 is a single bond.
[0122] In one embodiment, X 13 is a divalent group.
[0123] X 13 The divalent group in is an alkylene, a phenylene, -CO-, -COO-, or -NR x1 -,-CONR x1 -,-OCONR x1 -, -NR x1 -CO-NR x1 -, -O-, -S-, -O-(CH 2 ) x1 -CONR x1 - and -O-(CH 2 ) x1 R may be a group containing at least one group selected from -CO-. x1 is a hydrogen atom or C 1-6 It is an alkyl group, and x1 is an integer of 1 to 20. The alkylene may preferably have 1 to 30 carbon atoms, more preferably 6 to 26 carbon atoms, for example, 8 to 24, 10 to 22, 12 to 20, 1 to 20, 1 to 10, or 1 to 6 carbon atoms.
[0124] X 13 is preferably C 1-30 Alkylene groups (e.g., C 1-12 Alkylene group, or C 1-6 alkylene group), -(CH 2 ) f5 -O-(CH 2 ) f6- (wherein f5 is an integer of 0 to 30, for example, an integer of 1 to 30, and f6 is an integer of 0 to 30, for example, an integer of 1 to 30), or -(CH 2 ) f7 -Phenylene-(CH 2 ) f8 - (wherein f7 is an integer of 0 to 30, for example, an integer of 1 to 30, and f8 is an integer of 0 to 30, for example, an integer of 1 to 30). 1-30 The alkylene group may be linear or branched, but is 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.
[0125] X 1 is preferably of the following formula: -X 11 -X 12 -X 13 - [In formula: X 11 is C 1-6 an alkylene group or a phenylene group, X 12 is -O-[(CH 2 ) nb O] nc - (In the formula, nb is an integer of 2 to 4, nc is an integer of 1 to 5, and z1 is 0 or 1.) is a group represented by X 13 is C 1-12 is an alkylene group. It is a group represented by the following formula:
[0126] R Si is a monovalent group containing a Si atom to which a hydroxyl group or a hydrolyzable group is bonded.
[0127] In a preferred embodiment, R Si 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’ -SiR 21’ p1’ R 22’ q1’ R 23’ r1’ and; R 22are 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, The sum of p1, q1 and r1 is 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, the sum of p1', q1' and r1' is 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, The sum of q1" and r1" is 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, The sum of k1, l1 and m1 is 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; The sum of p2, q2 and r2 is 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 R33’ 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, The sum of q2' and r2' is 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. The sum of k2, l2 and m2 is 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 e1l2 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:
[0128] In the above formula, R 11 are each independently a hydroxyl group or a hydrolyzable group.
[0129] R 11 are preferably each independently a hydrolyzable group.
[0130] 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.
[0131] 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.
[0132] R12 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.
[0133] 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.
[0134] 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.
[0135] 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 a straight chain or a branched chain, but is preferably a straight chain. 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.
[0136] In one embodiment, X 11 are each independently -C1-6 Alkylene-OC 1-6 Alkylene- or -OC 1-6 It is alkylene.
[0137] In a preferred embodiment, X 11 are 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.
[0138] 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.
[0139] 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.
[0140] 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.
[0141] 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.
[0142] In a preferred embodiment, R 15 is a single bond.
[0143] In the above formula, each t is independently an integer of 2 or more.
[0144] In a preferred embodiment, each t is independently an integer of 2 to 10, preferably an integer of 2 to 6.
[0145] In the above formula, R 14 each independently represents a hydrogen atom, a halogen atom, or -X 11 -SiR 11 n1 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.
[0146] 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.
[0147] 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).
[0148] R a1 are each independently -Z 1 -SiR 21p1 R 22 q1 R 23 r1 It is.
[0149] 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 )
[0150] In a preferred embodiment, Z 1 is a divalent organic group.
[0151] In a preferred embodiment, Z 1 is Z 1 Preferably, in formula (S3), (Si-Z) does not include a compound that forms a siloxane bond with the Si atom to which it is bonded. 1 --Si) does not contain a siloxane bond.
[0152] Z 1 is preferably C 1-30 Alkylene group, -(CH 2 ) z1 -O-(CH 2 ) 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 -(CH 2 ) z3 -Phenylene-(CH 2 ) 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). 1-30 The alkylene group may be linear or branched, but is preferably linear. These groups may contain, for example, fluorine atoms, C 1-6 Alkyl group, C 2-6 Alkenyl groups, and C 2-6It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.
[0153] In a preferred embodiment, Z 1 is C 1-30 Alkylene group or -(CH 2 ) z3 -Phenylene-(CH 2 ) z4 -, preferably -phenylene-(CH 2 ) z4 -It is.
[0154] In another preferred embodiment, Z 1 is C 1-30 Alkylene groups, such as C 1-6 Alkylene group or C 1-3 In one embodiment, Z is an alkylene group. 1 -CH 2 CH 2 CH 2 In another embodiment, Z 1 -CH 2 CH 2 In yet another embodiment, Z 1 -CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 --It could be.
[0155] R 21 are each independently -Z 1’ -SiR 21’ p1’ R 22’ q1’ R 23’ r1’ It is.
[0156] 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’ )
[0157] In a preferred embodiment, Z 1’ is a divalent organic group.
[0158] In a preferred embodiment, Z 1’ is Z 1’ Preferably, in formula (S3), (Si-Z) does not include a compound that forms a siloxane bond with the Si atom to which it is bonded. 1’ --Si) does not contain a siloxane bond.
[0159] Z 1’ is preferably C 1-30 Alkylene group, -(CH 2 ) z1’ -O-(CH 2 ) 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 -(CH 2 ) z3’ -Phenylene-(CH 2 ) 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). 1-30 The alkylene group may be linear or branched, but is 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.
[0160] In a preferred embodiment, Z 1’ is C 1-30 Alkylene group or -(CH 2 ) z3’ -Phenylene-(CH 2) z4’ -, preferably -phenylene-(CH 2 ) z4’ -It is.
[0161] In another preferred embodiment, Z 1’ is C 1-30 Alkylene groups, such as C 1-6 Alkylene group or C 1-3 In one embodiment, Z is an alkylene group. 1’ -CH 2 CH 2 CH 2 In another embodiment, Z 1’ -CH 2 CH 2 In yet another embodiment, Z 1’ is -CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 --It could be.
[0162] Above R 21’ are each independently -Z 1” -SiR 22” q1” R 23” r1” It is.
[0163] 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” )
[0164] In a preferred embodiment, Z 1” is a divalent organic group.
[0165] In a preferred embodiment, Z1” is Z 1” Preferably, in formula (S3), (Si-Z) does not include a compound that forms a siloxane bond with the Si atom to which it is bonded. 1” --Si) does not contain a siloxane bond.
[0166] Z 1” is preferably C 1-30 Alkylene group, -(CH 2 ) z1” -O-(CH 2 ) 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 -(CH 2 ) z3” -Phenylene-(CH 2 ) 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). 1-30 The alkylene group may be linear or branched, but is 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.
[0167] In a preferred embodiment, Z 1” is C 1-30 Alkylene group or -(CH 2 ) z3” -Phenylene-(CH 2 ) z4” -, preferably -phenylene-(CH 2 ) z4” -It is. 1” is such a group, light resistance, particularly ultraviolet resistance, can be improved.
[0168] In another preferred embodiment, Z 1” is C 1-30 Alkylene groups, such as C 1-6 Alkylene group or C1-3 In one embodiment, Z is an alkylene group. 1” -CH 2 CH 2 CH 2 In another embodiment, Z 1” -CH 2 CH 2 In yet another embodiment, Z 1” -CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 --It could be.
[0169] Above R 22” are each independently a hydroxyl group or a hydrolyzable group.
[0170] Above R 22” are preferably each independently a hydrolyzable group.
[0171] Above R 22” are preferably each independently -OR h , -OCOR h , -ON=CR h 2 , -NR h 2 , -NHR h or -NCO (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, Rh is an ethyl group.
[0172] R 23” are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.
[0173] 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.
[0174] Each q1″ is independently an integer of 0 to 3, and each r1″ is independently an integer of 0 to 3. The sum of q1″ and r1″ is not more than (SiR 22” q1” R 23” r1” ) units, it is 3.
[0175] 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.
[0176] R 22’ are each independently a hydroxyl group or a hydrolyzable group.
[0177] R 22’ are preferably each independently a hydrolyzable group.
[0178] R 22’ are preferably each independently -OR h , -OCOR h , -ON=CR h 2 , -NR h 2 , -NHR h or -NCO (wherein R h is a substituted or unsubstituted C 1-4alkyl 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.
[0179] R 23’ are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.
[0180] 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.
[0181] Each p1' is independently an integer of 0 to 3, each q1' is independently an integer of 0 to 3, and each r1' 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.
[0182] In one embodiment, p1' is 0.
[0183] 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.
[0184] 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.
[0185] 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.
[0186] R 22 are each independently a hydroxyl group or a hydrolyzable group.
[0187] R 22 are preferably each independently a hydrolyzable group.
[0188] R 22 are preferably each independently -OR h , -OCOR h , -ON=CR h 2 , -NR h 2 , -NHR h or -NCO (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, Rh is an ethyl group.
[0189] Above R 23 are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.
[0190] 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.
[0191] 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.
[0192] In one embodiment, p1 is 0.
[0193] 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.
[0194] 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.
[0195] In one embodiment, p1 is 0 and q1 is (SiR 21p1 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.
[0196] In the formula, R b1 are each independently a hydroxyl group or a hydrolyzable group.
[0197] R b1 are preferably each independently a hydrolyzable group.
[0198] R b1 are preferably each independently -OR h , -OCOR h , -ON=CR h 2 , -NR h 2 , -NHR h or -NCO (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.
[0199] In the formula, R c1 are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.
[0200] R c1 In the above, the monovalent organic group is preferably C 1-20 is an alkyl group, more preferably C 1-6It is preferably an alkyl group, more preferably a methyl group.
[0201] Each k1 is independently an integer of 0 to 3, each l1 is independently an integer of 0 to 3, and each m1 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.
[0202] In one embodiment, k1 is (SiR a1 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.
[0203] In formula (S3), there are at least two Si atoms having hydroxyl groups or hydrolyzable groups bonded thereto.
[0204] In a preferred embodiment, there are at least two Si atoms to which hydroxyl groups or hydrolyzable groups are bonded in the terminal portion of formula (S3).
[0205] In a preferred embodiment, the group represented by formula (S3) 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’ (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), or -Z 1” -SiR 22” q1” R23” 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.
[0206] In a preferred embodiment, in formula (S3), R 21’ 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.
[0207] In a preferred embodiment, in formula (S3), 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.
[0208] In a preferred embodiment, in formula (S3), 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.
[0209] In a preferred embodiment, in formula (S3), k1 is 2 or 3, preferably 3; p1 is 0; and q1 is 2 or 3, preferably 3.
[0210] R d1 are each independently -Z 2 -CR 31 p2 R 32 q2 R 33 r2 It is.
[0211] 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 )
[0212] In a preferred embodiment, Z 2 is a divalent organic group.
[0213] In a preferred embodiment, Z 2 does not contain a siloxane bond.
[0214] Z 2 is preferably C 1-30 Alkylene group, -(CH 2 ) z5 -O-(CH 2 ) 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 -(CH 2 ) z7 -Phenylene-(CH 2 ) 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). 1-30 The alkylene group may be linear or branched, but is 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.
[0215] In a preferred embodiment, Z 2 is C 1-30 Alkylene group or -(CH 2 ) z7 -Phenylene-(CH2 ) z8 -, preferably -phenylene-(CH 2 ) z8 -It is. 2 is such a group, light resistance, particularly ultraviolet resistance, can be improved.
[0216] In another preferred embodiment, the Z 2 is C 1-30 Alkylene groups, such as C 1-6 Alkylene group or C 1-3 In one embodiment, Z is an alkylene group. 2 -CH 2 CH 2 CH 2 In another embodiment, Z 2 -CH 2 CH 2 In yet another embodiment, Z 2 -CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 --It could be.
[0217] R 31 are each independently -Z 2’ -CR 32’ q2’ R 33’ r2’ It is.
[0218] 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’ )
[0219] In a preferred embodiment, Z 2’ does not contain a siloxane bond.
[0220] Z 2’ is preferably C 1-30 Alkylene group, -(CH 2 ) z5’ -O-(CH 2 ) 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 -(CH 2 ) z7’ -Phenylene-(CH 2 ) 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). 1-30 The alkylene group may be linear or branched, but is 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.
[0221] In a preferred embodiment, Z 2’ is C 1-30 Alkylene group or -(CH 2 ) z7’ -Phenylene-(CH 2 ) z8’ -, preferably -phenylene-(CH 2 ) z8’ -It is. 2’ is such a group, light resistance, particularly ultraviolet resistance, can be improved.
[0222] In another preferred embodiment, the Z 2’ is C 1-30 Alkylene groups, such as C 1-6 Alkylene group or C 1-3 In one embodiment, Z is an alkylene group. 2’ -CH 2 CH 2 CH 2 In another embodiment, Z2’ -CH 2 CH 2 In yet another embodiment, Z 2’ -CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 --It could be.
[0223] R 32’ are each independently -Z 3 -SiR 34 n2 R 35 3-n2 It is.
[0224] 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 )
[0225] In one embodiment, Z 3 is an oxygen atom.
[0226] In one embodiment, Z 3 is a divalent organic group.
[0227] In a preferred embodiment, Z 3 does not contain a siloxane bond.
[0228] Z 3 is preferably C 1-30 Alkylene group, -(CH 2 ) z5” -O-(CH 2 ) 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 -(CH 2 ) z7” -Phenylene-(CH 2 ) 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). 1-30 The alkylene group may be linear or branched, but is 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.
[0229] In a preferred embodiment, Z 3 is C 1-30 Alkylene group or -(CH 2 ) z7” -Phenylene-(CH 2 ) z8” -, preferably -phenylene-(CH 2 ) z8” -It is. 3 is such a group, light resistance, particularly ultraviolet resistance, can be improved.
[0230] In another preferred embodiment, the Z 3 is C 1-30 Alkylene groups, such as C 1-6 Alkylene group or C 1-3 In one embodiment, Z is an alkylene group. 3 -CH 2 CH 2 CH 2 In another embodiment, Z 3 -CH 2 CH 2 In yet another embodiment, Z 3 -CH 2 CH 2 CH 2 CH 2 CH2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 --It could be.
[0231] R 34 are each independently a hydroxyl group or a hydrolyzable group.
[0232] R 34 are preferably each independently a hydrolyzable group.
[0233] 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.
[0234] R 35 are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.
[0235] R 35 In the above, the monovalent organic group is preferably C 1-20 is an alkyl group, more preferably C 1-6It is preferably an alkyl group, more preferably a methyl group.
[0236] 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 (S4), 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 (S4).
[0237] 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.
[0238] 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.
[0239] 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.
[0240] In one embodiment, R 33’ is a hydroxyl group.
[0241] 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.
[0242] 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.
[0243] 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.
[0244] R 32 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.
[0245] 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.
[0246] 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.
[0247] In one embodiment, R 33 is a hydroxyl group.
[0248] 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.
[0249] Each p2 is independently an integer of 0 to 3, each q2 is independently an integer of 0 to 3, and each r2 is independently an integer of 0 to 3. The sum of p2, q2, and r2 is (CR 31 p2 R 32 q2 R 33 r2 ) units, it is 3.
[0250] In one embodiment, p2 is 0.
[0251] 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.
[0252] 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.
[0253] 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.
[0254] 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.
[0255] R f1 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.
[0256] 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.
[0257] In one embodiment, Rf1 is a hydroxyl group.
[0258] 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.
[0259] Each k2 is independently an integer of 0 to 3, each l2 is independently an integer of 0 to 3, and each m2 is 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.
[0260] 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.
[0261] In a preferred embodiment, in formula (S4), 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.
[0262] In a preferred embodiment, in formula (S4), 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.
[0263] In a preferred embodiment, in formula (S4), R e1 When present, at least one, and preferably all, Ra1 In the above formula, n2 is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.
[0264] In a preferred embodiment, in formula (S4), k2 is 0, l2 is 2 or 3, preferably 3, and n2 is 2 or 3, preferably 3.
[0265] R g1 and R h1 are each independently -Z 4 -SiR 11 n1 R 12 3-n1 , -Z 4 -SiR a1 k1 R b1 l1 R c1 m1 , -Z 4 -CR d1 k2 R e1 l2 R f1 m2 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.
[0266] In a preferred embodiment, R g1 and R h1 are each independently -Z 4 -SiR 11 n1 R 12 3-n1 It is.
[0267] 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 123-n1 )
[0268] In one embodiment, Z 4 is an oxygen atom.
[0269] In one embodiment, Z 4 is a divalent organic group.
[0270] In a preferred embodiment, Z 4 does not contain a siloxane bond.
[0271] Z 4 is preferably C 1-30 Alkylene group, -(CH 2 ) z5” -O-(CH 2 ) 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 -(CH 2 ) z7” -Phenylene-(CH 2 ) 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). 1-30 The alkylene group may be linear or branched, but is 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.
[0272] In a preferred embodiment, Z 4 is C 1-30 Alkylene group or -(CH 2 ) z7” -Phenylene-(CH 2 ) z8” -, preferably -phenylene-(CH 2 ) z8” -It is. 3is such a group, light resistance, particularly ultraviolet resistance, can be improved.
[0273] In another preferred embodiment, the Z 4 is C 1-30 Alkylene groups, such as C 1-6 Alkylene group or C 1-3 In one embodiment, Z is an alkylene group. 4 -CH 2 CH 2 CH 2 In another embodiment, Z 4 -CH 2 CH 2 In yet another embodiment, Z 4 -CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 --It could be.
[0274] In one embodiment, formulas (S1), (S2), (S3), and (S4) do not contain a siloxane bond.
[0275] In one embodiment, R Si is a group represented by formula (S2), (S3), (S4), or (S5).
[0276] In one embodiment, R Si is a group represented by formula (S2), (S3), or (S4).
[0277] In one embodiment, R Si is a group represented by formula (S3), (S4) or (S5).
[0278] In one embodiment, R Si is a group represented by formula (S3) or (S4).
[0279] In one embodiment, R Si is a group represented by formula (S4) or (S5).
[0280] In one embodiment, R Si is a group represented by formula (S1). In a preferred embodiment, formula (S1) is a group represented by formula (S1-b). In a preferred embodiment, 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 occurrence 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.
[0281] In one embodiment, R Si 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.
[0282] In one embodiment, R Si is a group represented by formula (S3). In a preferred embodiment, formula (S2) is -SiR a1 2 R c1 , or -SiR a1 3 and R a1 -Z 1 -SiR 22 q1 R 23 r1 and Z 1 is C 1-6 Alkylene group, -(CH 2 ) z1 -O-(CH 2 ) 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 -(CH 2 ) z3 -Phenylene-(CH 2 )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.
[0283] In one embodiment, R Si is a group represented by formula (S4). In a preferred embodiment, formula (S3) is -CR e1 2 R f1 , or -CR e1 3 and R e1 -Z 3 -SiR 34 n2 R 35 3-n2 and Z 3 is C 1-6 Alkylene group, -(CH 2 ) z5” -O-(CH 2 ) 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 -(CH 2 ) z7” -Phenylene-(CH 2 ) 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.
[0284] In one embodiment, R Si 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, -(CH 2 ) z5”-O-(CH 2 ) 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 -(CH 2 ) z7” -Phenylene-(CH 2 ) 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.
[0285] In a preferred embodiment, formula (S2) is the following formula: 1 Represents the connection point with. TIFF2025062586000018.tif2159
[0286] In a preferred embodiment, formula (S3) is the following formula: 1 Represents the connection point with. TIFF2025062586000019.tif194142
[0287] In a preferred embodiment, formula (S4) is the following formula: 1 Represents the connection point with. TIFF2025062586000020.tif162138
[0288] In a preferred embodiment, formula (S5) is the following formula: 1 Represents the connection point with. TIFF2025062586000021.tif25134
[0289] In a preferred embodiment, the compound of the present disclosure comprises R S is expressed by the following formula: R 1 -[Si(CH 3 ) 2 -O] x -Si(CH3 ) 2 - [In the formula, R 1 is an alkyl group having 1 to 6 carbon atoms or R 1a na R 1b 3-na Si-(O) z - and R 1a is (CH 3 ) 3 SiO-, R 1b is an alkyl group having 1 to 4 carbon atoms, na is 2 or 3; and x is an integer from 5 to 50. is a group represented by X 1 is expressed by the following formula: -X 11 -X 12 -X 13 - [In formula: X 11 is C 1-6 an alkylene group or a phenylene group, X 12 is -O-[(CH 2 ) nb O] nc - (In the formula, nb is an integer of 2 to 4, nc is an integer of 1 to 5, and z1 is 0 or 1.) is a group represented by X 13 is C 1-12 is an alkylene group. is a group represented by R Si is expressed by the following formula: -SiR 11 3 [In the formula, R 11 -OR h and R h is an alkyl group having 1 to 4 carbon atoms.] is a group represented by α is 1, It is a compound represented by formula (1).
[0290] In one embodiment, suitable silane compounds of the present disclosure include, but are not limited to, the following compounds:
[0291] In the following formula, n is preferably 0 or more, more preferably 3 or more, and particularly preferably 6 or more. Moreover, n is preferably 500 or less, more preferably 300 or less, and particularly preferably 200 or less. Furthermore, n is preferably 3 or more and 300 or less, more preferably 3 or more and 200 or less, particularly preferably 3 or more and 100 or less, and most preferably 10 or more and 30 or less. p is preferably 1 or more. Furthermore, p is preferably 50 or less, more preferably 30 or less, and particularly preferably 10 or less. p is preferably 1 or more and 50 or less, more preferably 1 or more and 30 or less, and particularly preferably 1 or more and 10 or less. q is preferably 1 or more, and more preferably 2 or more. Furthermore, q is preferably 80 or less, more preferably 60 or less, and particularly preferably 50 or less. q is preferably 1 or more and 80 or less, more preferably 1 or more and 60 or less, and particularly preferably 1 or more and 50 or less. Ph represents a phenylene group.
[0292] CH 3 [Si(CH 3 ) 2 O] n Si(CH 3 ) 2 CH 2 CH 2 CH 2 O(CH 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3 CH 3 CH 2 CH 2 CH 2 [Si(CH 3 ) 2 O] n Si(CH 3 ) 2 CH 2 CH 2 CH 2 O(CH 2 CH2 O)p(CH 2 ) q Si(OCH 3 ) 3 [(CH 3)3 SiO] 3 SiO[Si(CH 3 ) 2 O] n Si(CH 3 ) 2 CH 2 CH 2 CH 2 O(CH 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3 [(CH 3)3 SiO] 2 (CH 3) SiO[Si(CH 3 ) 2 O] n Si(CH 3 ) 2 CH 2 CH 2 CH 2 O(CH 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3
[0293] CH 3 [Si(CH 3 ) 2 O] n Si(CH 3 ) 2 CH 2 CH 2 CH 2 O(CH 2 CH 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3 CH 3 CH 2 CH 2 CH2 [Si(CH 3 ) 2 O] n Si(CH 3 ) 2 CH 2 CH 2 CH 2 O(CH 2 CH 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3 [(CH 3)3 SiO] 3 SiO[Si(CH 3 ) 2 O] n Si(CH 3 ) 2 CH 2 CH 2 CH 2 O(CH 2 CH 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3 [(CH 3)3 SiO] 2 (CH 3) SiO[Si(CH 3 ) 2 O] n Si(CH 3 ) 2 CH 2 CH 2 CH 2 O(CH 2 CH 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3
[0294] CH 3 [Si(CH 3 ) 2 O] n Si(CH 3 ) 2 CH 2 CH2 CH 2 O(CH 2 CH 2 CH 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3 CH 3 CH 2 CH 2 CH 2 [Si(CH 3 ) 2 O] n Si(CH 3 ) 2 CH 2 CH 2 CH 2 O(CH 2 CH 2 CH 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3 [(CH 3)3 SiO] 3 SiO[Si(CH 3 ) 2 O] n Si(CH 3 ) 2 CH 2 CH 2 CH 2 O(CH 2 CH 2 CH 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3 [(CH 3)3 SiO] 2 (CH 3) SiO[Si(CH 3 ) 2 O] n Si(CH 3 ) 2 CH 2 CH 2 CH 2 O(CH 2 CH2 CH 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3
[0295] CH 3 [Si(CH 3 ) 2 O] n Si(CH 3 ) 2 Phosphorus 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3 CH 3 CH 2 CH 2 CH 2 [Si(CH 3 ) 2 O] n Si(CH 3 ) 2 Phosphorus 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3 [(CH 3)3 SiO] 3 SiO[Si(CH 3 ) 2 O] n Si(CH 3 ) 2 Phosphorus 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3 [(CH 3)3 SiO] 2 (CH 3) SiO[Si(CH 3 ) 2 O] n Si(CH 3 ) 2 Phosphorus 2 CH2 O)p(CH 2 ) q Si(OCH 3 ) 3
[0296] CH 3 [Si(CH 3 ) 2 O] n Si(CH 3 ) 2 Phosphorus 2 CH 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3 CH 3 CH 2 CH 2 CH 2 [Si(CH 3 ) 2 O] n Si(CH 3 ) 2 Phosphorus 2 CH 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3 [(CH 3)3 SiO] 3 SiO[Si(CH 3 ) 2 O] n Si(CH 3 ) 2 Phosphorus 2 CH 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3 [(CH 3)3 SiO] 2 (CH 3) SiO[Si(CH 3 ) 2 O] n Si(CH 3 ) 2 Phosphorus2 CH 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3
[0297] CH 3 [Si(CH 3 ) 2 O] n Si(CH 3 ) 2 Phosphorus 2 CH 2 CH 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3 CH 3 CH 2 CH 2 CH 2 [Si(CH 3 ) 2 O] n Si(CH 3 ) 2 Phosphorus 2 CH 2 CH 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3 [(CH 3)3 SiO] 3 SiO[Si(CH 3 ) 2 O] n Si(CH 3 ) 2 Phosphorus 2 CH 2 CH 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3 [(CH 3)3 SiO] 2 (CH 3) SiO[Si(CH 3 )2 O] n Si(CH 3 ) 2 PhO(CH 2 CH 2 CH 2 CH 2 O)p(CH 2 ) q Si(OCH 3 ) 3
[0298] Specific examples of the compounds of the present disclosure include the following compounds: CH 3 CH 2 CH 2 CH 2 [Si(CH 3 ) 2 ] n Si(CH 3 ) 2 CH 2 CH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 CH 2 Si(OCH 3 ) 3 [(CH 3)3 SiO] 2 (CH 3) SiO[Si(CH 3 ) 2 O] n Si(CH 3 ) 2 PhO(CH 2 CH 2 O) 5 (CH 2 ) 11 Si(OCH 3 ) 3
[0299] [Manufacturing method] A method for producing the silane compound of the present disclosure will be described below. Note that the method for producing the silane compound of the present disclosure is not limited to the following method.
[0300] (Manufacturing method 1) In this production method, an olefin compound having a halogen atom at its terminal is reacted with a carbinol to produce an olefin compound containing one or more Si atoms to which no hydroxyl group or hydrolyzable group is directly bonded, and the olefin group of this aromatic compound is converted into a compound represented by, for example, the following formula: HSiR j27 m3 R j28 3-m3 [In the formula, R j27 are each independently a hydroxyl group or a hydrolyzable group, R j28 are each independently a monovalent organic group, m3 is 1 to 3. A silane compound can be obtained by reacting the silane compound with a compound represented by the following formula: The monovalent organic group does not contain a hydrolyzable group.
[0301] Examples of carbinols include carbinols having one or more Si atoms that are not directly bonded to a hydroxyl group or hydrolyzable group. Examples of carbinols having one or more Si atoms that are not directly bonded to a hydroxyl group or hydrolyzable group include compounds having a hydroxyl group at one end of polydimethylsiloxane (e.g., Silaplane (trademark) FM-0411, Silaplane (trademark) FM-0421, Silaplane (trademark) FM-0425, Silaplane (trademark) FM-DA11, Silaplane (trademark) FM-DA21, and Silaplane (trademark) FM-DA26, all of which are manufactured by JNC Corporation).
[0302] Examples of the olefin compound having a halogen atom at the end include the compound represented by formula (1b): Hal-R X1 -CH=CH 2 (1b) [In formula: Hal is a halogen, such as fluorine, chlorine, bromine, or iodine, preferably bromine; R X1 is a single bond or a divalent group. Examples of the compound include compounds represented by the following formula:
[0303] As the above formula (1b), for example, The following formula (1b1), (1b2), (1b3), or (1b4): Hal-R X -CONR 81 -(CH 2 ) za -CH=CH 2 (1b1) Hal-R X -CON[-(CH 2 ) za -CH=CH 2 ] 2 (1b2) Hal-R X -CONR 81 -(CH 2 ) zb -CR 82 [-(CH 2 ) za -CH=CH 2 ] 2 (1b3) Hal-R X -CONR 81 -(CH 2 ) zb -C[-(CH 2 ) za -CH=CH 2 ] 3 (1b4) [In formula: Hal is a halogen, R X is a single bond or a divalent group, R 81 is a hydrogen atom or a monovalent organic group, R 82 is a hydrogen atom or a monovalent organic group, za is an integer from 0 to 30, zb is an integer from 0 to 30. or Formula (1d1), (1d2), or (1d3): Hal-R X -(CH 2 ) za -CH=CH 2 (1d1) Hal-R X -SiR 83 [-(CH 2 ) za -CH=CH 2 ] 2 (1d2) Hal-R X -Si[-(CH 2 ) za -CH=CH 2 ] 3 (1d3) [In formula: Hal is a halogen, R X is a single bond or a divalent group, R 83 is a hydrogen atom or a monovalent organic group, za is an integer from 0 to 30. Examples of the compound include compounds represented by the following formula:
[0304] In one embodiment, the olefin compound having a halogen atom at the end includes allyl bromide, 4-bromo-1-butene, 5-bromo-1-pentene, 6-bromo-1-hexene, 7-bromo-1-heptene, 8-bromo-1-octene, 9-bromo-1-nonene, 10-bromo-1-decene, 11-bromo-1-undecene, 12-bromo-1-dodecene, 13-bromo-1-tridecene, 14-bromo-1-tetradecene, 15-bromo-1-pentadecene, 16-bromo-1-hexadecene, 17-bromo-1-heptadecene, and 18-bromo-1-pentadecene. decene, 18-bromo-1-octadecene, 19-bromo-1-nonadecene, 20-bromo-1-icosene, 21-bromo-1-henicosene, 24-bromo-1-tetracosene, 30-bromo-1-triacontene, allyl chloride, 4-chloro-1-butene, 5-chloro-1-pentene, 6-chloro-1-hexene, 7-chloro-1-heptene, 8-chloro-1-octene, 9-chloro-1-nonene, 10-chloro-1-decene, 11-chloro-1-undecene, 12-chloro-1-dodecene, 13-chloro-1-tridecene, 14-chloro-1-triphenylphosphine, 15-chloro-1-triphenylphosphine, 16-chloro-1-triphenylphosphine, 17-chloro-1-pentene, 18-chloro-1-triphenylphosphine, 19-chloro-1-triphenylphosphine, 20-bromo-1-octene, 21-bromo-1-hexene, 22-bromo-1-hexene, 23-bromo-1-triphenylphosphine, 24-bromo-1-tetradecene, 25-bromo-1-triphenylphosphine, 26-bromo-1-triphenylphosphine, 27-bromo-1-triphenylphosphine, 28-bromo-1-triphenylphosphine, 29-bromo-1-triphenylphosphine, 30-bromo-1-triphenylphosphine, 31-bromo-1-triphenylphosphine, 32-bromo-1-triphenylphosphine, 33-bromo-1-triphenylphosphine, 34-bromo-1-triphenylphosphine, 35-bromo-1-triphenylphosphine Decene, 14-chloro-1-tetradecene, 15-chloro-1-pentadecene, 16-chloro-1-hexadecene, 17-chloro-1-heptadecene, 18-chloro-1-octadecene, 19-chloro-1-nonadecene, 20-chloro-1-icosene, 21-chloro-1-henicosene, 24-chloro-1-tetracosene, 30-chloro-1-triacontene, allyl iodide, 4-iodo-1-butene, 5-iodo-1-pentene, 6-iodo-1-hexene, 7-iodo-1-heptene, 8-iodo-1-octene, 9- Examples of the iodo-1-nonene include 10-iodo-1-decene, 11-iodo-1-undecene, 12-iodo-1-dodecene, 13-iodo-1-tridecene, 14-iodo-1-tetradecene, 15-iodo-1-pentadecene, 16-iodo-1-hexadecene, 17-iodo-1-heptadecene, 18-iodo-1-octadecene, 19-iodo-1-nonadecene, 20-iodo-1-icosene, 21-iodo-1-henicosene, 24-iodo-1-tetracosene, and 30-iodo-1-triacontene.
[0305] The reaction between a one-terminated carbinol containing one or more silicon atoms to which a hydroxyl group or hydrolyzable group is not directly bonded and an olefin compound having a halogen at the end is carried out in the presence of a base. Either an organic base or an inorganic base can be used as the base. Organic bases include triethylamine, diisopropylethylamine, diethylamine, etc. Inorganic bases include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc.
[0306] The reaction can be carried out in an organic solvent, without particular limitation, so long as the organic solvent does not react with the base.
[0307] In one embodiment, 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; glycol ethers such as dipropylene glycol dimethyl ether; cyclic ethers such as tetrahydrofuran, tetrahydropyran, and dioxane; ethers such as diethyl ether and cyclopentyl methyl ether; siloxanes such as hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, octamethylcyclotetrasiloxane, octamethylcyclopentasiloxane, decamethylcyclopentasiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, and tetradecamethylhexasiloxane; or a mixed solvent of two or more of these.
[0308] (Manufacturing method 2) In this production method, an aromatic compound having a siloxane group and an olefin-containing group is produced by reacting an aromatic compound having a halogen atom and a terminal olefin-containing group with a silane compound, and the olefin group of this aromatic compound is converted into a siloxane group represented by, for example, the following formula: HSiR j27 m3 R j28 3-m3 [In the formula, R j27 are each independently a hydroxyl group or a hydrolyzable group, R j28 are each independently a monovalent organic group, m3 is 1 to 3. A silane compound can be obtained by reacting the silane compound with a compound represented by the following formula: The monovalent organic group does not contain a hydrolyzable group.
[0309] Examples of aromatic compounds having a halogen atom and a terminal olefin-containing group include those represented by the formula (1b): Hal-R Ar -R X1 -CH=CH 2 (1b) [In formula: Hal is a halogen, such as fluorine, chlorine, bromine, or iodine, preferably bromine; R Ar is a divalent aromatic group, and has the same meaning as defined in formula (1), R X1 is a divalent to decavalent group containing two or more ether bonds. Examples of the compound include compounds represented by the following formula:
[0310] As the above formula (1b), for example, The following formula (1b1), (1b2), (1b3), or (1b4): Hal-R Ar -R X -CONR 81 -(CH 2 ) za -CH=CH 2 (1b1) Hal-R Ar -R X -CON[-(CH 2 ) za -CH=CH 2 ] 2 (1b2) Hal-R Ar -R X -CONR 81 -(CH 2 ) zb -CR 82[-(CH 2 ) za -CH=CH 2 ] 2 (1b3) Hal-R Ar -R X -CONR 81 -(CH 2 ) zb -C[-(CH 2 ) za -CH=CH 2 ] 3 (1b4) [In formula: Hal is a halogen, R Ar is a divalent aromatic group, R X is a divalent group containing two or more ether bonds, R 81 is a hydrogen atom or a monovalent organic group, R 82 is a hydrogen atom or a monovalent organic group, za is an integer from 0 to 30, zb is an integer from 0 to 30. or Formula (1d1), (1d2), or (1d3): Hal-R Ar -R X -(CH 2 ) za -CH=CH 2 (1d1) Hal-R Ar -R X -SiR 83 [-(CH 2 ) za -CH=CH 2 ] 2 (1d2) Hal-R Ar -R X -Si[-(CH 2 ) za -CH=CH 2 ] 3 (1d3) [In formula: Hal is a halogen, R Aris a divalent aromatic group, R X is a divalent group containing two or more ether bonds, R 83 is a hydrogen atom or a monovalent organic group, za is an integer from 0 to 30. Examples of the compound include compounds represented by the following formula:
[0311] The compound represented by the above formula (1b1), (1b2), (1b3), or (1b4), or the compound represented by the formula (1d1), (1d2), or (1d3), is reacted with a silane compound to obtain, respectively: The following formula (1a1), (1a2), (1a3), or (1a4): R A -R S -SiR 6 2 -R Ar -R X -CONR 81 -(CH 2 ) za -CH=CH 2 (1a1) R A -R S -SiR 6 2 -R Ar -R X -CON[-(CH 2 ) za -CH=CH 2 ] 2 (1a2) R A -R S -SiR 6 2 -R Ar -R X -CONR 81 -(CH 2 ) zb -CR 82 [-(CH 2 ) za -CH=CH 2 ] 2 (1a3) R A -R S -SiR 6 2-R Ar -R X -CONR 81 -(CH 2 ) zb -C[-(CH 2 ) za -CH=CH 2 ] 3 (1a4) or (1c1), (1c2), or (1c3) below: R A -R S -SiR 6 2 -R Ar -R X -(CH 2 ) za -CH=CH 2 (1c1) R A -R S -SiR 6 2 -R Ar -R X -SiR 83 [-(CH 2 ) za -CH=CH 2 ] 2 (1c2) R A -R S -SiR 6 2 -R Ar -R X -Si[-(CH 2 ) za -CH=CH 2 ] 3 (1c3) [In formula: R A is a hydrocarbon group, or a monovalent group containing one or more Si atoms to which a hydroxyl group or a hydrolyzable group is not directly bonded, R S is expressed by the following formula: [ka] (In the formula: R 73 are each independently a single bond, C 1-12 Alkylene group, -R 76-OR 76 -, -R 78 -R 77 -R 78 -, -R 78 -R 77 -R 79 -R 77 -R 78 -, -R 78 -R 77 -R 79 -R 76 -R 79 -R 77 -R 78 - or -R 79 -R 76 -R 79 -R 77 -R 79 -R 76 -R 79 - and R 74 are each independently 1-12 Alkylene group, -R 76 -OR 76 -, -R 78 -R 77 -R 78 -, -R 78 -R 77 -R 79 -R 77 -R 78 -, -R 78 -R 77 -R 79 -R 76 -R 79 -R 77 -R 78 - or -R 79 -R 76 -R 79 -R 77 -R 79 -R 76 -R 79 - and R 76 are each independently 1-6 is an alkylene group, R 77 each independently represents an optionally substituted phenylene group or naphthylene group, R 78 each independently represents a single bond or C 1-6 is an alkylene group, R 79 are each independently a single bond or an oxygen atom; R 75 are each independently a hydrocarbon group; x is an integer from 0 to 500; y is an integer from 0 to 500; z is an integer from 0 to 500; x+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 6 are each independently a hydrocarbon group; R Ar is a divalent aromatic group, R X is a divalent group containing two or more ether bonds, R 81 is a hydrogen atom or a monovalent organic group, R 83 is a hydrogen atom or a monovalent organic group, za is an integer from 0 to 30, zb is an integer from 0 to 30. A compound represented by the formula:
[0312] In formulae (1a1) to (1a4), (1b1) to (1b4), (1c1) to (1c3), and (1d1) to (1d3), R A , R S , R 6 , and R Ar is R in formula (1). A , R S , R 6 , and R Ar and may have a similar aspect.
[0313] In formulae (1b1) to (1b4) and (1d1) to (1d3), Hal is a halogen, specifically a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, preferably a chlorine atom or a bromine atom, more preferably a bromine atom.
[0314] In formulae (1a1) to (1a4), (1b1) to (1b4), (1c1) to (1c3), and (1d1) to (1d3), R X is a divalent group containing two or more ether bonds.
[0315] In one embodiment, the divalent group has the formula: -X 11’ -X 12’ -X 13’ - [In formula: X 11’ is a single bond or a divalent group, X 12’ is -(O) z1 -[(CH 2 ) nb O] nc - (wherein nb is an integer of 1 to 10, nc is an integer of 1 to 30, and z1 is 0 or 1), X 13’ is a single bond or a divalent group. X may be a group represented by the formula: 11’ , X 12’ , and X 13’ is X in formula (1). 11 , X 12 , and X 13 and may have a similar aspect.
[0316] R 81 is a hydrogen atom or a monovalent organic group.
[0317] R 82 is a hydrogen atom, a hydroxyl group, or a monovalent organic group.
[0318] R 83 is a hydrogen atom, a hydroxyl group, or a monovalent organic group.
[0319] R 81 , R 82 and R 83Each monovalent organic group in the formula (I) may independently be a hydrocarbon group or a hydrocarbon group having an oxygen atom at the end or in the main chain.
[0320] The monovalent organic group is preferably C 1-20 Alkyl group, or -(C s H 2s ) t1 -(OC s H 2s ) t2 H (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.
[0321] In formulas (1a1) to (1a4), (1b1) to (1b4), (1c1) to (1c3), and (1d1) to (1d3), za is an integer of 0 to 30.
[0322] In one embodiment, za is 0.
[0323] In another embodiment, za is an integer from 1 to 30, for example, an integer from 4 to 30, 8 to 28, 10 to 26, or 14 to 22.
[0324] In formulas (1a1) to (1a4), (1b1) to (1b4), (1c1) to (1c3) and (1d1) to (1d3), zb is an integer of 0 to 30.
[0325] In one embodiment, zb is 0.
[0326] In another embodiment, zb is an integer of 1 to 30, for example, an integer of 4 to 30, 8 to 28, 10 to 26, or 14 to 22.
[0327] Examples of the silane compound include the following compounds. ClSiR 85 3 , ClSiR 85 (SiR 85 3 ) 2 , [In the formula, R 85 are each independently a hydrocarbon group, preferably C 1-6 Alkyl groups, more preferably C 1-3 An alkyl group is preferable, and a methyl group is more preferable.] [ka] [In the formula, n is 0 to 500, preferably 0 to 200 (in one embodiment, n is 0, in another embodiment, n is 1 to 200, preferably 10 to 100, more preferably 10 to 50, and in yet another embodiment, n is preferably 1 to 10, more preferably 1 to 6).
[0328] The silane compound may be cyclic siloxane.The cyclic siloxane may be, for example, hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, tetradecamethylcycloheptasiloxane, hexadecamethylcyclooctasiloxane, octadecamethylcyclononasiloxane, eicosamethylcyclodecasiloxane, etc.From the viewpoint of reactivity, hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane are preferred, and hexamethylcyclotrisiloxane and octamethylcyclotetrasiloxane are more preferred.
[0329] By reacting with the cyclic siloxane and then reacting with a capping agent, a silane compound represented by (1a1), (1a2), (1a3), or (1a4), or (1c1), (1c2), or (1c3) can be obtained. Chlorosilanes can be used as capping agents. Specific examples of chlorosilanes include chlorotrimethylsilane, chlorotriethylsilane, chlorotripropylsilane, chlorotributylsilane, chlorocyclohexyldimethylsilane, chlorodimethylphenylsilane, chloromethyldiphenylsilane, chlorotriphenylsilane, and chlorosilanes represented by the following formulas. [ka]
[0330] The present disclosure provides intermediates for use in the preparation of the silane compounds of the present disclosure. The intermediate compounds of the present disclosure have the formula: R S -X 1a -CH=CH 2 [In formula: R S is a monovalent group containing one or more Si atoms to which a hydroxyl group or a hydrolyzable group is not directly bonded, X 1a is a divalent group containing two or more ether bonds. The compound may be represented by the formula:
[0331] In a preferred embodiment, the intermediate of the compound of the present disclosure has the formula: R S -X 1a -CONR 51 -(CH 2 ) x -CH=CH 2 [In formula: R S is a monovalent group containing one or more Si atoms to which a hydroxyl group or a hydrolyzable group is not directly bonded, X 1a is a divalent group containing two or more ether bonds, R 51is a hydrogen atom or a monovalent hydrocarbon group, x is an integer from 0 to 30. The compound may be represented by the formula:
[0332] Next, the surface treatment agent of the present invention will be described.
[0333] The surface treatment agent of the present disclosure contains at least one silane compound represented by formula (1). That is, the surface treatment agent of the present disclosure may contain two silane compounds represented by formula (1).
[0334] The silane compound represented by formula (1) may include a silane compound having one Si atom bonded to a hydrolyzable group, and a silane compound having two or more, for example, two or three, Si atoms bonded to water-decomposable groups.
[0335] The ratio by mass of the silane compound having one Si atom bonded to a hydrolyzable group and the silane compound having two or more Si atoms bonded to water-decomposable groups can be 10:90 to 90:10, preferably 20:80 to 80:20, for example, 30 to 70 to 70:30.
[0336] In one embodiment, the surface treatment agent of the present disclosure is at least one compound represented by formula (1) itself.
[0337] In one embodiment, the content of the compound represented by the above formula (1) may be preferably 0.1 to 50.0 mass%, more preferably 1.0 to 30.0 mass%, further 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.
[0338] In another embodiment, the content of the compound represented by the above formula (1) 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.
[0339] In one embodiment, the surface treatment agent of the present disclosure may contain a compound represented by formula (1) and a condensate in which at least a portion of the compound represented by formula (1) is condensed.
[0340] In the above embodiment, the content of the condensate may be preferably 40% by mass or less, more preferably 30% by mass or less, based on the total of the compound represented by formula (1) and the condensate. Here, the content of the condensate can be determined, for example, from the abundance ratio of peak position and area in GPC (gel permeation chromatography).
[0341] The surface treatment agent of the present disclosure may further comprise a compound represented by formula (3): R 51 -R 52 -CONR 54 -R 53 -SiR 11 n1 R 12 3-n1 (3) [In formula: R 51 is CH 3 CH 2 CH 2 -, CH 3 CH=CH- or R 12 3-n1 R 11 n1 Si-, R 52 is C 0-30 is an alkylene group, R 53 is C 1-10 is an alkylene group, R 54 is a hydrogen atom, C 1-6 an alkyl group or a phenyl group, R 11 are each independently a hydroxyl group or a hydrolyzable group, R 12 each independently represents a hydrogen atom or a monovalent organic group, n1 is an integer from 1 to 3. The surface treatment agent of the present disclosure may contain a compound represented by formula (3), thereby further improving the friction durability.
[0342] In one embodiment, R 51 is CH 3 CH 2 CH 2 - and CH 3 It can be CH=CH-.
[0343] In one embodiment, R 52 is C 0 An alkylene group, i.e., a single bond.
[0344] In another embodiment, R 52 is C 1-30 Alkylene groups, such as C 1-10 Alkylene group, C 3-6 Alkylene group, C 6-27 Alkylene group, C 7-23 Alkylene group, C 8-21 Alkylene group, C 9-19 It may be an alkylene group.
[0345] R 53 is C 1-10 Alkylene group, preferably C 2-6 Alkylene group, more preferably C 2-4 an alkylene group,
[0346] In one embodiment, R 54 is a hydrogen atom.
[0347] In another embodiment, R 54 is C 1-6 It is an alkyl group or a phenyl group.
[0348] R 54 C in 1-6 The alkyl group may be linear or branched. 1-6 The alkyl group is linear. 1-6 The alkyl group is branched.1-6 The alkyl group is preferably C 1-4 It is an alkyl group.
[0349] R 11 , R 12 and n are defined as in formula (1).
[0350] The surface treatment agent according to the present disclosure may contain the compound represented by formula (3) in an amount of preferably 0.1% by mass to 30% by mass, more preferably 0.5% by mass to 20% by mass, and even more preferably 1.0% by mass to 20% by mass, based on the total amount of the compound represented by formula (1) and the compound represented by formula (3).
[0351] In one embodiment, the surface treatment agent of the present disclosure is R 54 C 1-6 The compound represented by formula (3), which is an alkyl group or a phenyl group, may be contained in an amount of, for example, 0.5% by mass to 99.5% by mass, preferably 0.5% by mass to 30% by mass, more preferably 1.0% by mass to 20% by mass, or 30% by mass to 70% by mass, or 70% by mass to 99.5% by mass, based on the total of the compound represented by formula (1) and the compound represented by formula (3).
[0352] In one embodiment, the surface treatment agent of the present disclosure is R 54 R 12 3-n1 R 11 n1 The compound represented by formula (3) which is Si- may be contained in an amount of, for example, 0.1 mass% to 99.5 mass%, preferably 0.1 mass% to 3.0 mass%, more preferably 0.1 mass% to 1.0 mass%, or alternatively 3.0 mass% to 50 mass%, 50 mass% to 99.5 mass%, 30 mass% to 70 mass%, or 70 mass% to 99.5 mass%, relative to the total of the compound represented by formula (1) and the compound represented by formula (3).
[0353] The composition 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.
[0354] In one embodiment, the surface treatment agent of the present disclosure is R 90 This includes compounds represented by -OH. R 90 is a monovalent organic group, preferably C 1-20 Alkyl group or C 3-20 These groups are alkylene groups, and may be substituted with one or more substituents. Examples of the substituents include a hydroxyl group, -OR 91 (where R 91 is C 1-10 Alkyl groups, preferably C 1-3 Alkyl groups, for example methyl groups, can be mentioned.
[0355] In one embodiment, the surface treatment agent of the present disclosure is R 81 OR 82 , R 83 n8 C 6 H 6-n8 , R 84 R 85 R 86 Si-(O-SiR 87 R 88 ) m8 -R 89 , and (OSiR 87 R 88 ) m9 [In the ceremony R 81 ~R 89 are each independently a monovalent organic group having 1 to 10 carbon atoms, m8 is an integer from 1 to 6, m9 is an integer from 3 to 8; n8 is an integer from 0 to 6. The solvent may include a solvent selected from compounds represented by the formula:
[0356] The monovalent organic group having 1 to 10 carbon atoms may be a straight chain or a branched chain, and may further contain a cyclic structure.
[0357] In one embodiment, the monovalent organic group having 1 to 10 carbon atoms may contain an oxygen atom, a nitrogen atom, or a halogen atom.
[0358] In another embodiment, the monovalent organic group having 1 to 10 carbon atoms does not contain a halogen atom.
[0359] In a preferred embodiment, the monovalent organic group having 1 to 10 carbon atoms is a hydrocarbon group which may be substituted with a halogen, and preferably a hydrocarbon group which is not substituted with a halogen.
[0360] In one embodiment, the hydrocarbon group is linear.
[0361] In another embodiment, the hydrocarbon group is branched.
[0362] In another embodiment, the hydrocarbon group comprises a cyclic structure.
[0363] In one embodiment, the solvent is R 81 OR 82 It is.
[0364] R 81 and R 82 are each independently preferably a hydrocarbon group having 1 to 8 carbon atoms, more preferably C 1-6 or C 5-8 It may be a cycloalkyl group of the formula:
[0365] In one embodiment, the solvent is R 83 n8 C 6 H 6-n8 It is.
[0366] C 6 H 6-n8 is an n8-valent benzene ring. That is, R 83 n8 C 6 H 6-n8 is n8 R 83 is benzene substituted with
[0367] R 83each independently represents a halogen or a C optionally substituted by a halogen 1-6 The alkyl group may be:
[0368] n8 is preferably an integer of 1 to 3.
[0369] In one embodiment, the solvent is R 84 R 85 R 86 Si-(O-SiR 87 R 88 ) m8 -R 89 It is.
[0370] In one embodiment, the solvent is (OSiR 87 R 88 ) m9 (OSiR 87 R 88 ) m9 is multiple OSiR 87 R 88 It is a cyclic siloxane formed by bonding units in a ring.
[0371] R 84 ~R 89 are each independently a hydrogen atom or C 1-6 Alkyl groups of the formula C 1-6 More preferably, the alkyl group 1-3 and more preferably a methyl group.
[0372] m8 is preferably an integer of 1 to 6, more preferably an integer of 1 to 5, and further preferably 1 to 2.
[0373] m9 is preferably an integer of 3 to 6, and more preferably an integer of 3 to 5.
[0374] In one embodiment, the solvent may be, for example, an aliphatic hydrocarbon such as hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, or mineral spirit; an aromatic hydrocarbon such as benzene, toluene, xylene, naphthalene, or solvent naphtha; an aromatic hydrocarbon such as 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, or ethyl 2-hydroxybutyrate. esters 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 ... Glycol ethers such as 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, 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;Polyfluoroaromatic hydrocarbons (e.g., 1,3-bis(trifluoromethyl)benzene); polyfluoroaliphatic hydrocarbons (e.g., C; 6 F 13 CH 2 CH 3 (For example, Asahiklin (registered trademark) AC-6000 manufactured by Asahi Glass Co., Ltd.), C 6 F 13 H (e.g., Asahiklin (registered trademark) AC-2000 manufactured by Asahi Glass Co., Ltd.), 1,1,2,2,3,3,4-heptafluorocyclopentane (e.g., Zeorora (registered trademark) H manufactured by Zeon Corporation); fluorine-containing hydrocarbons such as 1,1,2-trichloro-1,2,2-trifluoroethane, 1,2-dichloro-1,1,2,2-tetrafluoroethane, 1,1-dichloro-1,2,2,3,3-pentafluoropropane (HCFC225), and 1,3-bis(trifluoromethyl)benzene; CF 3 CH 2 OH, CF 3 CF 2 CH 2 OH, (CF 3 ) 2 Fluorine-containing alcohols such as CHOH; hydrofluoroethers (HFE) (e.g., perfluoropropyl methyl ether (C 3 F 7 OCH 3 ) (e.g., Novec (trademark) 7000 manufactured by Sumitomo 3M Co., Ltd.), perfluorobutyl methyl ether (C 4 F 9 OCH 3 ) (e.g., Novec (trademark) 7100 manufactured by Sumitomo 3M Co., Ltd.), perfluorobutyl ethyl ether (C 4 F 9 O.C. 2 H 5 ) (e.g., Novec (trademark) 7200 manufactured by Sumitomo 3M Limited), perfluorohexyl methyl ether (C 2 F 5 CF(OCH 3 ) C 3 F 7) (e.g., Novec™ 7300 from Sumitomo 3M Limited) (wherein the perfluoroalkyl and alkyl groups may be linear or branched), or CF 3 CH 2 OCF 2 CHF 2 (e.g., Asahiklin (registered trademark) AE-3000 manufactured by Asahi Glass Co., Ltd.), hydrofluoroolefins; CF 3 CH═CHCl (e.g., CELEFIN® 1233Z manufactured by Central Glass Co., Ltd.), CHF 2 Examples of the solvent include ethers such as CF═CHCl (for example, AMOLEA® AS-300 manufactured by Asahi Glass Co., Ltd.), cyclopentyl methyl ether, and the like; siloxanes such as hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, octamethylcyclotetrasiloxane, octamethylcyclopentasiloxane, decamethylcyclopentasiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, and tetradecamethylhexasiloxane, and dimethylsulfoxide. Alternatively, examples of the solvent include a mixture of two or more of these solvents. Among these, aliphatic hydrocarbons, esters, glycol ethers, alcohols, ether alcohols, and siloxanes are preferred. For example, hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, mineral spirits, methyl acetate, ethyl acetate, propyl acetate, n-butyl acetate, isopropyl acetate, isobutyl acetate, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, methanol, ethanol, isopropanol, n-butanol, isobutanol, tert-butanol, sec-butanol, diethylene glycol monomethyl ether, hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, tetradecamethylhexasiloxane, octamethylcyclotetrasiloxane, and octamethylcyclopentasiloxane are preferred.
[0375] 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:
[0376] Above R 3a are each independently a hydrogen atom or a hydrocarbon group. Such a hydrocarbon group may be substituted.
[0377] 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.
[0378] R 3a 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.
[0379] Above C 1-6 The alkyl group may be linear or branched, but is preferably linear. C 1-6 The alkyl group is preferably C 1-3 It is preferably an alkyl group, more preferably a methyl group.
[0380] The aryl group is preferably a phenyl group.
[0381] 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.
[0382] In another embodiment, R 3a is a phenyl group.
[0383] In another embodiment, R 3a is a methyl group or a phenyl group, preferably a methyl group.
[0384] Above R 1a are each independently a hydrogen atom or a hydrocarbon group, and 3a This has the same meaning as:
[0385] 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.
[0386] 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.
[0387] In another embodiment, R 1a is a phenyl group.
[0388] In another embodiment, R 1a is a methyl group or a phenyl group, preferably a methyl group.
[0389] 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.
[0390] a1 may be preferably 5-1000, more preferably 10-500, further preferably 15-200, and even more preferably 15-150.
[0391] Another silicone oil is (3b) below: R 1a -R SO2 -R 3a (3b) [In formula: R 1a are each independently a hydrocarbon group; R 3a are each independently a hydrocarbon group; R SO2 -R S -SiR 5 2 - and R S and R 5 has the same meaning as above.] Examples of the compound include compounds represented by the following formula:
[0392] 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.
[0393] 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.
[0394] 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 composition of the present disclosure.
[0395] In the composition 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 100 parts by mass of the total of the compounds of the present disclosure (when there are two or more types, the total of these, the same applies below).
[0396] The silicone oil contributes to improving the surface slipperiness of the surface treatment layer.
[0397] Examples of the alcohols include methanol, ethanol, iso-propanol, n-butanol, isobutanol, tert-butanol, sec-butanol, 3-pentanol, octyl alcohol, 3-methyl-3-methoxybutanol, and tert-amyl alcohol. Adding these alcohols to the composition improves the stability of the composition.
[0398] 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.
[0399] Examples of the aliphatic amine compound include diethylamine, triethylamine, etc. Examples of the aromatic amine compound include aniline, pyridine, etc.
[0400] 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.
[0401] The hydrolyzable group means a group that can undergo hydrolysis, similar to the hydrolyzable group in the above 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.
[0402] 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.
[0403] In one embodiment, the hydrolyzable group may be the same as the hydrolyzable group contained in the compound described above. By making the hydrolyzable groups in the compound and the transition metal compound the same, even if the hydrolyzable groups are exchanged with each other, the effect can be reduced.
[0404] In another embodiment, the hydrolyzable group may be different from the hydrolyzable group contained in the compound described above. By making the hydrolyzable groups in the compound and the transition metal compound different, the hydrolysis reactivity can be controlled.
[0405] In one embodiment, the hydrolyzable group and the hydrolyzable group contained in the compound may be interchangeable in the composition.
[0406] In a preferred embodiment, the transition metal compound is Ta(OR m ) 5 (In the formula, R m is a substituted or unsubstituted C 1-4 ), preferably Ta(OCH 2 CH 3 ) 5 , or Si(OR m ) 1-m1 R m’ m1 (In the formula, R m is a substituted or unsubstituted C 1-4 is an alkyl group, R m’ is C 1-4 is an alkyl group, and m1 is 0 or 1.) and preferably tetraethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, tetraisopropoxysilane, dimethyldiethoxysilane, or dimethyldimethoxysilane.
[0407] The catalyst may be contained in an amount of, for example, 0.0002% by mass or more based on the entire composition. The catalyst is preferably contained in an amount of, for example, 0.02% by mass or more based on the entire composition, and more preferably contained in an amount of, for example, 0.04% by mass or more based on the entire composition. The catalyst may be contained in an amount of, for example, 10% by mass or less based on the entire composition, and particularly 1% by mass or less. The composition 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.
[0408] 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 compound of the present disclosure.
[0409] The catalyst promotes the hydrolysis and dehydration condensation of the compounds of the present disclosure, and promotes the formation of the layer formed by the composition of the present disclosure.
[0410] Other examples of the other components include tetraethoxysilane, methyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, and methyltriacetoxysilane in addition to the above.
[0411] In addition to the components described above, the composition of the present disclosure may contain trace amounts of impurities such as Pt, Rh, Ru, 1,3-divinyltetramethyldisiloxane, triphenylphosphine, NaCl, KCl, and silane condensates.
[0412] In one embodiment, the compositions of the present disclosure are for dry coating processes, preferably vacuum deposition.
[0413] In one embodiment, the compositions of the present disclosure are for use in wet coating methods, preferably dip coating.
[0414] The compositions of the present disclosure can be impregnated into porous materials, such as porous ceramic materials, metal fibers, such as steel wool, and formed into pellets, which can be used, for example, in vacuum deposition.
[0415] The composition of the present disclosure is preferably used as a surface treatment agent or as a component of a surface treatment agent.
[0416] The articles of the present disclosure are described below.
[0417] 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.
[0418] 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.
[0419] For example, when the article to be manufactured is an optical component, the material constituting the surface of the substrate may be a material for optical components, such as glass or transparent plastic. When the article to be manufactured is an optical component, some layer (or film), such as a hard coat layer or an antireflection layer, may be formed on the surface (outermost layer) of the substrate. The antireflection layer may be either a single-layer antireflection layer or a multi-layer antireflection layer. Examples of inorganic substances that can be used for the antireflection layer include SiO 2 , SiO, ZrO 2 , TiO 2 , TiO, Ti 2 O 3 , Ti 2 O 5 , Al 2 O 3 , Ta 2 O 5 , Ta 3 O 5 ,Nb 2 O 5 , HfO 2 , Si 3 N 4 , CEO 2 , MgO, Y 2 O 3 , SnO 2 , MgF 2, WO 3 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 antireflection layer is formed, the outermost layer is preferably SiO 2 and / or SiO are preferably used. 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, and a liquid crystal display module, etc., depending on the specific specifications.
[0420] 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.
[0421] 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.
[0422] 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.
[0423] In a preferred embodiment, the substrate is glass, preferably sapphire glass, soda-lime glass, alkali aluminosilicate glass, borosilicate glass, alkali-free glass, crystal glass, quartz glass, or crystallized glass, and more preferably chemically strengthened soda-lime glass, chemically strengthened alkali aluminosilicate glass, or chemically bonded borosilicate glass.
[0424] In one embodiment, the article of the present disclosure may include an intermediate layer containing silicon oxide between the glass and the surface treatment layer. By providing such an intermediate layer, the adhesion between the glass and the surface treatment layer is improved, and durability is improved.
[0425] In a preferred embodiment, the intermediate layer may contain an alkali metal in addition to silicon oxide.
[0426] Examples of the alkali metal include lithium, sodium, potassium, etc. The alkali metal is preferably sodium.
[0427] The thickness of the intermediate layer is not particularly limited, but is preferably 1 to 200 nm, and particularly preferably 1 to 20 nm. By making the thickness of the intermediate layer equal to or greater than the lower limit of the above range, the effect of improving adhesiveness by the intermediate layer becomes greater.
[0428] The alkali metal atom concentration in the intermediate layer can be measured by various surface analysis devices, such as TOF-SIMS, XPS, and XRF.
[0429] The proportion of alkali metal atoms in the total atoms of the entire intermediate layer can be obtained by XPS depth profiling using ion sputtering, which is performed by alternating between XPS measurement and surface etching by ion sputtering using an ion gun built into the XPS instrument.
[0430] In the intermediate layer, the average value of the alkali metal concentration in a region 1 nm or less deep from the surface in contact with the surface treatment layer is obtained by obtaining a depth profile of the alkali metal atom concentration by TOF-SIMS (time-of-flight secondary ion mass spectrometry) depth profile analysis by ion sputtering, and then calculating the average value of the alkali metal atom concentration in the profile. The TOF-SIMS depth profile analysis by ion sputtering is performed by alternately repeating TOF-SIMS measurement and surface etching by ion sputtering using an ion gun built into the TOF-SIMS device.
[0431] 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.
[0432] 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.
[0433] 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.
[0434] 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.
[0435] Furthermore, coating by atmospheric pressure plasma method is also possible.
[0436] 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., C; 6 F 13 CH 2 CH 3 (For example, Asahiklin (registered trademark) AC-6000 manufactured by Asahi Glass Co., Ltd.), C 6 F 13 H (e.g., Asahiklin (registered trademark) AC-2000 manufactured by Asahi Glass Co., Ltd.), 1,1,2,2,3,3,4-heptafluorocyclopentane (e.g., Zeorora (registered trademark) H manufactured by Zeon Corporation); fluorine-containing hydrocarbons such as 1,1,2-trichloro-1,2,2-trifluoroethane, 1,2-dichloro-1,1,2,2-tetrafluoroethane, 1,1-dichloro-1,2,2,3,3-pentafluoropropane (HCFC225), and 1,3-bis(trifluoromethyl)benzene; CF 3 CH 2 OH, CF 3 CF 2 CH 2 OH, (CF 3 ) 2 Fluorine-containing alcohols such as CHOH; hydrofluoroethers (HFE) (e.g., perfluoropropyl methyl ether (C 3 F 7 OCH 3 ) (e.g., Novec (trademark) 7000 manufactured by Sumitomo 3M Co., Ltd.), perfluorobutyl methyl ether (C 4 F 9 OCH 3 ) (e.g., Novec (trademark) 7100 manufactured by Sumitomo 3M Co., Ltd.), perfluorobutyl ethyl ether (C 4 F 9 O.C. 2 H 5 ) (e.g., Novec (trademark) 7200 manufactured by Sumitomo 3M Limited), perfluorohexyl methyl ether (C 2 F 5 CF(OCH3 ) C 3 F 7 ) (e.g., Novec™ 7300 from Sumitomo 3M Limited) (wherein the perfluoroalkyl and alkyl groups may be linear or branched), or CF 3 CH 2 OCF 2 CHF 2 (e.g., Asahiklin (registered trademark) AE-3000 manufactured by Asahi Glass Co., Ltd.), hydrofluoroolefins; CF 3 CH═CHCl (e.g., CELEFIN® 1233Z manufactured by Central Glass Co., Ltd.), CHF 2Ethers such as CF═CHCl (e.g., AMOLEA® AS-300 manufactured by Asahi Glass Co., Ltd.), cyclopentyl methyl ether, etc.; siloxanes such as hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, octamethylcyclotetrasiloxane, octamethylcyclopentasiloxane, decamethylcyclopentasiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, and tetradecamethylhexasiloxane, etc.; dimethyl sulfoxide, etc. These solvents can be used alone or as a mixture of two or more kinds. Among them, aliphatic hydrocarbons, esters, glycol ethers, alcohols, ether alcohols, and siloxanes are preferred. For example, hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, mineral spirits, methyl acetate, ethyl acetate, propyl acetate, n-butyl acetate, isopropyl acetate, isobutyl acetate, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, methanol, ethanol, isopropanol, n-butanol, isobutanol, tert-butanol, sec-butanol, diethylene glycol monomethyl ether, hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, tetradecamethylhexasiloxane, octamethylcyclotetrasiloxane, and octamethylcyclopentasiloxane are particularly preferred.
[0437] In one embodiment, the solvent when using the wet coating method is, for example, R 90 Compounds represented by the formula R -OH can be used. 90 is a monovalent organic group, preferably C 1-20 Alkyl group or C 3-20 These groups are alkylene groups, and may be substituted with one or more substituents. Examples of the substituents include a hydroxyl group, -OR 91 (where R 91 is C 1-10 Alkyl groups, preferably C 1-3Alkyl groups, for example methyl groups, can be mentioned.
[0438] 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.
[0439] 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.
[0440] 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.
[0441] The surface treatment layer included in the article of the present disclosure can have high abrasion resistance.In addition to high abrasion resistance, the surface treatment layer can 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 can be suitably used as a functional thin film.
[0442] Therefore, the present disclosure further relates to an optical material having the above-mentioned surface treatment layer as the outermost layer.
[0443] 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.
[0444] 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.
[0445] 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.
[0446] The thickness of the layer is not particularly limited. In the case of an optical member, the thickness of the layer may be, for example, 1 to 50 nm, preferably 1 to 30 nm, and more preferably 1 to 15 nm, from the viewpoints of optical performance, abrasion resistance, and antifouling properties.
[0447] As an apparatus for performing X-ray photoelectron spectroscopy to measure the atomic composition and the ratio of constituent atoms of the surface treatment layer, an XPS, PHI5000VersaProbeII manufactured by ULVAC-PHI, Inc. can be used. The measurement conditions for XPS analysis are a monochromatic AlKα ray of 25 W for the X-ray source, a photoelectron detection area of 1400 μm × 300 μm, a photoelectron detection angle in the range of 20 degrees to 90 degrees (for example, 20 degrees, 45 degrees, 90 degrees), a pass energy of 23.5 eV, etc., and gas cluster ion beams, Ar ions, etc. can be used for sputtering. With the above apparatus and measurement conditions, the peak areas of C1s, O1s, and Si2p can be observed, and the atomic ratios of carbon, oxygen, and silicon can be calculated to determine the composition of the surface treatment layer and the intermediate layer.
[0448] It is also possible to carry out analysis in the depth direction. The measurement conditions for XPS analysis are: monochromatic AlKα radiation at 25 W as the X-ray source; photoelectron detection area of 1400 μm×300 μm; photoelectron detection angle in the range of 20 degrees to 90 degrees (for example, 20 degrees, 45 degrees, 90 degrees); pass energy of 23.5 eV; and Ar ions, gas cluster ions, C60 ions, etc. can be used as sputter ions. It is also possible to etch 1 to 100 nm by sputtering, and obtain the composition in the coating film at each etching depth.
[0449] By adjusting the photoelectron detection angle in the above XPS analysis, the detection depth can be appropriately adjusted. For example, a shallow angle close to 20 degrees can provide a detection depth of about 3 nm, while a deep angle close to 90 degrees can provide a detection depth of about 10 nm.
[0450] The intermediate layer containing silicon oxide can be formed by applying a silicon oxide precursor to the surface of the substrate. When the intermediate layer contains an alkali metal, the intermediate layer can be formed by applying a composition containing a silicon oxide precursor and an alkali metal source to the surface of the substrate.
[0451] Examples of the silicon oxide precursor include silicic acid, partial condensates of silicic acid, alkali metal silicates, silane compounds having a hydrolyzable group bonded to a silicon atom, and partial hydrolysis condensates of the silane compounds. Silicic acid and partial condensates thereof can be dehydrated and condensed to form silicon oxide, and alkali metal silicates can be converted to silicic acid and partial condensates thereof by using an acid or a cation exchange resin, and the resulting silicic acid and partial condensates can be dehydrated and condensed to form silicon oxide. Examples of the hydrolyzable group in the silane compound having a hydrolyzable group bonded to a silicon atom include an alkoxy group and a chlorine atom. The hydrolyzable group of the silane compound can be hydrolyzed to a hydroxyl group, and the resulting silanol compound can be dehydrated and condensed to form silicon oxide. Examples of the silane compound having a hydrolyzable group bonded to a silicon atom include alkoxysilanes such as tetraalkoxysilanes and alkyltrialkoxysilanes, and tetrachlorosilanes.
[0452] The alkali metal source includes alkali metal hydroxides, water-soluble alkali metal salts, etc. The water-soluble alkali metal salts include alkali metal carbonates, alkali metal hydrogencarbonates, alkali metal hydrochlorides, alkali metal nitrates, etc. The alkali metal source is preferably an alkali metal hydroxide or an alkali metal carbonate.
[0453] In addition, alkali metal silicate can be used as a silicon oxide precursor and an alkali metal source. The alkali metal silicate can be converted into silicon oxide via silicic acid, but a small amount of alkali metal may remain in the silicon oxide produced at that time. Therefore, the amount of the remaining alkali metal can be adjusted to obtain silicon oxide containing a predetermined amount of alkali metal atoms.
[0454] The thickness of the intermediate layer is not particularly limited, but is, for example, in the range of 1 to 50 nm, preferably 1 to 30 nm, more preferably 2 to 15 nm, and further preferably 3 to 10 nm.
[0455] 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
[0456] The present disclosure will be described below with reference to examples, but the present disclosure is not limited to the following examples.
[0457] (Synthesis Example 1) CH 3 CH 2 CH 2 CH 2 [Si(CH 3 ) 2 O] n Si(CH 3 ) 2 3.00 g of 1H (the average number of repeating units n is 12.0), 1.00 g of potassium tert-butoxide, 3.78 mL of allyl bromide, and 4.80 mL of tetrahydrofuran were added, and the mixture was heated to 40° C. and stirred for 7 hours. Then, the mixture was concentrated under reduced pressure to obtain compound (1)CH 3 CH 2 CH 2 CH 2 [Si(CH 3 ) 2 O] n Si(CH 3 ) 2 CH 2 CH 2 CH 2 OCH 2 CH 2 OCH 2 CH=CH 2 (The average value of the repeating unit number n is 12.0) 2.30 g was obtained.
[0458] 1 H NMR (CDCl 3, 400 MHz) δ[ppm]: -0.106-0.223 (m), 0.414-0.541 (m), 0.866-0.894 (m), 1.123-1.319 (m), 1.554-1.639 (m), 3.375-3.441 (m), 3.594-3.602 (m), 5.166-5.299(dd), 5.874-5.968 (m)
[0459] (Synthesis Example 2) 0.50 g of compound (1), 1.00 mL of toluene, and 25 μL of a xylene solution containing 2% Pt complex of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane were added, and the mixture was stirred at room temperature for 30 minutes. Then, 13.5 μL of aniline and 177.5 μL of trimethoxysilane were added, and the mixture was heated to 45° C. and stirred for 4 hours. Compound (2) CH 3 CH 2 CH 2 CH 2 [Si(CH 3 ) 2 O] n Si(CH 3 ) 2 CH 2 CH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 CH 2 Si(OCH 3 ) 3 (The average value of the repeating unit number n is 11.8) was obtained in an amount of 0.48 g.
[0460] 1 H NMR (CDCl 3 , 400 MHz) δ[ppm]: -0.098-0.231 (m), 0.523-0.563 (m), 0.652-0.693 (m), 0.872-0.907 (m), 1.290-1.327 (m), 1.581-1.734 (m), 3.388-3.466 (m), 3.569-3.581 (m)
[0461] (Surface treatment agent 1) The compound (2) obtained above was diluted to a 10 wt % solution in hexamethyldisiloxane, to obtain a surface treatment agent 1.
[0462] (Synthesis Example 3) In a glass flask, 14.2 g of 14-hydroxy-3,6,9,12-tetraoxatetradecyl p-toluenesulfonate, 6.90 g of 4-bromophenol, 305 mL of acetonitrile, and 5.52 g of potassium carbonate were added, and the flask was heated in an oil bath to an internal temperature of 80°C and stirred for 5 hours. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated to obtain a pale orange oil. This was purified by silica gel column chromatography (eluent: ethyl acetate, methanol) to obtain 13.9 g of compound (3) as a colorless oil.
[0463] 1H-NMR (400 MHz, Chloroform-D) δ 7.36 (d, J = 8.8 Hz, 2H), 6.80 (d, J = 8.8 Hz, 2H), 4.10 (t, J = 4.8 Hz, 2H), 3.73 (t, J = 4.8 Hz, 2H), 3.80-3.59 (m, 16H), 2.74 (brs, 1H)
[0464] Compound (3) TIFF2025062586000025.tif2455
[0465] (Synthesis Example 84) In a glass flask, 13.1 g of compound (3) and 250 mL of tetrahydrofuran were added, and the flask was placed in an ice bath to bring the internal temperature to 2°C. Then, 6.01 g of sodium hydride (60% paraffin oil dispersion) and 15.3 g of 11-bromo-1-undecene were added to the flask, and the flask was placed in an oil bath to bring the internal temperature to 70°C and stirred for 12 hours. The flask was cooled to room temperature, and water and ethyl acetate were added to the flask and stirred. The solution was transferred to a separatory funnel and the aqueous layer was removed. The remaining organic layer was washed twice with water, dried with magnesium sulfate, and concentrated under reduced pressure to obtain an orange oil. This was purified by silica gel column chromatography (eluent: heptane, ethyl acetate) to obtain 11.9 g of compound (4) as a slightly yellow oil.
[0466] 1H-NMR (400 MHz, Chloroform-D) δ 7.38 (d, J = 8.8 Hz, 2H), 6.82 (d, J = 8.8 Hz, 2H),4.15 (t, J = 4.8 Hz, 2H), 3.83 (t, J = 5.0 Hz, 2H), 3.75-3.72 (m, 2H), 3.69-3.63 (m, 12H), 3.59-3.56 (m, 2H), 3.40 (t, J = 6.6 Hz, 2H), 2.00 (m, 2H), 1.60-1.55 (m, 2H), 1.41-1.19 (m, 14H)
[0467] Compound (4) TIFF2025062586000026.tif2058
[0468] (Synthesis Example 5) In a glass flask, 1.0 g of compound (4) and 7 mL of tetrahydrofuran were added, and the flask was placed in a dry ice / acetone bath. 1.23 mL of a hexane solution containing 15% n-butyllithium was added dropwise, and the mixture was stirred with a magnetic stirrer for 1 hour. Then, 9 mL of a tetrahydrofuran solution containing 1.55 g of hexamethylcyclotrisiloxane was added dropwise to the flask, and the mixture was stirred at room temperature for 4 hours. Then, 0.59 g of 3-chloro-1,1,1,3,5,5,5-heptamethyltrisiloxane was added to the flask, and the mixture was stirred at room temperature for 18 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform) to obtain a slightly yellow oil. This oil was washed with acetonitrile and concentrated under reduced pressure to obtain 1.80 g of compound (5) as a slightly yellow oil. The average number of repeating units was 12.
[0469] 1H-NMR (400 MHz, Chloroform-D) δ 7.47 (d, J = 8.2 Hz, 2H), 6.91 (d, J = 8.7 Hz, 2H), 5.86-5.76 (m, 1H), 5.02-4.91 (m, 2H), 4.14 (t, J = 4.8 Hz, 2H), 3.86 (t, J = 5.0 Hz, 2H), 3.75-3.72 (m, 2H), 3.69-3.63 (m, 12H), 3.59-3.56 (m, 2H), 3.44 (t, J = 6.6 Hz, 2H), 2.04 (q, J = 7.0 Hz, 2H), 1.59-1.54 (m, 2H), 1.39-1.20 (m, 14H), 0.32 (s, 6H), 0.25--0.13 (m)
[0470] Compound (5) TIFF2025062586000027.tif2691
[0471] (Synthesis Example 6) A glass flask was charged with a stirrer tip, 1.80 g of compound (5), 91 μL of xylene solution containing 2% Pt complex of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, 13 μL of pyridine, 0.46 mL of trimethoxysilane, and 10 mL of toluene, and stirred at room temperature for 4 hours with a magnetic stirrer. After that, the mixture was concentrated under reduced pressure to obtain 1.83 g of compound (6) as a pale yellow oil. The average number of repeating units was 12.
[0472] 1H-NMR (400 MHz, Chloroform-D) δ 7.47 (d, J = 8.7 Hz, 2H), 6.91 (d, J = 8.7 Hz, 2H), 4.14 (t, J = 5.0 Hz, 2H), 3.86 (t, J = 5.0 Hz, 2H), 3.74-3.72 (m, 2H), 3.69-3.62 (m, 12H), 3.60-3.54 (m, 11H), 3.44 (t, J = 6.9 Hz, 2H), 1.59-1.55 (m, 2H), 1.41-1.39 (m, 2H), 1.33-1.26 (m, 14H), 0.66-0.62 (m, 2H), 0.31 (s, 6H), 0.25--0.07 (m)
[0473] Compound (6) TIFF2025062586000028.tif31130
[0474] (Surface treatment agent 2) The compound (6) obtained above was diluted to a 10 wt % solution in hexamethyldisiloxane, to obtain surface treatment agent 2.
[0475] (Comparative Example) (Surface treatment agent A) CH 3 CH 2 CH 2 CH 2 [Si(CH 3 ) 2 ] n Si(CH 3 ) 2 CH2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CONHCH 2 CH 2 CH 2 Si(OCH 3 ) 3 (The average number of repeating units n is 10) was diluted to a 10 wt % hexamethyldisiloxane solution, to obtain surface treatment agent A.
[0476] (Na-containing intermediate layer forming material) 2.2 g of sodium hydroxide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was dissolved in 24 g of distilled water to obtain an 8.4 mass% sodium hydroxide aqueous solution. 24 g of this 8.4 mass% sodium hydroxide aqueous solution was mixed with 20 g of MS gel (MSGEL D-100-60A (manufactured by AGC Si-Tech Co., Ltd.) to absorb the sodium hydroxide aqueous solution into the MS gel. The MS gel that absorbed the sodium hydroxide aqueous solution was dried at 25°C for 8 hours, then molded with a tablet molding machine (4 MPa for 1 minute) and baked at 1,000°C for 1 hour to obtain a molded body 1 (pellet).
[0477] (Formation of surface treatment layer) (Example 1 and Comparative Example 1) The surface treatment agent 1 and the surface treatment agent A prepared above were vacuum-deposited on a 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 -3The chamber was evacuated to a pressure of 100 Pa or less. After that, a silicon dioxide film containing Na was formed to a thickness of 7 nm by electron beam deposition using the molded body 1, and the boat was then heated by resistance heating to form a surface treatment layer. After that, a heat treatment was performed in an oven at 150° C. for 2 hours to obtain a surface treatment layer.
[0478] <Evaluation> [Weather resistance evaluation] (Initial evaluation) As an initial evaluation (before UV irradiation), after the formation of the surface treatment layer, the excess on the surface was wiped off, and then the static contact angle of water was measured. The contact angle was measured using a fully automatic contact angle meter DropMaster700 (manufactured by Kyowa Interface Science Co., Ltd.) in an environment of 25°C. Specifically, the substrate having the surface treatment layer to be measured was placed horizontally, water was dripped onto the surface from a microsyringe, and a still image was taken 1 second after the dripping with a video microscope to measure the static contact angle. The static contact angle was measured at five different points on the surface treatment layer of the substrate, and the average value was calculated.
[0479] (Evaluation after weather resistance test) A weather resistance test was conducted on the surface treatment layer formed. The accelerated weather resistance test is a test in which UV irradiation is performed as follows. UV irradiation was performed using a 7.5 kW xenon lamp (manufactured by Suga Test Instruments, irradiance 62 W / m2 at 300 to 400 nm), with the distance between the lamp and the surface treatment layer of the substrate set to 290 mm, the temperature of the plate on which the substrate was placed set to 55°C, and the humidity set to 55%. After 300 hours of UV irradiation, the surface treatment layer was wiped with Kimwipe (trade name, manufactured by Jujo Kimberly Co., Ltd.) sufficiently soaked in ethanol, and then dried. Immediately thereafter, the static contact angle of water was measured. The evaluation results are shown in Table 1 below.
[0480] [Table 1]
[0481] The surface treatment agent of the present disclosure can be suitably used for a wide variety of applications.
Claims
1. The following formula (1): 【Chemistry 1】 [In the formula: R S is a monovalent group containing one or more Si atoms to which a hydroxyl group or a hydrolyzable group is not directly bonded, X 1 is a divalent to decavalent group containing two or more ether bonds, R Si is a monovalent group containing a Si atom having a hydroxyl group or a hydrolyzable group bonded thereto, α is an integer from 1 to 9. A compound represented by the formula:
2. R S is R 1 -R S1 -(SiR 2 2 ) s - and R 1 is a hydrocarbon group, or R 1a na R 1b 3-na Si-(O) z -: R 1a are each independently R 1d -(SiR 1d 2 -R 1c ) ma - is a group represented by R 1c each independently represents an oxygen atom or C 1-6 is an alkylene group, R 1d are each independently a hydrocarbon group or R 1a’ and R 1a’ is R 1a is equivalent to Each m is independently an integer from 1 to 5, However, R 1a Medium, R 1a’ is 20 or less, R 1b are each independently a hydrocarbon group; n a is an integer from 1 to 3, z is 0 or 1; R S1 are each independently a single bond or a group represented by the following formula: 【Chemistry 2】 (In the formula: R 3 are each independently 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 are each independently 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 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; x+y+z is 1 or greater; 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 2 are each independently a hydrocarbon group; s is 0 or 1; The compound of claim 1.
3. R 1 is R 1a na R 1b 3-na Si—O—, R 1a are each independently -(R 1c -SiR 1d 2 ) ma -R 1d is a group represented by R 1c each independently represents an oxygen atom or C 1-6 is an alkylene group, R 1d are each independently a hydrocarbon group or R 1a’ and R 1a’ is R 1a is equivalent to Each m is independently an integer from 1 to 5, However, R 1a Medium, R 1a’ is 20 or less, R 1b are each independently a hydrocarbon group; n a is an integer from 1 to 3, The compound according to claim 2, wherein the compound is a group represented by the formula:
4. R 1a are each independently -(OSiR 1d 2 ) ma -R 1d is a group represented by R 1d are each independently a hydrocarbon group or R 1a’ and Each m is independently 1 or 2; R 1b are each independently a hydrocarbon group; n a is an integer from 1 to 3; The compound according to claim 2.
5. R 1d is C 1-4 The compound of claim 2 which is an alkyl group.
6. X 1 is -(O) z1 - [(CH 2 ) nb O] nc The compound according to claim 1, comprising a group represented by the formula: - (wherein nb is an integer of 1 to 10, nc is an integer of 1 to 30, and z1 is 0 or 1).
7. X 1 is -(O) z1 - [CH 2 CH 2 O] nc The compound according to claim 1, comprising a group represented by the formula: - (wherein nc is an integer of 1 to 8, and z1 is 0 or 1).
8. X 1 can further include alkylene, phenylene, -CO-, -COO-, -NR x1 --CONR x1 --, --OCONR x1 --, --NR x1 -CO-NR x1 -, -O-, -S-, -O-(CH 2 ) x1 -CONR x1 -, or -O-(CH 2 ) x1 is a divalent organic group containing —CO—, R x1 is a hydrogen atom or C 1-6 is an alkyl group, x1 is an integer from 1 to 20; The compound of claim 1.
9. X 1 is represented by the following formula: -X 11 -X 12 -X 13 - [In the formula: X 11 is a single bond or a divalent group, X 12 is -(O) z1 - [(CH 2 ) nb O] nc - (wherein nb is an integer of 1 to 10, nc is an integer of 1 to 8, and z1 is 0 or 1), X 13 is a single bond or a divalent group. The compound according to claim 1 , wherein the compound is a group represented by the formula:
10. R Si is represented by the following formula (S1), (S2), (S3), (S4), or (S5): 【Chemistry 3】 [In the formula: R 11 are each independently a hydroxyl group or a hydrolyzable group, R 12 are each independently a monovalent organic group, n1 is (SiR 11 n1 R 12 3-n1 ) each independently represents an integer from 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 more; 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 Each independently represents -Z 1 -SiR 21 p1 R 22 q1 R 23 r1 and Z 1 are each independently a divalent organic group, R 21 Each independently represents -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, Each p1 is independently an integer from 0 to 3; Each q1 is independently an integer from 0 to 3, Each r1 is independently an integer from 0 to 3; the sum of p1, q1 and r1 is 3; Z 1’ are each independently a divalent organic group, R 21’ Each independently represents -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, Each 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; the sum of p1', q1' and r1' is 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 from 0 to 3, Each r1″ is independently an integer from 0 to 3; the sum of q1″ and r1″ is 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 from 0 to 3; Each l1 is independently an integer from 0 to 3; Each m1 is independently an integer of 0 to 3; the sum of k1, l1 and m1 is 3; In the formula (S3), there are at least two Si atoms having hydroxyl groups or hydrolyzable groups bonded thereto, R d1 Each independently represents -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 Each independently represents -Z 2’ -CR 32’ q2’ R 33’ r2’ and R 32 Each independently represents -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 from 0 to 3, Each r2 is independently an integer from 0 to 3; the sum of p2, q2 and r2 is 3; Z 2’ each independently represents a single bond, an oxygen atom, or a divalent organic group, R 32’ Each independently represents -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, the sum of q2′ and r2′ is 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 from 0 to 3; R e1 Each independently represents -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 from 0 to 3; Each l2 is independently an integer from 0 to 3; Each m2 independently represents an integer of 0 to 3. the sum of k2, l2 and m2 is 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 Each independently represents -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 compound according to claim 1 , wherein the compound is a group represented by the formula:
11. R S is represented by the following formula: R 1 -[Si(EH 3 ) 2 -O] x -Si (CH) 3 ) 2 - [In the formula, R 1 is an alkyl group having 1 to 6 carbon atoms or R 1a na R 1b 3-na Si-(O) z - and R 1a (CH 3 ) 3 SiO-, R 1b is an alkyl group having 1 to 4 carbon atoms, na is 2 or 3; x is an integer from 5 to 50. is a group represented by X 1 is represented by the following formula: -X 11 -X 12 -X 13 - [In the formula: X 11 is C 1-6 an alkylene group or a phenylene group, X 12 is -O-[(CH 2 ) nb O] nc - (In the formula, nb is an integer of 2 to 4, nc is an integer of 1 to 5, and z1 is 0 or 1.) is a group represented by X 13 is C 1-12 is an alkylene group. is a group represented by R Si is represented by the following formula: -SiR 11 3 [In the formula, R 11 is -OR h and R h is an alkyl group having 1 to 4 carbon atoms. is a group represented by α is 1, The compound of claim 1.
12. 2. The compound of claim 1, wherein the compound is: CH 3 CH 2 CH 2 CH 2 [Si(CH 3 ) 2 O] n H 3 ) 2 CH 2 CH 2 CH 2 SO 2 CH 2 SO 2 CH 2 CH 2 H. 3 ) 3 (Wherein, TMSO is (CH 3 ) 3 SiO-, and n is 3 to 100.
13. 2. The compound of claim 1, wherein the compound is: CH 3 CH 2 CH 2 CH 2 [Si(CH 3 ) 2 O] n H 3 ) 2 CH 2 CH 2 CH 2 SO 2 CH 2 SO 2 CH 2 CH 2 H. 3 ) 3 (Wherein, TMSO is (CH 3 ) 3 SiO-, and n is 10 to 30.
14. A surface treatment agent comprising the compound according to any one of claims 1 to 13.
15. The surface treatment agent according to claim 14, further comprising a condensate of the compound according to claim 1.
16. The surface treatment agent according to claim 14, which is for vacuum deposition.
17. The surface treatment agent according to claim 14, which is for wet coating.
18. A pellet comprising the surface treatment agent according to claim 14.
19. An article comprising a substrate and a layer formed on the substrate from a compound according to any one of claims 1 to 13.
20. 20. The article of claim 19, comprising an intermediate layer between the substrate and the layer comprising silicon oxide.
21. 21. The article of claim 20, wherein the intermediate layer comprises alkali metal atoms.
22. 22. The article of claim 21, wherein at least a portion of the alkali metal atoms are sodium atoms.
23. 20. The article of claim 19 which is an optical component.
24. 20. The article of claim 19 which is a display.
25. formula: R S -X 1a -CH=CH 2 [In the formula: R S is a monovalent group containing one or more Si atoms to which a hydroxyl group or a hydrolyzable group is not directly bonded, X 1a is a divalent group containing two or more ether bonds. A compound represented by the formula:
26. formula: R S -X 1a -CONR 51 -(CH 2 ) x -CH=CH 2 [In the formula: R S is a monovalent group containing one or more Si atoms to which a hydroxyl group or a hydrolyzable group is not directly bonded, X 1a is a divalent group containing two or more ether bonds, R 51 is a hydrogen atom or a monovalent hydrocarbon group, x is an integer from 0 to 30. The compound according to claim 25 ,
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