Fluorine-containing silane compound

Abstract

To provide a new fluorine-containing silane compound.SOLUTION: Wherein Rf1 is each independently a group having CF3 at the terminal, provided that the terminal CF3 does not have CF2 at the adjacent position, XA is each independently a single bond, an oxygen atom, or a divalent to decavalent organic group, RSi is a monovalent group containing a Si atom to which a hydroxyl group or a hydrolyzable group is bonded, α1 is an integer of 1 to 9, and α2 is an integer of 1 to 9. The fluorine-containing silane compound is represented by formula (1).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present disclosure relates to a fluorine-containing silane compound. [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] Japanese Patent Application Publication No. 2019-44179 Summary of the Invention [Problem to be solved by the invention]

[0004] An object of the present disclosure is to provide a new fluorine-containing silane compound. [Means for solving the problem]

[0005] The present disclosure includes the following aspects. [1] The following formula (1): [ka] [In formula: Rf 1 are each independently a group having CF3 at its terminal, provided that the terminal CF3 does not have a CF2 at the adjacent position, X A are each independently a single bond, an oxygen atom, or a divalent to decavalent organic group, R Si is a monovalent group containing a Si atom to which a hydroxyl group or a hydrolyzable group is bonded, α1 is an integer from 1 to 9; and α2 is an integer from 1 to 9. A fluorine-containing silane compound represented by the formula: [2] Rf 1 are each independently R A1 -X B - [In formula: R A1 are CF3-, CF3O-, CF3NH-, CF3CH2NH-, (CF3)2N-, (CF3CH2)2N-, CF3S-, CF3C(=O)-, CF3CH2C(=O)-, CF3C(=O)O-, CF3CH2OC(=O)-, CF3CONH-, CF3CH2 CONH-, CF3NHCO-, CF3CH2NHCO-, CF3CON(CF3)-, CF3CH2CON(CF3)-, CF3CON(CH2CF3)-, CF3CH2CON(CH2CF3)-, (CF3)2NCO- or (CF3CH2)2NCO-, X B teeth, single bond, a group containing a divalent siloxane group, or -(CFH) a1 -(CH2) b1 -(O) c1 -(C(R A2 ) e1 H 2-e1 ) d1 -(NR A3 ) f1 - (In the formula: R A2 is a monovalent group having CF3-, CF3O-, CF3NH-, CF3CH2NH-, (CF3)2N-, (CF3CH2)2N-, CF3S-, CF3C(=O)-, CF3CH2C(=O)-, CF3C(=O)O-, CF3CH2OC(=O)-, CF3CONH-, CF3CH2CONH-, CF3NHCO-, CF3CH2NHCO-, CF3CON(CF3)-, CF3CH2CON(CF3)-, CF3CON(CH2CF3)-, CF3CH2CON(CH2CF3)-, (CF3)2NCO- or (CF3CH2)2NCO-, R A3is a monovalent group having a hydrogen atom or CF3-, CF3O-, CF3NH-, CF3CH2NH-, (CF3)2N-, (CF3CH2)2N-, CF3S-, CF3C(=O)-, CF3CH2C(=O)-, CF3C(=O)O-, CF3CH2OC(=O)-, CF3CONH-, CF3CH2CONH-, CF3NHCO-, CF3CH2NHCO-, CF3CON(CF3)-, CF3CH2CON(CF3)-, CF3CON(CH2CF3)-, CF3CH2CON(CH2CF3)-, (CF3)2NCO-, or (CF3CH2)2NCO-; a1 is an integer from 0 to 200, b1 is an integer from 0 to 200, c1 is an integer from 0 to 200, d1 is an integer from 0 to 200, e1 is 1 or 2, f1 is an integer from 0 to 200, The repeating units enclosed in parentheses and designated by the symbols a1, b1, c1, d1, and f1 may occur in any order. is a group represented by the following formula: The fluorine-containing silane compound according to the above item [1], wherein the fluorine-containing silane compound is a group represented by the formula: [3] R A1 The fluorine-containing silane compound according to the above [2], wherein is CF3O-, CF3NH-, or (CF3)2N-. [4] R A2 The fluorine-containing silane compound according to the above [2] or [3], wherein is a monovalent group having CF3O-, CF3NH-, or (CF3)2N-. [5] R A3 The fluorine-containing silane compound according to any one of the above [2] to [4], wherein is a hydrogen atom or a monovalent group having CF3O-. [6] X B is -(CFH) a1 -(CH2) b1 -(O) c1 - [In formula: a1 is an integer from 0 to 200, b1 is an integer from 0 to 200, c1 is an integer from 0 to 10, The repeating units enclosed in parentheses and designated by the symbols a1, b1, and c1 may occur in any order.] The fluorine-containing silane compound according to the above [2] or [3], wherein the fluorine-containing silane compound is a group represented by the formula: [7] X B is -(CH2) b1 - [In the formula, b1 is an integer of 0 to 36.] The fluorine-containing silane compound according to the above [2] or [3], wherein the fluorine-containing silane compound is a group represented by the formula: [8] X B is -(CH2) g1 -R S -(CH2) g1 - [In formula: Each g1 is independently an integer of 0 to 30, R S is expressed by the following formula: [ka] (In the formula: R 3 are each independently a single bond, C 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 1-12Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 -, or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 6 are each independently 1-6 is an alkylene group, R 7 each independently represents an optionally substituted phenylene group or naphthylene group, R 8 are each independently 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 repeating units enclosed in parentheses with x, y, or z may occur in any order in the formula. is a group represented by the following formula: The fluorine-containing silane compound according to the above [2] or [3], wherein the fluorine-containing silane compound is a group represented by the formula: [9] X A is a single bond, -(X 52 ) l5- or the formula (X A1 ): [ka] [In formula: X 52 each independently represents -O-, -S-, o-, m- or p-phenylene group, -CO-, -C(O)O-, -OC(O)-, or -CONR 54 -, -NR 54 CO-, -O-CONR 54 -, -NR 54 CO-O-, -NR 54 CONR 54 -, -NR 54 - and -(CH2) n5 - is a group selected from the group consisting of R 54 are each independently a hydrogen atom or a monovalent organic group, n5 each independently represents an integer of 1 to 30, l5 is an integer from 1 to 10, X a are each independently a single bond or a divalent linking group. The fluorine-containing silane compound according to any one of the above [1] to [8], wherein the fluorine-containing silane compound is a group represented by the following formula:

[10] R Si is 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 ) units are each independently an integer of 0 to 3, X 11 are each independently a single bond or a divalent organic group, R13 are each independently a hydrogen atom or a monovalent organic group, each t is independently an integer of 2 or greater; R 14 are each independently a hydrogen atom, a halogen atom or -X 11 -SiR 11 n1 R 12 3-n1 and 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, 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 each independently represents an integer of 0 to 3, Each q1 is independently an integer of 0 to 3, Each r1 is independently an integer of 0 to 3, Z 1’ are each independently a divalent organic group, R 21’ are each independently -Z 1” -SiR 22” q1” R 23” r1” and; R22’ are each independently a hydroxyl group or a hydrolyzable group, R 23’ are each independently a monovalent organic group, p1' is independently an integer of 0 to 3, Each q1' is independently an integer of 0 to 3, each r1' is independently an integer of 0 to 3; Z 1” are each independently a divalent organic group, R 22” are each independently a hydroxyl group or a hydrolyzable group, R 23” are each independently a monovalent organic group, q1″ are each independently an integer of 0 to 3, r1″ are each independently an integer of 0 to 3, R b1 are each independently a hydroxyl group or a hydrolyzable group, R c1 are each independently a monovalent organic group, k1 each independently represents an integer of 0 to 3, l1 are each independently an integer of 0 to 3, m1 each independently represents an integer of 0 to 3, R d1 are each independently -Z 2 -CR 31 p2 R 32 q2 R 33 r2 and Z 2 are each independently a single bond, an oxygen atom, or a divalent organic group, R 31 are each independently -Z 2’ -CR 32’ q2’ R 33’ r2’ and R 32 are each independently -Z 3 -SiR34 n2 R 35 3-n2 and R 33 are each independently a hydrogen atom, a hydroxyl group, or a monovalent organic group, p2 each independently represents an integer of 0 to 3, Each q2 is independently an integer of 0 to 3, Each r2 is independently an integer of 0 to 3, Z 2’ are each independently a single bond, an oxygen atom, or a divalent organic group, R 32’ are each independently -Z 3 -SiR 34 n2 R 35 3-n2 and R 33’ are each independently a hydrogen atom, a hydroxyl group, or a monovalent organic group, each q2' independently represents an integer of 0 to 3; r2' are each independently an integer of 0 to 3, Z 3 are each independently a single bond, an oxygen atom, or a divalent organic group; R 34 are each independently a hydroxyl group or a hydrolyzable group, R 35 are each independently a monovalent organic group, n2 each independently represents an integer of 0 to 3, R e1 are each independently -Z 3 -SiR 34 n2 R 35 3-n2 and R f1 are each independently a hydrogen atom, a hydroxyl group, or a monovalent organic group, k2 each independently represents an integer of 0 to 3, l2 are each independently an integer of 0 to 3, Each m2 is independently an integer of 0 to 3. 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 are each independently a single bond, an oxygen atom, or a divalent organic group, k3 is 1 or 2, l3 is 0 or 1, However, in formula (S1), (S2), (S3), (S4), or (S5), there are at least two Si atoms to which hydroxyl groups or hydrolyzable groups are bonded.] The fluorine-containing silane compound according to any one of the above [1] to [9], wherein the fluorine-containing silane compound is a group represented by the following formula:

[11] Rf 1 is R A1 -X B - and R A1 is CF3- or CF3O-, X B is a single bond, X A is -(p-phenylene) v1 -(CH2) v2 -R 57 v3 -(CH2) v4 - and R 57 is -CONH-, -NHCO-, -COO-, or -O-, v1 is 0 or 1, v2 is an integer between 0 and 20, v3 is 0 or 1, v4 is an integer from 2 to 20, R Si -SiR 11 3, R 11 is a methoxy group, α1 is 1, α2 is 1, The fluorine-containing silane compound according to any one of the above items [1] to

[10] .

[12] The following compound: The fluorine-containing silane compound according to any one of the above [1] to

[11] , selected from TIFF2026035630000005.tif65144.

[13] A surface treatment agent comprising the fluorine-containing silane compound according to any one of the above [1] to

[12] .

[14] The surface treatment agent according to the above

[13] , further comprising a condensate of the fluorine-containing silane compound according to any one of the above [1] to

[12] .

[15] Furthermore, R 90 -OH (where R 90 is a monovalent organic group.

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

[13] to

[15] , which is for vacuum deposition.

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

[13] to

[15] , which is for wet coating.

[18] Pellets containing the surface treatment agent according to any one of the above items

[13] to

[17] .

[19] An article comprising a substrate and a layer formed on the substrate from the fluorine-containing silane compound according to any one of the above [1] to

[12] .

[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

[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.

[23] The article according to any one of the above items

[19] to

[22] , which is an optical member.

[24] The article according to

[23] above, which is a display. [Effects of the Invention]

[0006] According to the present disclosure, a new fluorine-containing silane compound can be provided. DETAILED DESCRIPTION OF THE INVENTION

[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. A hydrocarbon group derivative refers to a group having one or more N, O, S, Si, amide, sulfonyl, siloxane, carbonyl, carbonyloxy, etc. at the end of the hydrocarbon group or in the molecular chain. As used herein, the term "divalent organic group" is not particularly limited, but includes a divalent group in which one hydrogen atom has been further eliminated from a hydrocarbon group.

[0008] As used herein, the term "hydrocarbon group" refers to a group containing carbon and hydrogen, with one hydrogen atom removed from the molecule. Examples of such hydrocarbon groups include, but are not limited to, hydrocarbon groups having 1 to 20 carbon atoms, such as aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The "aliphatic hydrocarbon group" may be linear, branched, or cyclic, and may be saturated or unsaturated. The hydrocarbon group may also contain one or more ring structures. The hydrocarbon group may be substituted with one or more substituents. The hydrocarbon group may have one or more N, O, S, Si, amide, sulfonyl, siloxane, carbonyl, carbonyloxy, etc., at its terminal or within the molecular chain.

[0009] As used herein, the substituent of the "hydrocarbon group" is not particularly limited, but examples thereof include a halogen atom; a C 1-6 Alkyl group, C 2-6 Alkenyl group, C 2-6 Alkynyl group, C 3-10 Cycloalkyl groups, C 3-10 Unsaturated cycloalkyl groups, 5-10 membered heterocyclyl groups, 5-10 membered unsaturated heterocyclyl groups, C 6-10 Examples 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 a hydrolysis reaction, i.e., a group that can be removed from the main skeleton of a compound by a hydrolysis reaction. 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 R include unsubstituted alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, and isobutyl; and substituted alkyl groups such as chloromethyl. Among them, alkyl groups, particularly unsubstituted alkyl groups, are preferred, with methyl or ethyl groups being more preferred. In one embodiment, R h is a methyl group, and in another embodiment, R h is an ethyl group.

[0011] [Fluorine-containing silane compounds] The fluorine-containing silane compound of the present disclosure is represented by the following formula (1): [ka] [In formula: Rf1 are each independently a group having CF3 at its terminal, provided that the terminal CF3 does not have a CF2 at the adjacent position, X A are each independently a single bond, an oxygen atom, or a divalent to decavalent organic group, R Si is a monovalent group containing a Si atom to which a hydroxyl group or a hydrolyzable group is bonded, α1 is an integer from 1 to 9; and α2 is an integer from 1 to 9. It is a fluorine-containing silane compound represented by the formula:

[0012] Rf 1 are each independently a group having CF3 at its terminal.

[0013] Rf 1 are each independently preferably R A1 -X B - [In formula: R A1 are CF3-, CF3O-, CF3NH-, CF3CH2NH-, (CF3)2N-, (CF3CH2)2N-, CF3S-, CF3C(=O)-, CF3CH2C(=O)-, CF3C(=O)O-, CF3CH2OC(=O)-, CF3CONH-, CF3CH2 CONH-, CF3NHCO-, CF3CH2NHCO-, CF3CON(CF3)-, CF3CH2CON(CF3)-, CF3CON(CH2CF3)-, CF3CH2CON(CH2CF3)-, (CF3)2NCO- or (CF3CH2)2NCO-, X B teeth, single bond, a group containing a divalent siloxane group, or -(CFH) a1 -(CH2) b1 -(O) c1 -(C(R A2 ) e1 H 2-e1 ) d1 -(NR A3 ) f1- (In the formula: R A2 is a monovalent group having CF3-, CF3O-, CF3NH-, CF3CH2NH-, (CF3)2N-, (CF3CH2)2N-, CF3S-, CF3C(=O)-, CF3CH2C(=O)-, CF3C(=O)O-, CF3CH2OC(=O)-, CF3CONH-, CF3CH2CONH-, CF3NHCO-, CF3CH2NHCO-, CF3CON(CF3)-, CF3CH2CON(CF3)-, CF3CON(CH2CF3)-, CF3CH2CON(CH2CF3)-, (CF3)2NCO- or (CF3CH2)2NCO-, R A3 is a monovalent group having a hydrogen atom or CF3-, CF3O-, CF3NH-, CF3CH2NH-, (CF3)2N-, (CF3CH2)2N-, CF3S-, CF3C(=O)-, CF3CH2C(=O)-, CF3C(=O)O-, CF3CH2OC(=O)-, CF3CONH-, CF3CH2CONH-, CF3NHCO-, CF3CH2NHCO-, CF3CON(CF3)-, CF3CH2CON(CF3)-, CF3CON(CH2CF3)-, CF3CH2CON(CH2CF3)-, (CF3)2NCO-, or (CF3CH2)2NCO-; a1 is an integer from 0 to 200, b1 is an integer from 0 to 200, c1 is an integer from 0 to 200, d1 is an integer from 0 to 200, e1 is 1 or 2, f1 is an integer from 0 to 200, The repeating units enclosed in parentheses and designated by the symbols a1, b1, c1, d1, and f1 may occur in any order. is a group represented by the following formula: It can be a group represented by the following formula:

[0014] R A1are CF3-, CF3O-, CF3NH-, CF3CH2NH-, (CF3)2N-, (CF3CH2)2N-, CF3S-, CF3C(=O)-, CF3CH2C(=O)-, CF3C(=O)O-, CF3CH2OC(=O)-, CF3CONH-, CF3CH2 CONH-, CF3NHCO-, CF3CH2NHCO-, CF3CON(CF3)-, CF3CH2CON(CF3)-, CF3CON(CH2CF3)-, CF3CH2CON(CH2CF3)-, (CF3)2NCO- or (CF3CH2)2NCO-. R A1 may preferably be CF3O-, CF3NH-, (CF3)2N-, CF3S-, CF3C(=O)-, CF3C(=O)O-, CF3OC(=O)-, CF3CONH-, CF3NHCO-, CF3CON(CF3)-, or (CF3)2NCO-, more preferably CF3O-, CF3NH-, or (CF3)2N-.

[0015] In one embodiment, R A1 can be CF3O-.

[0016] In another embodiment, R A1 can be CF3NH- or (CF3)2N-, preferably CF3NH-.

[0017] X B teeth, single bond, a group containing a divalent siloxane group, or -(CFH) a1 -(CH2) b1 -(O) c1 -(C(R A2 ) e1 H 2-e1 ) d1 -(NR A3 ) f1 - (In the formula: R A2 is a monovalent group having CF3-, CF3O-, CF3NH-, (CF3)2N-, CF3S-, CF3C(=O)-, CF3C(=O)O-, CF3OC(=O)-, CF3CONH-, or CF3CON(CF3)-; R A3 is a monovalent group having a hydrogen atom or CF3-, CF3O-, CF3NH-, (CF3)2N-, CF3S-, CF3C(=O)-, CF3C(=O)O-, CF3OC(=O)-, CF3CONH-, or CF3CON(CF3)-, a1 is an integer from 0 to 200, b1 is an integer from 0 to 200, c1 is an integer from 0 to 200, d1 is an integer from 0 to 200, e1 is 1 or 2, f1 is an integer from 0 to 200, The repeating units enclosed in parentheses and designated by the symbols a1, b1, c1, d1, and f1 may occur in any order. It is a group represented by the formula:

[0018] In one embodiment, X B is a single bond.

[0019] In another embodiment, X B teeth, -(CFH) a1 -(CH2) b1 -(O) c1 -(C(R A2 ) e1 H 2-e1 ) d1 -(NR A3 ) f1 - (In the formula: R A2 is a monovalent group having CF3-, CF3O-, CF3NH-, CF3CH2NH-, (CF3)2N-, (CF3CH2)2N-, CF3S-, CF3C(=O)-, CF3CH2C(=O)-, CF3C(=O)O-, CF3CH2OC(=O)-, CF3CONH-, CF3CH2CONH-, CF3NHCO-, CF3CH2NHCO-, CF3CON(CF3)-, CF3CH2CON(CF3)-, CF3CON(CH2CF3)-, CF3CH2CON(CH2CF3)-, (CF3)2NCO- or (CF3CH2)2NCO-, a1 is an integer from 0 to 200, b1 is an integer from 0 to 200, c1 is an integer from 0 to 200, d1 is an integer from 0 to 200, e1 is 1 or 2, f1 is an integer from 0 to 200, The repeating units enclosed in parentheses and designated by the symbols a1, b1, c1, d1, and f1 may occur in any order. It is a group represented by the formula:

[0020] R A2 is a monovalent group having CF3-, CF3O-, CF3NH-, CF3CH2NH-, (CF3)2N-, (CF3CH2)2N-, CF3S-, CF3C(=O)-, CF3CH2C(=O)-, CF3C(=O)O-, CF3CH2OC(=O)-, CF3CONH-, CF3CH2CONH-, CF3NHCO-, CF3CH2NHCO-, CF3CON(CF3)-, CF3CH2CON(CF3)-, CF3CON(CH2CF3)-, CF3CH2CON(CH2CF3)-, (CF3)2NCO-, or (CF3CH2)2NCO-.

[0021] R A2 is preferably a monovalent group having CF3O-, CF3NH-, (CF3)2N-, CF3S-, CF3C(=O)-, CF3C(=O)O-, CF3OC(=O)-, CF3CONH-, or CF3CON(CF3)-, more preferably a monovalent group having CF3O-, CF3NH-, or (CF3)2N-.

[0022] R A2 is preferably R A2’ -X A2 - [In formula: R A2’are CF3-, CF3O-, CF3NH-, CF3CH2NH-, (CF3)2N-, (CF3CH2)2N-, CF3S-, CF3C(=O)-, CF3CH2C(=O)-, CF3C(=O)O-, CF3CH2OC(=O)-, CF3CONH-, CF3CH2CONH-, CF3NHCO-, CF3CH2NHCO-, CF3CON(CF3)-, CF3CH2CON(CF3)-, CF3CON (CH2CF3)-, CF3CH2CON(CH2CF3)-, (CF3)2NCO- or (CF3CH2)2NCO-, preferably CF3O-, CF3NH-, (CF3)2N-, CF3S-, CF3C(=O)-, CF3C(=O)O-, CF3OC(=O)-, CF3CONH- or CF3CON(CF3)-, more preferably CF3O-, CF3NH- or (CF3)2N-; X A2 is a single bond or a divalent group. It can be a group represented by the following formula:

[0023] X A2 is preferably a single bond, C 1-36 Alkylene group, -(CH2) y1 -(O) y2 - (wherein y1 is an integer of 1 to 200, for example, an integer of 2 to 100, 5 to 100, or 10 to 50, and y2 is an integer of 1 to 100, for example, an integer of 2 to 50, 3 to 30, or 5 to 10), or -(CH2) y3 -phenylene-(CH2) y4 - (wherein y3 is an integer of 0 to 6, for example, an integer of 1 to 6, and y4 is an integer of 0 to 6, for example, an integer of 1 to 6). 1-36 The alkylene group may be straight-chain or branched, but is preferably straight-chain. 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.

[0024] In one embodiment, R A2is preferably CF3O-, CF3NH-, or (CF3)2N-, more preferably CF3O-.

[0025] R A3 is a monovalent group having a hydrogen atom or CF3-, CF3O-, CF3NH-, CF3CH2NH-, (CF3)2N-, (CF3CH2)2N-, CF3S-, CF3C(=O)-, CF3CH2C(=O)-, CF3C(=O)O-, CF3CH2OC(=O)-, CF3CONH-, CF3CH2CONH-, CF3NHCO-, CF3CH2NHCO-, CF3CON(CF3)-, CF3CH2CON(CF3)-, CF3CON(CH2CF3)-, CF3CH2CON(CH2CF3)-, (CF3)2NCO-, or (CF3CH2)2NCO-.

[0026] In one embodiment, R A3 is a hydrogen atom.

[0027] In another embodiment, R A3 is a monovalent group having CF3-, CF3O-, CF3NH-, CF3CH2NH-, (CF3)2N-, (CF3CH2)2N-, CF3S-, CF3C(=O)-, CF3CH2C(=O)-, CF3C(=O)O-, CF3CH2OC(=O)-, CF3CONH-, CF3CH2CONH-, CF3NHCO-, CF3CH2NHCO-, CF3CON(CF3)-, CF3CH2CON(CF3)-, CF3CON(CH2CF3)-, CF3CH2CON(CH2CF3)-, (CF3)2NCO-, or (CF3CH2)2NCO-.

[0028] R A3The monovalent group in may be preferably CF3O-, CF3NH-, CF3CH2NH-, (CF3)2N-, (CF3CH2)2N-, CF3S-, CF3C(=O)-, CF3CH2C(=O)-, CF3C(=O)O-, CF3CH2OC(=O)-, CF3CONH-, CF3CH2CONH-, CF3NHCO-, CF3CH2NHCO-, CF3CON(CF3)-, CF3CH2CON(CF3)-, CF3CON(CH2CF3)-, CF3CH2CON(CH2CF3)-, (CF3)2NCO-, or a monovalent group having (CF3CH2)2NCO-, more preferably a hydrogen atom, or a monovalent group having CF3O-, CF3NH-, or (CF3)2N-.

[0029] R A3 The monovalent group in R A3’ -X A3 - [In formula: R A3’ are CF3-, CF3O-, CF3NH-, CF3CH2NH-, (CF3)2N-, (CF3CH2)2N-, CF3S-, CF3C(=O)-, CF3CH2C(=O)-, CF3C(=O)O-, CF3CH2OC(=O)-, CF3CONH-, CF3CH2CONH-, CF3NHCO-, CF3CH2NHCO-, CF3CON(CF3)-, CF3CH2CON(CF3)-, CF3CON( CHCF)—, CFCHCON(CHCF)—, (CF)NCO—, or (CFCH)NCO—, preferably CFO—, CFNH—, (CF)N—, CFS—, CFC(═O)—, CFC(═O)O—, CFOC(═O)—, CFCONH—, or CFCON(CF)—, more preferably CFO—, CFNH—, or (CF)N—; X A3 is a single bond or a divalent group. It can be a group represented by the following formula:

[0030] X A3 is preferably a single bond, C 1-36 Alkylene group, -(CH2)y1 -(O) y2 - (wherein y1 is an integer of 1 to 200, for example, an integer of 2 to 100, 5 to 100, or 10 to 50, and y2 is an integer of 1 to 100, for example, an integer of 2 to 50, 3 to 30, or 5 to 10), or -(CH2) y3 -phenylene-(CH2) y4 - (wherein y3 is an integer of 0 to 6, for example, an integer of 1 to 6, and y4 is an integer of 0 to 6, for example, an integer of 1 to 6). 1-36 The alkylene group may be straight-chain or branched, but is preferably straight-chain. 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.

[0031] In one embodiment, a1 is an integer of 0-6.

[0032] In one embodiment, b1 is an integer of 0-30.

[0033] In one embodiment, c1 is an integer of 0-10, and in another embodiment, c1 is an integer of 0-3.

[0034] In one embodiment, d1 is 0 or 1.

[0035] In one embodiment, e1 is 1; in another embodiment, e1 is 2.

[0036] In one embodiment, f1 is 0 or 1.

[0037] In one embodiment, e1 is 1 or 2, d1 is 0 or 1, a1 is an integer of 0 to 200, b1 is an integer of 0 to 200, and c1 is an integer of 0 to 10. The repeating units enclosed in parentheses and marked with the symbols a1, b1, c1, and d1 may be present in any order.

[0038] In one embodiment, e1 is 1 or 2, d1 is 0 or 1, a1 is an integer of 0 to 6, b1 is an integer of 0 to 30, and c1 is an integer of 0 to 3. The repeating units enclosed in parentheses and marked with the symbols a1, b1, c1, and d1 may be present in any order.

[0039] In one embodiment, X B teeth, -(CFH) a1 -(CH2) b1 -(O) c1 - [In formula: a1 is an integer of 0 to 200, preferably an integer of 0 to 6, b1 is an integer of 0 to 200, preferably an integer of 0 to 30, c1 is an integer of 0 to 10, preferably an integer of 0 to 3, The repeating units enclosed in parentheses and designated by the symbols a1, b1, and c1 may occur in any order.] It is a group represented by the formula:

[0040] In one embodiment, X B is -(C(R A2 ) e1 H 2-e1 ) d1 -(CH2) b1 R is a group represented by the formula A2 , b1, d1 and e1 have the same meanings as above.

[0041] In one embodiment, X B teeth, -(CH2) b1 - [In the formula, b1 is an integer of 0 to 36, preferably an integer of 0 to 30, and in one embodiment, more preferably an integer of 1 to 9, and in another embodiment, more preferably an integer of 10 to 30, for example, an integer of 10 to 25.] It is a group represented by the formula:

[0042] In one embodiment, X B is -(CR A2 e1 H 2-e1 )d1 -O-(CH2) b1 R is a group represented by the formula A2 , a1, b1, and e1 have the same meanings as above.

[0043] In one embodiment, X B is -O-(CH2) b1 b1 is a group represented by the formula: -. b1 has the same meaning as above. Preferably, b1 is an integer of 0 to 30.

[0044] In one embodiment, X B is -(CR A2 e1 H 2-e1 ) d1 -(CH2) b1 R is a group represented by -O-. A2 , e1, b1, and d1 have the same meanings as above.

[0045] In one embodiment, X B is -(CH2) b1 It is a group represented by -O-. b1 has the same meaning as above. In one embodiment, b1 is an integer of 0 to 30, and in another embodiment, b1 is an integer of 0 to 10.

[0046] In one embodiment, X B is -(CH2) b10 -O-(CH2) b10 - is a group represented by the formula: Each b10 is independently an integer of 0 to 200, provided that the sum of two b10's is an integer of 0 to 200.

[0047] In one embodiment, X B is a group containing a divalent siloxane group. B contains a structure in which two silicon atoms are bonded via oxygen (-Si-O-Si-).

[0048] In such embodiments, X B is more preferably -(CH2) g1 -R S -Si(R 5)2-(CH2) g1 - [In formula: Each g1 is independently an integer of 0 to 30, R S is expressed by the following formula: [ka] (In the formula: R 3 are each independently a single bond, C 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 -, or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 - and R 4 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 -, or -R 9 -R 6 -R 9 -R7 -R 9 -R 6 -R 9 - and R 6 are each independently 1-6 is an alkylene group, R 7 each independently represents an optionally substituted phenylene group or naphthylene group, R 8 are each independently 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 repeating units enclosed in parentheses with x, y, or z may occur in any order in the formula. is a group represented by the following formula: It is a group represented by the formula:

[0049] Each g1 is independently an integer of 0 to 30. g1 is, for example, an integer of 1 to 30, an integer of 1 to 10, or an integer of 1 to 3. In one embodiment, g1 is 0.

[0050] R 3 are each independently a single bond, C 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 -, preferably C 1-12 Alkylene group, or -R 6 -OR 6 -It is.

[0051] In one embodiment, R 3 are each independently a single bond.

[0052] In another embodiment, 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 -, preferably C 1-12 Alkylene group, or -R 6 -OR 6 -It is.

[0053] R 4 are each independently 1-12 Alkylene group, -R 6 -OR 6 -, -R 8 -R 7 -R8 -, -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.

[0054] In one embodiment, R 4 are each independently 1-12 Alkylene group, or -R 6 -OR 6 -It is.

[0055] 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.

[0056] In one embodiment, R 3 are each independently 1-12 Alkylene group, or -R 6 -OR 6 - and R4 are each independently 1-12 Alkylene group, or -R 6 -OR 6 -It is.

[0057] In another embodiment, R 3 are each independently 1-12 Alkylene group, or -R 6 -OR 6 - and R 4 are each independently -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 -, or -R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 -It is.

[0058] Above C 1-12 The alkylene group may be a straight chain or a branched chain. 1-12 The alkylene group is preferably straight-chain.

[0059] Above C 1-12 The alkylene group is preferably C 2-8 Alkylene groups, more preferably C 2-6 It is an alkylene group.

[0060] R 6 are each independently 1-6 The above C is an alkylene group. 1-6 The alkylene group may be a straight chain or a branched chain. 1-6 The alkylene group is preferably straight-chain.

[0061] Above C 1-6 The alkylene group is preferably C 2-4 Alkylene groups, more preferably C 2-3 It is an alkylene group.

[0062] In a preferred embodiment, multiple R 6 In a group containing 6 are the same group.

[0063] R 7 are each independently an optionally substituted arylene group.

[0064] In one embodiment, R 7 are each independently [ka] is.

[0065] In one embodiment, R 7 is a phenylene group.

[0066] In another embodiment, R 7 is a naphthylene group.

[0067] 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.

[0068] In one embodiment, the phenylene group and naphthylene group may have a substituent. The number of 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.

[0069] The substituents on the arylene group are each independently -R 41 -R 42 is.

[0070] R 41is a single bond, an oxygen atom, or a sulfur atom, preferably a single bond or an oxygen atom, more preferably an oxygen atom.

[0071] R 42 is C optionally substituted with halogen 1-12 Alkyl group, -(OR 43 ) p , -R 44 -R 45 , -R 44 -OR 46 is.

[0072] The halogen is fluorine, chlorine, bromine or iodine, preferably fluorine.

[0073] R 42 C in 1-12 The alkyl group may be straight-chain or branched.

[0074] R 43 is C 1-6 Alkylene group, preferably C 2-4 It is an alkylene group. Such an alkylene group may be a straight chain or a branched chain.

[0075] 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.

[0076] R 45 is -CH=CH2, or -OCOCH=CH2.

[0077] R 46 is a hydrogen atom or C 1-6 The alkyl group may be a straight chain or a branched chain. 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.

[0078] R 8 are each independently a single bond or C 1-6 It is an alkylene group. 1-6 The alkylene group may be a straight chain or a branched chain.

[0079] In one embodiment, R 8 is a single bond.

[0080] In another embodiment, R 8 is C 1-6 It is an alkylene group.

[0081] R 9 are each independently a single bond or an oxygen atom.

[0082] In one embodiment, R 9 is a single bond.

[0083] In another embodiment, R 9 is an oxygen atom.

[0084] R 5 are each independently a hydrocarbon group. Such hydrocarbon groups may be substituted.

[0085] 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.

[0086] R 5 are each independently preferably C optionally substituted by a halogen atom. 1-18 an alkyl or aryl group, more preferably C 1-18 It is an alkyl group or an aryl group.

[0087] Above C 1-18 The alkyl group may be a straight chain or a branched chain, but is preferably a straight chain. 1-18 The alkyl group is preferably C1-10 Alkyl groups, more preferably C 1-6 alkyl group, more preferably C 1-4 It is preferably an alkyl group, and even more preferably a methyl group.

[0088] The aryl group is preferably a phenyl group.

[0089] 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.

[0090] In another embodiment, R 5 is a phenyl group.

[0091] In another embodiment, R 5 are each independently a methyl group or a phenyl group, preferably a methyl group.

[0092] 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.

[0093] In one embodiment, x is 0.

[0094] 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 even more preferably an integer of 10 to 30.

[0095] y 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.

[0096] In one embodiment, y is 0.

[0097] 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 even more preferably an integer of 10 to 30.

[0098] z 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.

[0099] In one embodiment, z is 0.

[0100] 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 even more preferably an integer of 10 to 30.

[0101] In one embodiment, y is 0 and z is 0.

[0102] The divalent siloxane-containing group may be a random polymer or a block polymer.

[0103] In one embodiment, X B is -(CH2) c11 -(O(CH2) c12 ) c13 - is a group represented by the formula:

[0104] c11 is an integer of 0 to 200, c12 is an integer of 0 to 200, and c13 is an integer of 0 to 200. B The number of carbon atoms contained in is an integer of 0 to 200. For example, c12 and c13 are each an integer of 1 or more.

[0105] For example, c11 is an integer from 1 to 4, c12 is an integer from 1 to 10, and c13 is an integer from 1 to 150.

[0106] In one embodiment, the X B The number of carbon atoms contained in is an integer of 1 to 150.

[0107] In one embodiment, c11 is an integer of 0 to 20, c12 is an integer of 1 to 6, and c13 is an integer of 0 to 150, preferably, c13 is an integer of 1 to 50, and the X B The number of carbon atoms contained in is an integer of 1 to 150.

[0108] In one embodiment, c11 is an integer of 1 to 30, c12 is an integer of 1 to 3, and c13 is an integer of 2 to 150, for example, an integer of 2 to 50.

[0109] α1 is an integer of 1 to 9, and α2 is an integer of 1 to 9. These α1 and α2 are X A The sum of α1 and α2 can vary depending on the valence of X A For example, X A When X is a decavalent organic group, the sum of α1 and α2 is 10, and for example, α1 can be 9 and α2 can be 1, α1 can be 5 and α2 can be 5, or α1 can be 1 and α2 can be 9. A When is a divalent organic group, α1 and α2 are 1.

[0110] X A is a single bond, an oxygen atom, or a divalent to decavalent organic group. A is Rf on the left 1 , and the right side is R Si are respectively connected to

[0111] In one embodiment, X A Rf binds to 1 If the element in is an oxygen atom, Rf 1 X binds to A The element inside is not oxygen.

[0112] Above X A is Rf 1 A part (R) that provides bonding ability between the part and the substrate Si Therefore, the X A may be a single bond, an oxygen atom, or any organic group, so long as the compound represented by formula (1) can exist stably.

[0113] Above X A are each independently a fluorine atom, C 1-3 Alkyl groups and C 1-3 Fluoroalkyl groups (preferably C 1-3 In one embodiment, X may be substituted with one or more substituents selected from the group consisting of: A is non-substituted.

[0114] Above X A The divalent to decavalent organic group in the formula (I) is preferably a divalent to octavalent organic group. In one embodiment, the divalent to decavalent organic group is preferably a divalent to tetravalent organic group, more preferably a divalent organic group. In another embodiment, the divalent to decavalent organic group is preferably a trivalent to octavalent organic group, more preferably a trivalent to hexavalent organic group.

[0115] In one embodiment, X A is a single bond.

[0116] In one embodiment, X A is an oxygen atom.

[0117] In one embodiment, X A is a divalent to decavalent organic group.

[0118] In one embodiment, X A is a single bond or a divalent organic group, and α1 and α2 are 1.

[0119] In one embodiment, the X A is a divalent organic group, and α1 and α2 are 1.

[0120] In one embodiment, X A is a trivalent to hexavalent organic group, α1 is 1, and α2 is 2 to 5.

[0121] In one embodiment, X A is a trivalent organic group, α1 is 1, and α2 is 2.

[0122] In one embodiment, X A is a trivalent organic group, α1 is 2, and α2 is 1.

[0123] In one embodiment, the X A is a single bond, -(X 52 ) l5 - or the formula (X A1 ): [ka] It is expressed as:

[0124] Above X 52 each independently represents -O-, -S-, o-, m- or p-phenylene group, -CO-, -C(O)O-, -OC(O)-, or -CONR 54 -, -NR 54 CO-, -O-CONR 54 -, -NR 54 CO-O-, -NR 54 CONR 54 -, -NR 54 - and -(CH2) n5 - is a group selected from

[0125] Above R 54 are each independently a hydrogen atom or a monovalent organic group, and are preferably a hydrogen atom, a phenyl group, or C 1-6 It is an alkyl group (preferably a methyl group) or an oxyalkylene-containing group having 1 to 10 carbon atoms.

[0126] The above n5s are each independently an integer of 1 to 200. n5 is, for example, an integer of 1 to 30, specifically an integer of 1 to 20, more specifically an integer of 1 to 15, an integer of 1 to 10, or an integer of 1 to 6, for example, an integer of 1 to 3. In one embodiment, n5 is an integer of 10 to 200, for example, an integer of 10 to 30. In one embodiment, n5 is an integer of 1 to 9. In one embodiment, n5 is an integer of 10 to 30. In one embodiment, n5 is an integer of 16 to 26.

[0127] The oxyalkylene-containing group having 1 to 10 carbon atoms is —OC 1-10 alkylene-containing groups, such as -R 55 -(-OC 1-10 alkylene) n -R 56 (In the formula, R 55 is a single bond or a divalent organic group, preferably C 1-6 is an alkylene group, n is an integer of any value, preferably an integer of 2 to 10, and R 56 is a hydrogen atom or a monovalent organic group, preferably C 1-6 It is an alkyl group.) The alkylene group may be a straight chain or a branched chain.

[0128] Above X a is a single bond or a divalent linking group directly bonded to the isocyanuric ring. a is preferably a single bond, an alkylene group, or a divalent group containing at least one bond selected from the group consisting of an ether bond, an ester bond, an amide bond, and a sulfide bond, and more preferably a single bond, an alkylene group having 1 to 10 carbon atoms, or a divalent hydrocarbon group having 1 to 10 carbon atoms and containing at least one bond selected from the group consisting of an ether bond, an ester bond, an amide bond, and a sulfide bond. a The left side is attached to the isocyanuric ring.

[0129] 1-2 X a The group having Rf 1 1 to 2 X a The group having R Si The X a The total number of groups having is 3.

[0130] Above X a As the formula: -(CX 121 X 122 ) x1 -(X a11 ) y1 -(CX 123 X 124 ) z1 - [In the formula, X 121 ~X 124 are each independently H, OH, or -OSi(OR 121 )3 (wherein three R 121 are each independently an alkyl group having 1 to 4 carbon atoms, X a11 -C(=O)NH-, -NHC(=O)-, -O-, -C(=O)O-, -OC(=O)-, -OC(=O)O-, -NHC(=O)NH-, -NR 122 -, -C(=O)-NR 122 -, -NR 122 -C(=O)- or S (the left side of each bond is CX 121 X 122 ), R 122 is C 1-6 hydrocarbon chains, preferably C 1-6 is an alkyl group, x1 is an integer of 0 to 10, y1 is 0 or 1, and z1 is an integer of 1 to 10. A group represented by the following formula is more preferred.

[0131] Above X a11 is preferably —O— or —C(═O)O—.

[0132] Above X a is preferably a group represented by the following formula: -(CH2) m12 -O-(CH2) m13 - (In the formula, m12 is an integer of 1 to 10, and m13 is an integer of 1 to 10.) -(CH2) m15 -O-CH2CH(OH)-(CH2) m16 - (In the formula, m15 is an integer of 1 to 10, and m16 is an integer of 1 to 10.) -(CH2) m18 - (In the formula, m18 is an integer of 1 to 10.) or -(CH2)m20 -O-CH2CH(OSi(OCH3)3)-(CH2) m21 - (In the formula, m20 is an integer of 1 to 10, and m21 is an integer of 1 to 10.)

[0133] Above X a Examples of the alkyl group include, but are not limited to, -CH2-, -C2H4-, -C3H6-, -C4H8-, -C4H8-O-CH2-, -CO-O-CH2-CH(OH)-CH2-, -S-, and -NR 121 -, -(CH2) m22 -C(=O)-O-(CH2) m23 -, -(CH2) m22 -OC(=O)-(CH2) m23 -, -(CH2) m22 -C(=O)-NR 121 -(CH2) m23 -, -(CH2) m22 -NR 121 -C(=O)-(CH2) m23 -CH2OCH2CH(OSi(OCH3)3)CH2- (R in the formula 121 is C 1-6 is a hydrocarbon chain, m22 is an integer of 1 to 10, and m23 is an integer of 1 to 10. etc.

[0134] Above X A When is a single bond, an oxygen atom, or a divalent organic group, formula (1) is represented by the following formula (1'). [ka]

[0135] Above X A is preferably a single bond or a divalent organic group.

[0136] In one embodiment, the X A are each independently -(X 52 ) l5 -R 52 - is expressed as R above. 52is a single bond, -(CH2) t5 - or an o-, m- or p-phenylene group, preferably -(CH2) t5 The above t5 is an integer of 1 to 30, preferably an integer of 2 to 20, more preferably an integer of 2 to 12, and even more preferably an integer of 2 to 3. Here, R 52 (Typically R 52 hydrogen atoms) are fluorine atoms, C 1-3 Alkyl groups and C 1-3 In a preferred embodiment, R 52 is not substituted with these groups.

[0137] For example, the above X A As, each independently, single bond, -CONR 54 -(CH2) n5 -, -(CH2) n5 -CONR 54 -(CH2) n5 -, -(CH2) n5 -CONR 54 -, -(CH2) n5 -, -OC(=O)-(CH2) n5 -, -(CH2) n5 -OC(=O)-(CH2) n5 - -C(=O)O-(CH2) n5 -, -(CH2) n5 -C(=O)O-(CH2) n5 - -C(=O)-(CH2) n5 -, -(CH2) n5 -C(=O)-(CH2) n5 - Examples include:

[0138] In one embodiment, the X AAs, each independently, single bond, -CONR 54 -(CH2) n5 -, -OC(=O)-(CH2) n5 -, -C(=O)-(CH2) n5 -, Examples include:

[0139] In one embodiment, the X 52 each independently represents an -S-, o-, m-, or p-phenylene group, -CO-, -C(O)O-, -OC(O)-, or -CONR 54 -, -O-CONR 54 -, -NR 54 CO-, -O-CONR 54 -, -NR 54 CO-O-, and -NR 54 - is a group selected from

[0140] In one embodiment, the X 52 is -(CH2) n5 -CONR 53 -It is.

[0141] In one embodiment, the X A teeth, -(p-phenylene) v1 -(CH2) v2 -R 57 v3 -(CH2) v4 - [In formula: R 57 is -CONH-, -NHCO-, -COO-, or -O-, v1 is 0 or 1, v2 is an integer between 0 and 20, v3 is 0 or 1, v4 is an integer between 2 and 20. It is a compound represented by the formula:

[0142] In a preferred embodiment, the X A teeth, -(p-phenylene) v1 -(CH2) v2 -R 57 v3 -(CH2) v4 - [In formula: R 57 is -NHCO- or -COO-, v1 is 1, v2 is an integer from 0 to 3, v3 is 1, v4 is an integer between 8 and 16. It is a compound represented by the formula:

[0143] In a preferred embodiment, the X A teeth, -(CH2) v2 -CONH-(CH2) v4 - [In formula: v2 is an integer between 10 and 22, v4 is an integer between 1 and 3. It is a compound represented by the formula:

[0144] In one embodiment, the X A teeth, -(CH2) v2 -O-(CH2) v4 - [In formula: v2 is an integer from 1 to 3, v4 is an integer between 10 and 22. It is a compound represented by the formula:

[0145] In one embodiment, the X A is a group represented by the following formula: [ka]

[0146] R Si is a monovalent group containing a Si atom to which a hydroxyl group or a hydrolyzable group is bonded.

[0147] R Si is preferably a group represented by formula (S1), (S2), (S3), (S4) or (S5). [ka]

[0148] R 11 are each independently a hydroxyl group or a hydrolyzable group.

[0149] R 11 are preferably each independently a hydrolyzable group.

[0150] R 12 are each independently a monovalent organic group. 12 does not contain a hydrolyzable group.

[0151] R 12 In the formula, the monovalent organic group is preferably C 1-20 alkyl group, more preferably C 1-6 It is preferably an alkyl group, more preferably a methyl group.

[0152] 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.

[0153] n1 is (SiR 11 n1 R 12 3-n1 ) units are each independently an integer of preferably 1 to 3, more preferably 2 to 3, and even more preferably 3.

[0154] 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 are each independently a single bond or C 1-20 is an alkylene group, and x is 0 or 1. 1-20 The alkylene group may be straight-chain or branched, but is preferably straight-chain. 1-20 The alkylene group is preferably C 1-10 Alkylene groups, more preferably C 1-6 Alkylene groups, more preferably C 1-3 It is an alkylene group.

[0155] In one embodiment, X 11 are each independently -C 1-6 Alkylene-OC 1-6 Alkylene- or -OC 1-6 It is alkylene.

[0156] In a preferred embodiment, X 11 are each independently a single bond or a linear C 1-6 Alkylene group, preferably a single bond or a straight chain C 1-3 Alkylene group, more preferably a single bond or a straight chain C 1-2 It is preferably a linear C alkylene group. 1-2 It is an alkylene group.

[0157] R 13 are each independently a hydrogen atom or a monovalent organic group. Such a monovalent organic group is preferably C 1-20 It is an alkyl group.

[0158] 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 1-3It is an alkyl group, preferably a hydrogen atom or a methyl group.

[0159] R 15 are each independently a single bond, an oxygen atom, or C 1-6 Alkylene group or C 1-6 It is an alkyleneoxy group.

[0160] In one embodiment, R 15 are each independently an oxygen atom, C 1-6 Alkylene group or C 1-6 It is an alkyleneoxy group.

[0161] In a preferred embodiment, R 15 is a single bond.

[0162] Each t is independently an integer of 2 or greater.

[0163] In a preferred embodiment, each t is independently an integer of 2 to 10, preferably an integer of 2 to 6.

[0164] R 14 are each independently a hydrogen atom, a halogen atom or -X 11 -SiR 11 n1 R 12 3-n1 Such a halogen atom is preferably an iodine atom, a chlorine atom, or a fluorine atom, more preferably a fluorine atom. In a preferred embodiment, R 14 is a hydrogen atom.

[0165] 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 repeating units enclosed in parentheses with t1 and t2 may occur in any order in the formula.]

[0166] 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 defined as in formula (S1) above.

[0167] In a preferred embodiment, in formula (S2), -SiR 11 n1 R 12 3-n1 The Si atoms do not form siloxane bonds.

[0168] R a1 are each independently -Z 1 -SiR 21 p1 R 22 q1 R 23 r1 is.

[0169] Above Z 1 are each independently an oxygen atom or a divalent organic group. 1 The structure written as 21 p1 R 22 q1 R 23 r1 )

[0170] In a preferred embodiment, Z 1 is a divalent organic group.

[0171] 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 (Si-Z) is bonded. 1 —Si) does not contain a siloxane bond.

[0172] Above Z 1 is preferably C 1-30 Alkylene group, -(CH2) z1 -O-(CH2) z2 - (wherein z1 is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6, and z2 is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6), or -(CH2) z3 -phenylene-(CH2) z4 - (wherein z3 is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6, and z4 is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6). 1-30 The alkylene group may be straight-chain or branched, but is preferably straight-chain. These groups may contain, for example, fluorine atoms, C 1-30 Alkyl group, C 2-30 Alkenyl groups, and C 2-30 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.

[0173] In a preferred embodiment, Z 1 is C 1-6 Alkylene group or -(CH2) z3 -phenylene-(CH2) z4 -, preferably -phenylene-(CH2) z4 -It is.

[0174] In another preferred embodiment, the Z 1 is C 1-3 In one embodiment, Z is an alkylene group. 1 can be -CH2CH2CH2-. In another embodiment, Z 1 can be -CH2CH2-. In another embodiment, Z1 can be -CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2-.

[0175] R 21 are each independently -Z 1’ -SiR 21’ p1’ R 22’ q1’ R 23’ r1’ is.

[0176] Above Z 1’ are each independently an oxygen atom or a divalent organic group. 1’ The structure written as 21’ p1’ R 22’ q1’ R 23’ r1’ )

[0177] In a preferred embodiment, Z 1’ is a divalent organic group.

[0178] 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 (Si-Z) is bonded. 1’ —Si) does not contain a siloxane bond.

[0179] Above Z 1’ is preferably C 1-30 Alkylene group, -(CH2) z1’ -O-(CH2) z2’ - (wherein z1' is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6, and z2' is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6), or -(CH2) z3’ -phenylene-(CH2) z4’- (wherein z3' is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6, and z4' is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6). 1-30 The alkylene group may be straight-chain or branched, but is preferably straight-chain. These groups may contain, for example, fluorine atoms, C 1-30 Alkyl group, C 2-30 Alkenyl groups, and C 2-30 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.

[0180] In a preferred embodiment, Z 1’ is C 1-6 Alkylene group or -(CH2) z3’ -phenylene-(CH2) z4’ -, preferably -phenylene-(CH2) z4’ -It is.

[0181] In another preferred embodiment, the Z 1’ is C 1-3 In one embodiment, Z is an alkylene group. 1’ can be -CH2CH2CH2-. In another embodiment, Z 1’ can be -CH2CH2-. In another embodiment, Z 1’ can be -CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2-.

[0182] R 21’ are each independently -Z 1” -SiR 22” q1” R 23” r1” is.

[0183] Z 1” are each independently an oxygen atom or a divalent organic group. 1” The structure written as 22” q1” R 23” r1”)

[0184] In a preferred embodiment, Z 1” is a divalent organic group.

[0185] 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 (Si-Z) is bonded. 1” —Si) does not contain a siloxane bond.

[0186] Z 1” is preferably C 1-30 Alkylene group, -(CH2) z1” -O-(CH2) z2” - (wherein z1" is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6, and z2" is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6), or -(CH2) z3” -phenylene-(CH2) z4” - (wherein z3" is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6, and z4" is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6). 1-30 The alkylene group may be straight-chain or branched, but is preferably straight-chain. These groups may contain, for example, fluorine atoms, C 1-30 Alkyl group, C 2-30 Alkenyl groups, and C 2-30 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.

[0187] In a preferred embodiment, Z 1” is C 1-6 Alkylene group or -(CH2) z3” -phenylene-(CH2) z4” -, preferably -phenylene-(CH2) z4” -It is. Z 1” is such a group, the light resistance, particularly the ultraviolet resistance, can be improved.

[0188] In another preferred embodiment, the Z 1” is C 1-3 In one embodiment, Z is an alkylene group. 1” can be -CH2CH2CH2-. In another embodiment, Z 1” can be -CH2CH2-. In another embodiment, Z 1” can be -CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2-.

[0189] R 22” are each independently a hydroxyl group or a hydrolyzable group.

[0190] R 22” are preferably each independently a hydrolyzable group.

[0191] R 23” are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above-mentioned hydrolyzable groups.

[0192] R 23” In the formula, the monovalent organic group is preferably C 1-20 alkyl group, more preferably C 1-6 It is preferably an alkyl group, more preferably a methyl group.

[0193] 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 (SiR 22” q1” R 23” r1” ) units, it is 3.

[0194] q1” is (SiR 22” q1” R 23” r1” ) units are each independently an integer of preferably 1 to 3, more preferably 2 to 3, and even more preferably 3.

[0195] R 22’ are each independently a hydroxyl group or a hydrolyzable group.

[0196] R 22’ are preferably each independently a hydrolyzable group.

[0197] R 23’ are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above-mentioned hydrolyzable groups.

[0198] R 23’ In the formula, the monovalent organic group is preferably C 1-20 alkyl group, more preferably C 1-6 It is preferably an alkyl group, more preferably a methyl group.

[0199] 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 p', q1', and r1' is (SiR 21’ p1’ R 22’ q1’ R 23’ r1’ ) units, it is 3.

[0200] In one embodiment, p1' is 0.

[0201] 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.

[0202] In one embodiment, q1′ is (SiR 21’ p1’ R 22’ q1’ R 23’ r1’) units are each independently an integer of 1 to 3, preferably an integer of 2 or 3, and more preferably 3.

[0203] In one embodiment, p1' is 0 and q1' is (SiR 21’ p1’ R 22’ q1’ R 23’ r1’ ) units are each independently an integer of 1 to 3, preferably an integer of 2 to 3, and more preferably 3.

[0204] R 22 are each independently a hydroxyl group or a hydrolyzable group.

[0205] R 22 are preferably each independently a hydrolyzable group.

[0206] R 23 are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above-mentioned hydrolyzable groups.

[0207] R 23 In the formula, the monovalent organic group is preferably C 1-20 alkyl group, more preferably C 1-6 It is preferably an alkyl group, more preferably a methyl group.

[0208] 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 p1, q1, and r1 is (SiR 21 p1 R 22 q1 R 23 r1 ) units, it is 3.

[0209] In one embodiment, p1 is 0.

[0210] In one embodiment, p1 is (SiR 21p1 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.

[0211] In one embodiment, q1 is (SiR 21 p1 R 22 q1 R 23 r1 ) units are each independently an integer of 1 to 3, preferably an integer of 2 or 3, and more preferably 3.

[0212] In one embodiment, p1 is 0 and q1 is (SiR 21 p1 R 22 q1 R 23 r1 ) units are each independently an integer of 1 to 3, preferably an integer of 2 to 3, and more preferably 3.

[0213] R b1 are each independently a hydroxyl group or a hydrolyzable group.

[0214] R b1 are preferably each independently a hydrolyzable group.

[0215] R c1 are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above-mentioned hydrolyzable groups.

[0216] R c1 In the formula, the monovalent organic group is preferably C 1-20 alkyl group, more preferably C 1-6 It is preferably an alkyl group, more preferably a methyl group.

[0217] 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.

[0218] 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, more preferably 3. In a preferred embodiment, k1 is 3.

[0219] In formula (S3), there are at least two Si atoms to which hydroxyl groups or hydrolyzable groups are bonded.

[0220] In a preferred embodiment, there are at least two Si atoms in the terminal portion of formula (S3) to which hydroxyl groups or hydrolyzable groups are bonded.

[0221] 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” R 23” r1”(wherein q1″ is an integer of 1 to 3, preferably 2 or 3, more preferably 3, and r1″ is an integer of 0 to 2). Z 1 , Z 1’ , Z 1” , R 22 , R 23 , R 22’ , R 23’ , R 22” , and R 23” has the same meaning as above.

[0222] In a preferred embodiment, in formula (S3), R 21’ When present, at least one, preferably all, R 21’ In the formula, q1″ is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.

[0223] In a preferred embodiment, in formula (S3), R 21 When present, at least one, preferably all, R 21 In the formula (I), p1' is 0, and q1' is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.

[0224] In a preferred embodiment, in formula (S3), R a1 When present, at least one, preferably all, R a1 In the formula (I), p1 is 0, and q1 is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.

[0225] 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.

[0226] R d1 are each independently -Z 2 -CR 31 p2 R 32 q2 R 33 r2 is.

[0227] Z 2 are each independently a single bond, an oxygen atom, or a divalent organic group. 2 The structure written as (CR 31 p2 R 32 q2 R 33 r2 )

[0228] In a preferred embodiment, Z 2 is a divalent organic group.

[0229] In a preferred embodiment, Z 2 does not contain siloxane bonds.

[0230] Z 2 is preferably C 1-30 Alkylene group, -(CH2) z5 -O-(CH2) z6 - (wherein z5 is an integer of 0 to 30, for example, an integer of 1 to 206, an integer of 0 to 6, or an integer of 1 to 6, and z6 is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6), or -(CH2) z7 -phenylene-(CH2) z8 - (wherein z7 is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6, and z8 is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6). 1-30 The alkylene group may be straight-chain or branched, but is preferably straight-chain. These groups may contain, for example, fluorine atoms, C 1-30 Alkyl group, C 2-30 Alkenyl groups, and C 2-30 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.

[0231] In a preferred embodiment, Z 2 is C 1-6 Alkylene group or -(CH2) z7 -phenylene-(CH2) z8-, preferably -phenylene-(CH2) z8 -It is. Z 2 is such a group, the light resistance, particularly the ultraviolet resistance, can be improved.

[0232] In another preferred embodiment, the Z 2 is C 1-3 In one embodiment, Z is an alkylene group. 2 can be -CH2CH2CH2-. In another embodiment, Z 2 can be -CH2CH2-. In another embodiment, Z 2 can be -CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2-.

[0233] R 31 are each independently -Z 2’ -CR 32’ q2’ R 33’ r2’ is.

[0234] Z 2’ are each independently a single bond, an oxygen atom, or a divalent organic group. 2’ The structure written as (CR 32’ q2’ R 33’ r2’ )

[0235] In a preferred embodiment, Z 2’ does not contain siloxane bonds.

[0236] Z 2’ is preferably C 1-30 Alkylene group, -(CH2) z5’ -O-(CH2) z6’ - (wherein z5' is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6, and z6' is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6), or -(CH2) z7’ -phenylene-(CH2) z8’- (wherein z7' is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6, and z8' is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6). 1-30 The alkylene group may be straight-chain or branched, but is preferably straight-chain. These groups may contain, for example, fluorine atoms, C 1-30 Alkyl group, C 2-30 Alkenyl groups, and C 2-30 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.

[0237] In a preferred embodiment, Z 2’ is C 1-6 Alkylene group or -(CH2) z7’ -phenylene-(CH2) z8’ -, preferably -phenylene-(CH2) z8’ -It is. Z 2’ is such a group, the light resistance, particularly the ultraviolet resistance, can be improved.

[0238] In another preferred embodiment, the Z 2’ is C 1-3 In one embodiment, Z is an alkylene group. 2’ can be -CH2CH2CH2-. In another embodiment, Z 2’ can be -CH2CH2-. In another embodiment, Z 2’ can be -CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2-.

[0239] R 32’ are each independently -Z 3 -SiR 34 n2 R 35 3-n2 is.

[0240] Z 3 are each independently a single bond, an oxygen atom, or a divalent organic group. 3 The structure written as34 n2 R 35 3-n2 )

[0241] In one embodiment, Z 3 is an oxygen atom.

[0242] In one embodiment, Z 3 is a divalent organic group.

[0243] In a preferred embodiment, Z 3 does not contain siloxane bonds.

[0244] Z 3 is preferably C 1-30 Alkylene group, -(CH2) z5” -O-(CH2) z6” - (wherein z5" is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6, and z6" is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6), or -(CH2) z7” -phenylene-(CH2) z8” - (wherein z7" is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6, and z8" is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6). 1-30 The alkylene group may be straight-chain or branched, but is preferably straight-chain. These groups may contain, for example, fluorine atoms, C 1-30 Alkyl group, C 2-30 Alkenyl groups, and C 2-30 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.

[0245] In a preferred embodiment, Z 3 is C 1-6 Alkylene group or -(CH2) z7” -phenylene-(CH2) z8” -, preferably -phenylene-(CH2) z8” -It is. Z 3is such a group, the light resistance, particularly the ultraviolet resistance, can be improved.

[0246] In another preferred embodiment, the Z 3 is C 1-3 In one embodiment, Z is an alkylene group. 3 can be -CH2CH2CH2-. In another embodiment, Z 3 can be -CH2CH2-. In another embodiment, Z 3 can be -CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2-.

[0247] R 34 are each independently a hydroxyl group or a hydrolyzable group.

[0248] R 34 are preferably each independently a hydrolyzable group.

[0249] R 35 are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above-mentioned hydrolyzable groups.

[0250] R 35 In the formula, the monovalent organic group is preferably C 1-20 alkyl group, more preferably C 1-6 It is preferably an alkyl group, more preferably a methyl group.

[0251] In the above formula, n2 is (SiR 34 n2 R 35 3-n2 ) units are each independently an integer of 0 to 3. However, in the terminal portion of formula (S4), n2 is 1 to 3 (SiR 34 n2 R 35 3-n2 In other words, at each terminal portion of formula (S4), there are at least two Si atoms to which a hydroxyl group or a hydrolyzable group is bonded.

[0252] n2 is (SiR 34 n2 R 35 3-n2 ) units are each independently an integer of preferably 1 to 3, more preferably 2 to 3, and even more preferably 3.

[0253] Above R 33’ are each independently a hydrogen atom, a hydroxyl group, or a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above-mentioned hydrolyzable groups.

[0254] Above R 33’ In the formula, 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), and more preferably C 1-20 alkyl group, more preferably C 1-6 An alkyl group, particularly preferably a methyl group.

[0255] In one embodiment, R 33’ is a hydroxyl group.

[0256] In another embodiment, R 33’ is a monovalent organic group, preferably C 1-20 alkyl group, more preferably C 1-6 It is an alkyl group.

[0257] The above q2's are each independently an integer of 0 to 3, and the above r2's are each independently an integer of 0 to 3. The sum of q2' and r2' is (CR 32’ q2’ R 33’ r2’ ) units, it is 3.

[0258] q2' is (CR 32’ q2’ R 33’ r2’ ) units are each independently an integer of preferably 1 to 3, more preferably 2 to 3, and even more preferably 3.

[0259] R 32 are each independently -Z 3 -SiR 34 n2 R 35 3-n2 It takes -Z 3 -SiR 34 n2 R 35 3-n2 is the above R 32’ This has the same meaning as the description in

[0260] 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-mentioned hydrolyzable groups.

[0261] R 33 In the formula, the monovalent organic group is preferably C 1-20 Alkyl group or -(C s H 2s ) t1 -(OC s H 2s ) t2 -H (wherein each s is independently 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), and more preferably C 1-20 alkyl group, more preferably C 1-6 An alkyl group, particularly preferably a methyl group.

[0262] In one embodiment, R 33 is a hydroxyl group.

[0263] In another embodiment, R 33 is a monovalent organic group, preferably C 1-20alkyl group, more preferably C 1-6 It is an alkyl group.

[0264] 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.

[0265] In one embodiment, p2 is 0.

[0266] 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.

[0267] In one embodiment, q2 is (CR 31 p2 R 32 q2 R 33 r2 ) units are each independently an integer of 1 to 3, preferably an integer of 2 or 3, and more preferably 3.

[0268] In one embodiment, p2 is 0 and q2 is (CR 31 p2 R 32 q2 R 33 r2 ) units are each independently an integer of 1 to 3, preferably an integer of 2 to 3, and more preferably 3.

[0269] Above R e1 are each independently -Z 3 -SiR 34 n2 R35 3-n2 It takes -Z 3 -SiR 34 n2 R 35 3-n2 is the above R 32’ This has the same meaning as the description in

[0270] Above 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-mentioned hydrolyzable groups.

[0271] Above R f1 In the formula, the monovalent organic group is preferably C 1-20 Alkyl group or -(C s H 2s ) t1 -(OC s H 2s ) t2 -H (wherein each s is independently 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), and more preferably C 1-20 alkyl group, more preferably C 1-6 An alkyl group, particularly preferably a methyl group.

[0272] In one embodiment, R f1 is a hydroxyl group.

[0273] In another embodiment, R f1 is a monovalent organic group, preferably C 1-20 alkyl group, more preferably C 1-6 It is an alkyl group.

[0274] The above k2's are each independently an integer of 0 to 3, the l2's are each independently an integer of 0 to 3, and the m2's are each independently an integer of 0 to 3. The sum of k2, l2, and m2 is (CR d1 k2 R e1 l2 Rf1 m2 ) units, it is 3.

[0275] 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 (S4) by two or more, for example, 2 to 27, preferably 2 to 9, more preferably 2 to 6, even more preferably 2 to 3, and particularly preferably 3.

[0276] In a preferred embodiment, in formula (S4), R 32’ When present, at least one, preferably all, R 32’ In the formula, n2 is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.

[0277] In a preferred embodiment, in formula (S4), R 32 When present, at least one, preferably all, R 32 In the formula, n2 is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.

[0278] In a preferred embodiment, in formula (S4), R e1 When present, at least one, preferably all, R a1 In the formula, n2 is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.

[0279] 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.

[0280] Above R g1 and R h1 are each independently -Z 4 -SiR 11 n1 R 12 3-n1 , -Z 4-SiR a1 k1 R b1 l1 R c1 m1 , -Z 4 -CR d1 k2 R e1 l2 R 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 have the same meanings as above.

[0281] In a preferred embodiment, R g1 and R h1 are each independently -Z 4 -SiR 11 n1 R 12 3-n1 is.

[0282] Above Z 4 are each independently a single bond, an oxygen atom, or a divalent organic group. 4 The structure written as 11 n1 R 12 3-n1 )

[0283] In one embodiment, Z 4 is an oxygen atom.

[0284] In one embodiment, Z 4 is a divalent organic group.

[0285] In a preferred embodiment, Z 4 does not contain siloxane bonds.

[0286] Above Z 4 is preferably C 1-30Alkylene group, -(CH2) z5” -O-(CH2) z6” - (wherein z5" is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6, and z6" is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6), or -(CH2) z7” -phenylene-(CH2) z8” - (wherein z7" is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6, and z8" is an integer of 0 to 30, for example, an integer of 1 to 20, an integer of 0 to 6, or an integer of 1 to 6). 1-30 The alkylene group may be straight-chain or branched, but is preferably straight-chain. These groups may contain, for example, fluorine atoms, C 1-30 Alkyl group, C 2-30 Alkenyl groups, and C 2-30 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.

[0287] In a preferred embodiment, Z 4 is C 1-6 Alkylene group or -(CH2) z7” -phenylene-(CH2) z8” -, preferably -phenylene-(CH2) z8” -It is. Z 4 is such a group, the light resistance, particularly the ultraviolet resistance, can be improved.

[0288] In another preferred embodiment, the Z 4 is C 1-3 In one embodiment, Z is an alkylene group. 4 can be -CH2CH2CH2-. In another embodiment, Z 4 can be -CH2CH2-. In another embodiment, Z 4 can be -CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2-.

[0289] In a preferred embodiment, formulas (S1), (S2), (S3), (S4) and (S5) do not contain a siloxane bond.

[0290] In one embodiment, R Si is a group represented by formula (S3), (S4) or (S5).

[0291] In one embodiment, R Si is a group represented by formula (S3) or (S4).

[0292] In one embodiment, R Si is a group represented by formula (S4) or (S5).

[0293] In one embodiment, R Si is a group represented by formula (S1). In a preferred embodiment, formula (S1) is a group represented by formula (S1-b). In a preferred embodiment, in the formula, R 13 is a hydrogen atom, and X 11 is a single bond, or -R 28 -O x -R 29 -(In the formula, R 28 and R 29 are each independently a single bond or C 1-20 It is an alkylene group, and x is 0 or 1.) and n1 is 1 to 3, preferably 2 to 3, and more preferably 3.

[0294] In one embodiment, R Si is a group represented by formula (S2). In a preferred embodiment, formula (S2) is -SiR 11 2nd Round 12 , or -SiR 11 It is 3.

[0295] In one embodiment, R Si is a group represented by formula (S3). In a preferred embodiment, formula (S3) is -SiR a1 2nd Round 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, -(CH2) z1 -O-(CH2) z2 - (wherein z1 is an integer of 0 to 6, for example, an integer of 1 to 6, and z2 is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z3 -phenylene-(CH2) z4 - (wherein z3 is an integer of 0 to 6, for example, an integer of 1 to 6, and z4 is an integer of 0 to 6, for example, an integer of 1 to 6), preferably C 1-6 It is an alkylene group, and q1 is 1 to 3, preferably 2 to 3, and more preferably 3.

[0296] In one embodiment, R Si is a group represented by formula (S4). In a preferred embodiment, formula (S4) is -CR e1 2nd Round 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, -(CH2) z5” -O-(CH2) z6” - (wherein z5" is an integer of 0 to 6, for example, an integer of 1 to 6, and z6" is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z7” -phenylene-(CH2) z8” - (wherein z7" is an integer of 0 to 6, for example, an integer of 1 to 6, and z8" is an integer of 0 to 6, for example, an integer of 1 to 6), preferably C 1-6 It is an alkylene group, and n2 is 1 to 3, preferably 2 to 3, and more preferably 3.

[0297] In one embodiment, R Si is a group represented by formula (S5). In a preferred embodiment, R g1 and Rh1 -Z 4 -SiR 11 n1 R 12 3-n1 and Z 4 is C 1-6 Alkylene group, -(CH2) z5” -O-(CH2) z6” - (wherein z5" is an integer of 0 to 6, for example, an integer of 1 to 6, and z6" is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z7” -phenylene-(CH2) z8” - (wherein z7" is an integer of 0 to 6, for example, an integer of 1 to 6, and z8" is an integer of 0 to 6, for example, an integer of 1 to 6), preferably C 1-6 It is an alkylene group, and n1 is 1 to 3, preferably 2 to 3, and more preferably 3.

[0298] The fluorine-containing silane compound represented by the above formula (1) is not particularly limited, but may be 1×10 2 ~1×10 5 The fluorine-containing silane compound represented by the above formula (1) preferably has a number average molecular weight of 100 to 30,000, more preferably 100 to 10,000, from the viewpoint of friction durability. The "number average molecular weight" is defined as 1 The value is measured by H-NMR.

[0299] Examples of the fluorine-containing silane compound represented by formula (1) include those having the following structure: [ka]

[0300] R 53 is a hydrogen atom or a monovalent organic group. Examples include a hydrogen atom and a methyl group. R Si has the same meaning as above.

[0301] In formula (T1), F3C-R k11 - is Rf1 -C(=O)NR 53 -R k12 - is X A correspond to the following: R k11 is a single bond or C 1-30 Alkylene groups (e.g., C 1-9 alkylene group), for example, a single bond. R k12 is a single bond or C 1-30 Alkylene groups, such as C 1-10 It is an alkylene group.

[0302] In formula (T2), F3C-R k21 - is Rf 1 -C(=O)NR 53 -R k22 - is X A correspond to the following, respectively. R k21 is a single bond or C 10-200 Alkylene groups, such as C 10-30 It is an alkylene group. R k22 is a single bond or C 1-200 Alkylene groups, such as C 1-10 It is an alkylene group.

[0303] In formula (T3), F3C-[(CH2) g1 -SiR s 2O-(SiR s 2O) n11 -SiR s 2]-(CH2) g1 - is Rf 1 -C(=O)NR 53 -R k33 - is X A correspond to the following, respectively. Each g1 is independently an integer of 0 to 30. R k33 is a single bond or C 1-200 Alkylene groups, such as C 1-10 It is an alkylene group. However, the total of the number of carbon atoms and g1 is 0 to 200. R s , n11 has the same meaning as above.

[0304] In formula (T4), F3C-(R k41 ) k411 -(OR k42 ) k412 - is Rf 1 -C(=O)NR 53 -R k43 - is X A correspond to the following, respectively. R k41 and R k42 is a single bond or an alkylene group. k411 is 0 or 1. k412 is an integer between 0 and 150. However, -(R k41 ) k411 -(OR k42 ) k412 The number of carbon atoms included in - is an integer of 1 to 150. R k43 is a single bond or C 1-30 Alkylene groups (e.g., C 1-20 alkylene group), for example, C 1-10 It is an alkylene group. R k41 is a single bond or C 1-30 Alkylene groups (e.g., C 1-20 alkylene group), such as a methylene group or an ethylene group, k is 1, and R k42 is C 1-6 It is an alkylene group, for example, an ethylene group, and k412 is an integer of 1 to 50.

[0305] In formula (T5), F3C-R k51 - is Rf 1 -OC(=O)NR 53 -R k52 - is X A correspond to the following, respectively. R k51 is a single bond or C 1-200 is an alkylene group, e.g., a single bond or C 1-30 It is an alkylene group. R k52 is a single bond or C 1-200 Alkylene groups, such as C 10-30 It is an alkylene group.

[0306] In formula (T6), F3C-R k61 - is Rf 1 This applies to: R k61 is C 1-200 Alkylene groups, such as C 1-30 It is an alkylene group.

[0307] In equation (T7), F3C-R k71 -OR k72 - is Rf 1 This applies to: R k71 and R k72 are each independently a single bond or C 1-200 It is an alkylene group. k71 and R k72 The total number of carbon atoms is an integer of 0 to 200. For example, R k71 and R k72 are each independently a single bond or C 1-30 It is an alkylene group.

[0308] The fluorine-containing silane compound represented by formula (1) is preferably Rf 1 is R A1 -X B - and R A1 is CF3- or CF3O-, X B is a single bond, X A is -(p-phenylene) v1 -(CH2) v2 -R 57 v3 -(CH2) v4 - and R 57 is -CONH-, -NHCO-, -COO-, or -O-, v1 is 0 or 1, v2 is an integer between 0 and 20, v3 is 0 or 1, v4 is an integer from 2 to 20, R Si -SiR 11 3, R 11 is a methoxy group, α1 is 1, α2 is 1, It is a fluorine-containing silane compound.

[0309] Specific examples of the fluorine-containing silane compound represented by formula (1) include those having the following structures: TIFF2026035630000016.tif250158 TIFF2026035630000017.tif254164 TIFF2026035630000018.tif250156 TIFF2026035630000019.tif250146 TIFF2026035630000020.tif99132

[0310] [Manufacturing method] The method for producing the fluorine-containing silane compound of the present disclosure will be described below. However, the method for producing the fluorine-containing silane compound of the present disclosure is not limited to the following method.

[0311] Methods for producing a group containing F3C- (trifluoromethyl group) include a method of deriving it from a compound having F3C-, and a method of introducing it by fluorinating a functional group.

[0312] (Manufacturing method 1) The manufacturing method includes the following steps. Step (I): Compound (11): F3C-R j111 -NH2 was used as a raw material to synthesize the isocyanate compound (12): O=C=NR j112 -R Si to produce a fluorine-containing silane compound (13). [ka]

[0313] R j111 is a single bond, an alkylene group, or an alkylene group containing an ether bond. j111 is, for example, a single bond, C 1-30 Alkylene groups, specifically methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, or eicosadecylene groups, or groups having an O atom at the left end of the above groups. Specific examples of the compound (11) include 2,2,2-trifluoroethylamine and 3,3,3-trifluoropropylamine. R j112 is a single bond or an alkylene group, for example, an alkylene group, specifically C 1-30 It is an alkylene group. Specific examples of the isocyanate compound (12) include 3-(trimethoxysilyl)propyl isocyanate. R Si has the same meaning as above. For example, R Si is expressed by equation (S2).

[0314] The reaction can be carried out in a solvent. The solvent is preferably one that can dissolve Compounds (11) to (13). The solvents can be used alone or in combination of two or more.

[0315] The solvent is, for example, a non-fluorinated solvent or a fluorinated solvent.

[0316] Examples of non-fluorine-based solvents include S atom-containing solvents, amide-based solvents, ester-based solvents, ketone-based solvents, ether-based solvents, halogen-containing solvents, and hydrocarbon-based solvents.

[0317] Examples of the S atom-containing solvent include dimethyl sulfoxide, sulfolane, dimethyl sulfide, and carbon disulfide. Examples of the amide solvent include N-methylpyrrolidone, N,N-dimethylformamide, dimethylacetamide, and hexamethylphosphoric triamide. Examples of ester solvents include methyl acetate, ethyl acetate, propyl acetate, n-butyl acetate, isopropyl acetate, isobutyl acetate, cellosolve acetate, propylene glycol methyl ether acetate, carbitol acetate, diethyl oxalate, ethyl pyruvate, ethyl 2-hydroxybutyrate, ethyl acetoacetate, amyl acetate, methyl lactate, ethyl lactate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 2-hydroxyisobutyrate, and ethyl 2-hydroxyisobutyrate. Examples of the ketone solvent include acetone, methyl ethyl ketone, methyl isobutyl ketone, 2-hexanone, cyclohexanone, methyl amino ketone, and 2-heptanone. Examples of the ether solvent include diethyl ether, tetrahydrofuran, cyclopentyl methyl ether, ethylene glycol, monoglyme, and diglyme. Examples of the halogen-containing solvent include dichloromethane and chloroform. Examples of hydrocarbon solvents include pentane, hexane, heptane, benzene, and toluene.

[0318] A fluorine-based solvent is a solvent containing one or more fluorine atoms. Examples of fluorine-based solvents include compounds in which at least one hydrogen atom of a hydrocarbon is substituted with a fluorine atom, such as hydrofluorocarbons, hydrochlorofluorocarbons, and perfluorocarbons; hydrofluoroethers, etc. Here, the term "hydrocarbon" refers to a compound containing only carbon atoms and hydrogen atoms.

[0319] Examples of hydrofluorocarbons include bis(trifluoromethyl)benzene, specifically 1,3-bis(trifluoromethyl)benzene (m-XHF), 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorooctane, and CF 13 Examples include CH2CH3 (for example, Asahiklin (registered trademark) AC-6000 manufactured by Asahi Glass Co., Ltd.), 1,1,2,2,3,3,4-heptafluorocyclopentane (for example, Zeorora (registered trademark) H manufactured by Zeon Corporation).

[0320] Examples of hydrochlorofluorocarbons include HCFC-225 (for example, Asahiklin AK-225 manufactured by AGC Corporation) and HFO-1233zd(Z) (for example, Cerefin 1233Z manufactured by Central Glass Co., Ltd.).

[0321] Examples of perfluorocarbons include perfluorohexane, perfluoromethylcyclohexane, perfluoro-1,3-dimethylcyclohexane, and perfluorobenzene.

[0322] Examples of hydrofluoroethers include alkyl perfluoroalkyl ethers (the perfluoroalkyl group and alkyl group may be linear or branched) such as perfluoropropyl methyl ether (C3F7OCH3) (e.g., Novec™ 7000 manufactured by Sumitomo 3M Limited), perfluorobutyl methyl ether (C4F9OCH3) (e.g., Novec™ 7100 manufactured by Sumitomo 3M Limited), perfluorobutyl ethyl ether (C4F9OC2H5) (e.g., Novec™ 7200 manufactured by Sumitomo 3M Limited), and perfluorohexyl methyl ether (C2F5CF(OCH3)C3F7) (e.g., Novec™ 7300 manufactured by Sumitomo 3M Limited); CF3CH2OCF2CHF2 (e.g., Asahiklin™ AE-3000 manufactured by Asahi Glass Co., Ltd.); and the like.

[0323] Of the fluorine-based solvents listed above, m-XHF, HFE7100, HFE7200, HFE7300, AC-6000, perfluorohexane, and perfluorobenzene are preferred.

[0324] The solvent is preferably at least one selected from the group consisting of diethyl ether, tetrahydrofuran, cyclopentyl methyl ether, ethylene glycol, dichloromethane, chloroform, benzene, toluene, and 1,3-bis(trifluoromethyl)benzene, and more preferably at least one selected from the group consisting of dichloromethane, chloroform, toluene, and 1,3-bis(trifluoromethyl)benzene.

[0325] The reaction temperature is not particularly limited, and may be, for example, 0 to 100°C, 0 to 50°C, or 0 to 30°C.

[0326] (Manufacturing method 2) In this production method, an olefin-containing amide compound is produced by reacting an olefin (-CH=CH2)-containing amine compound with a carbonyl group (-C(=O)-)-containing compound having CF3 at the terminal, and the fluorine-containing silane compound of the present disclosure can be synthesized from this olefin-containing amide compound. For example, a fluorine-containing silane compound of the present disclosure can be synthesized by reacting an amide compound having an olefin at the terminal with a compound of 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 fluorine-containing 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.

[0327] The olefin-containing amine compound is a compound having H2N- and -CH=CH2, for example, H2N(CH2) x31 Q((CH2) x32 CH=CH2) x33 R x3 x34 (In the formula, x31 is an integer of 0 to 30, x32 is an integer of 0 to 6, x33 is an integer of 1 or more, x34 is an integer of 0 or more, the sum of x33 and x34 is the valence of Q minus 1, Q is N, Si, C, R x3 is a hydrogen atom, a hydroxyl group, or a monovalent organic group). Examples of olefin-containing amine compounds include allylamine, diallylamine, 2-allylpent-4-en-1-amine (HNCHCH(CHCH=CH)), 2,2-diallylpent-4-en-1-amine (HN—CHC(CHCH=CH)), 3-buten-1-amine, 4-penten-1-amine, 5-hexen-1-amine, 6-hepten-1-amine, 7-octen-1-amine, 8-nonen-1-amine, and 9-decen-1-amine. , 10-undecene-1-amine, 11-dodecene-1-amine, 12-tridecen-1-amine, 13-tetradecene-1-amine, 14-pentadecen-1-amine, 15-hexadecen-1-amine, 16-heptadecen-1-amine, 17-octadecene-1-amine, 18-nonadecen-1-amine, 19-icosene-1-amine, 20-henicosene-1-amine, 23-tetracosene-1-amine, 29-triaconten-1-amine, and the like.

[0328] The carbonyl group-containing compound is a compound containing an FC- group and a C(=O) group. The carbonyl group-containing compound may be a compound obtained by the synthesis method described below, or a compound represented by the formula (21): [ka] Examples of the compound include compounds represented by the following formula:

[0329] In equation (21), R j13 is a single bond, an alkylene group, or an alkylene group containing an ether bond, for example a single bond; Rj14 is a hydroxyl group, a fluorine atom, a chlorine atom, or an —O-lower alkyl group (that is, an alkoxide group), for example, a hydrogen atom, a methoxide group, or an ethoxide group, specifically a hydrogen atom or a methoxide group. Specific examples of the compound of formula (21) include compounds having a terminal carboxyl group, such as trifluoroacetic acid, 3,3,3-trifluoropropionic acid, 4,4,4-trifluorobutyric acid, 5,5,5-trifluorovaleric acid, 6,6,6-trifluorocaproic acid, 7,7,7-trifluoroheptanoic acid, 8,8,8-trifluorooctanoic acid, 9,9,9-trifluorononanoic acid, 10,10,10-trifluorodecanoic acid, 12,12,12-trifluorolauric acid, 14,14,14-trifluoromyristic acid, 16,16,16-trifluoro-palmitic acid, 17,17,17-trifluoro-margaric acid, and 18,18,18-trifluorostearic acid, as well as the corresponding methyl esters, corresponding ethyl esters, and acid chlorides.

[0330] When the carbonyl group-containing compound has an acid chloride (C(=O)Cl), an olefin-containing amide compound can be obtained by reacting it with an olefin-containing amine compound in the presence of a trialkylamine, such as triethylamine.

[0331] When the carbonyl group-containing compound has a carboxylic acid, an olefin-containing amide compound can be obtained by reacting it with a condensing agent. Condensing agents include 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDC), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC·HCl), N,N'-dicyclohexylcarbodiimide (DCC), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), and 1-[bis(dimethylamino)methylene]-1H-benzotriazolium 3-oxide hexafluorophosphate (HBTU), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide tetrafluoroborate (TATU), 1-[bis(dimethylamino)methylene]-1H-benzotriazolium 3-oxide tetrafluoroborate (TBTU), (1-cyano-2-ethoxy-2-oxoethylideneaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate (COM U), O-[(ethoxycarbonyl)cyanomethyleneamino]-N,N,N',N'-tetramethyluronium hexafluorophosphate (HOTU), 1H-benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBOP), 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP), bromotripyrrolidinophosphonium hexafluorophosphate (PyBroP), di Phenylphosphoryl azide (DPPA), 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM), 1-hydroxybenzotriazole (HOBt), 1-hydroxy-7-azabenzotriazole (HOAt) are preferred, and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, N,N'-dicyclohexylcarbodiimide, and 1-hydroxybenzotriazole are preferred. Furthermore, 4-dimethylaminopyridine (DMAP) or the like may be added as a catalyst.

[0332] When the carbonyl group-containing compound has an ester, an olefin-containing amide compound can be obtained by reacting it in the presence of a base. As the base, 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), 1,2,4-triazole, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), sodium methoxide, or sodium tert-butoxide is preferably used, and 1,5,7-triazabicyclo[4.4.0]dec-5-ene is more preferably used.

[0333] The reaction temperature is not particularly limited, and may be, for example, 0 to 150°C, 0 to 100°C, or 0 to 50°C. The solvent can be the same as that used in Production Method 1. Preferred are acetonitrile, dichloromethane, chloroform, toluene, diethyl ether, and tetrahydrofuran. The reaction may also be carried out without a solvent.

[0334] (Manufacturing method 3) In this production method, an olefin group-containing compound is used as a raw material to produce a fluorine-containing silane compound. The olefin group-containing compound is a compound having F3C- and an olefin group (-CH=CH2). Examples of the olefin group-containing compound include compounds obtained by the synthesis method described below. Examples of the olefin group-containing compound include 3,3,3-trifluoropropene, 4,4,4-trifluoro-1-butene, 5,5,5-trifluoro-1-pentene, 6,6,6-trifluoro-1-hexene, 7,7,7-trifluoro-1-heptene, 8,8,8-trifluoro-1-octene, 9,9,9-trifluoro-1-nonene, 10,10,10-trifluoro-1-decene, 11,11,11-trifluoro-1-undecene, 12,12,12-trifluoro-1-dodecene, 13,13,13-trifluoro-1-tridecene, 14,1 Examples include 4,14-trifluoro-1-tetradecene, 15,15,15-trifluoro-1-pentadecene, 16,16,16-trifluoro-1-hexadecene, 17,17,17-trifluoro-1-heptadecene, 18,18,18-trifluoro-1-octadecene, 19,19,19-trifluoro-1-nonadecene, 20,20,20-trifluoro-1-icosene, 21,21,21-trifluoro-1-henicosene, 24,24,24-trifluoro-1-tetracosene, and 30,30,30-trifluoro-1-triacontene.

[0335] For example, the olefin group may be HSiM3 (where each M is independently a halogen atom or C 1-6 alkoxy group), and then the resulting compound is Formula: Hal-J-CH=CH2 (wherein J represents Mg, Cu, Pd or Zn, and Hal represents a halogen atom.) and optionally a compound represented by Formula:R c h’ L (wherein, R c is the same as above, and L is R c represents a group capable of bonding to, and h' is an integer of 1 to 3. to produce the following compound: [ka] (-R j21 -CH2CH2- is X B For example, -R j21-CH2CH2- is an alkylene group or an alkylene group containing an ether bond, such as C 1-30 C containing alkylene group or ether bond 1-30 Alkylene groups, specifically C 10-25 C containing alkylene group or ether bond 10-25 an alkylene group; and The compound is prepared by reacting HSiM3 (wherein each M is independently a halogen atom or C 1-6 an alkoxy group), and optionally Formula:R 23 i’ L'(where R 23 is as defined above, and L' is R 23 represents a group capable of bonding to, and i' is an integer of 1 to 3. and optionally a compound represented by Formula:R 24 j’ L” (in the formula, R 24 is the same as above, and L" is R 24 represents a group capable of bonding to, and j' is an integer of 1 to 3. reacting a compound represented by by a method comprising the steps of: F3C-R j22 -R Si (R j22 is a divalent organic group, -R j21 Corresponds to -CH2CH2-. R Si has the same meaning as above.) The above description can also be applied to other olefin group-containing compounds.

[0336] (Manufacturing method 4) In this production method, a fluorine-containing silane compound is produced by reacting a carbonyl group-containing compound with an amine-containing silane compound.

[0337] The carbonyl group-containing compound is a compound containing F3C- and C(=O). The carbonyl group-containing compound includes a compound obtained by the synthesis method described below, or a compound represented by the formula (21): [ka] Examples of compounds represented by R j13 and R j14 has the same meaning as above.

[0338] Amine-containing silane compounds are formed by combining H2N- groups with R Si The amine-containing silane compound is, for example, a compound having a HN-R group. j23 -R Si Specifically, aminopropyltrimethoxysilane can be mentioned. j23 is an alkylene group, e.g., C 1-4 alkylene groups, specifically methylene groups, ethylene groups, and propylene groups; Si has the same meaning as above, for example, R Si is expressed by equation (S2).

[0339] The fluorine-containing silane compound is, for example, F3C-R j24 -C(=O)NHR j23 -R Si The above F3C-R j24 -Rf 1 - applies. R j24 is an alkylene group, e.g., C 1-4 It is an alkylene group, specifically a methylene group, an ethylene group, a propylene group, or any of the above groups having O at the left end.

[0340] The reaction temperature is preferably 0°C to 150°C, more preferably 20°C to 100°C. The solvent used can be the same as in Production Method 1, and preferably toluene, dichloromethane, chloroform, methanol, or ethanol.

[0341] (Manufacturing method 5) In this production method, a fluorine-containing silane compound is produced by reacting an olefin group-containing compound. Specifically, the olefin group-containing compound may be a compound having the following formula: HSiR j25 m3 R j26 3-m3 [In the formula, R j25 are each independently a hydroxyl group or a hydrolyzable group, R j26 are each independently a monovalent organic group, m3 is 1 to 3. A fluorine-containing silane compound can be obtained by reacting a compound represented by the formula: The above description can also be applied to other olefin group-containing compounds.

[0342] The olefin group-containing compound is a compound having F3C- and an olefin group. Examples of the olefin group-containing compound include compounds obtained by the synthesis method described below.

[0343] The reaction temperature is preferably from -20°C to 150°C, more preferably from 0°C to 100°C. The solvent may be the same as that used in Production Method 1, and preferably toluene, dichloromethane, chloroform, methanol, ethanol, diethyl ether, or cyclopentyl methyl ether.

[0344] (Synthesis method 1) In this method, a compound (31): F3C-R j33 Using -OH as a raw material, a carbonyl group-containing compound is synthesized. R j33 is an alkylene group or an alkylene group containing an ether bond, for example, C 1-30 C containing alkylene group or ether bond 1-30 It is an alkylene group. Specific examples of the compound (31) include trifluoroethanol, trifluoropropanol, and trifluorobutanol.

[0345] The hydroxyl group of compound (31) is converted to -OTf (Tf is a trifluoromethylsulfonyl group) by a conventional method to give compound (32): F3C-R j33 -OTf is obtained.

[0346] The method comprises the following step (I'): (I'): The compound (32) is mixed with a compound (33) having a reactive group to obtain a carbonyl group-containing compound (34). [ka]

[0347] Here, examples of the reactive group include a hydroxyl group, a carboxyl group, Cl, F, and an ester group obtained by esterifying a carboxyl group. Specific examples of the compound (33) having a reactive group include tert-butyl 9-hydroxy-4,7-dioxanonanoate, tert-butyl 12-hydroxy-4,7,10-trioxadodecanoate, tert-butyl 1-hydroxy-3,6,9,12-tetraoxapentadecano-15-oate, Examples of the hydroxyl group include compounds having a terminal hydroxyl group such as tert-butyl; and compounds having a terminal carboxyl group such as 10-hydroxydecanoic acid, 11-hydroxyundecanoic acid, 12-hydroxydodecanoic acid, 13-hydroxytridecanoic acid, 14-hydroxytetradecanoic acid, 15-hydroxypentadecanoic acid, 16-hydroxyhexadecanoic acid, 17-hydroxyheptadecanoic acid, 18-hydroxyoctadecanoic acid, 19-hydroxynonadecanoic acid, 20-hydroxyeicosanoic acid, 21-hydroxyheneicosanoic acid, 22-hydroxydocosanoic acid, 23-hydroxytricosanoic acid, 24-hydroxytetracosanoic acid, 25-hydroxypentacosanoic acid, and 30-hydroxytriacontanoic acid, as well as methyl esters and acid chlorides thereof.

[0348] R j31 is a divalent organic group, for example, a group having a polyether group or an alkylene group, specifically, -(R j35 O) n -R j36-group or C 1-30 It is an alkylene group. Above R j35 is C 1-3 Alkylene groups, such as ethylene groups, j36 is C 1-3 An alkylene group, for example an ethylene group. The above n is an integer of 2 to 150, for example, an integer of 2 to 50. R j32 is a lower alkyl group, for example, a methyl group, an ethyl group, a propyl group, a butyl group, or a tert-butyl group, and specifically a methyl group or a tert-butyl group.

[0349] The reaction temperature is not particularly limited, and can be, for example, -80 to 200°C, e.g., -50 to 100°C, specifically -20 to 50°C. The solvent used can be the same as that used in Production Method 1.

[0350] (Synthesis method 2) In this method, a compound (31): F3C-R j33 An olefin-containing compound is synthesized using —OH as a raw material. Each symbol has the same meaning as above.

[0351] The hydroxyl group of compound (31) is converted to -OTf (Tf is a trifluoromethylsulfonyl group) by a conventional method to obtain compound (32): F3C-R j33 - Manufacture OTf.

[0352] The method comprises the following step (I'): (I'): Compound (32) and compound (35) having a reactive group: HO-R j31 -CH=CH2 to give the olefin-containing compound (36). [ka]

[0353] R j33 and R j31 has the same meaning as above. The reaction temperature and solvent are the same as in Production Method 2.

[0354] (Synthesis method 3) In this method, methyl halodifluoroacetate and compound (41) having a terminal halogen atom: X—(CH n -R j41 (In the formula, R j41 are CH=CH2, COOH, COOR j42 , or COR j43 , R j42 is C 1-6 is an alkyl group, and R j43 is a halogen atom, preferably a chlorine atom, X is a halogen atom, preferably a bromine atom, and n is any integer.) is reacted with a copper salt such as copper iodide in the presence of a fluoride ion such as potassium fluoride to give CF3-(CH2) n -R j41 The halodifluoromethyl acetates include methyl chlorodifluoroacetate, methyl bromodifluoroacetate, and methyl difluoroiodoacetate. By using an olefin compound (41) having a halogen atom at the terminal, R j41 A compound in which the formula is CH=CH2 can be obtained. Specific examples of the olefin compound (41) having a halogen atom at the terminal include allyl chloride, allyl bromide, and allyl iodide.

[0355] (Synthesis method 4) In this method, methyl difluoro(fluorosulfonyl)acetate and an olefin compound (41) having a halogen atom at the terminal: X-(CH2) n -R j41 (In the formula, R j41 are CH=CH2, COOH, COOR j42 , or COR j43 , R j42 is C 1-6 is an alkyl group, and R j43 is a halogen atom, preferably a chlorine atom, X is a halogen atom, preferably a bromine atom, and n is an integer.) in the presence of a copper salt such as copper iodide to give CF3-(CH2)n -R j41 By using an olefin compound (41) having a halogen atom at the terminal, R j41 A compound in which the formula is CH=CH2 can be obtained. Specific examples of the olefin compound (41) having a halogen atom at the terminal include allyl chloride, allyl bromide, and allyl iodide.

[0356] (Synthesis method 5) In this method, (trifluoromethyl)trimethylsilane and an aldehyde having a functional group at the end are reacted in the presence of fluoride ions such as tetrabutylammonium fluoride to form CF3-CH(OH)(CH2). n -R j41 (In the formula, R j41 are CH=CH2, COOH, COOR j42 , or COR j43 , R j42 is C 1-6 is an alkyl group, and R j43 is a halogen atom, preferably a chlorine atom, X is a halogen atom, preferably a bromine atom, and n is an arbitrary integer.) is synthesized, and the hydroxyl group is oxidized to obtain CF3-C(=O)(CH2) n -R j41 By using an aldehyde having an olefin at the terminal, R j41 A compound in which CH=CH2 is obtained. Specific examples of aldehydes having a terminal olefin include 2-propenal, 3-butenal, 4-pentenal, 5-hexenal, 6-heptenal, 7-octenal, 8-nonenal, 9-decenal, 10-undecenal, 11-dodecenal, 12-tridecenal, 13-tetradecenal, 14-pentadecenal, 15-hexadecenal, 16-heptadecenal, 17-octadecenal, 18-nonadecenal, 19-icosenal, 20-henicosenal, 23-tetracosenal, and 29-tridecenal. Examples of oxidizing agents for hydroxyl groups include 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one.

[0357] (Synthesis method 6) In this method, carboxylic acids or esters having a halogen at the end are reacted with thiophosgene in the presence of fluoride ions such as potassium fluoride to produce CF3-S-(CH2) n -C(=O)OR j51 (wherein R j51 is a hydrogen atom or C 1-4 The ester having a halogen atom at the terminal is specifically methyl 10-bromodecanoate, methyl 11-bromoundecanoate, methyl 12-bromododecanoate, methyl 13-bromotridecanoate, methyl 14-bromotetradecanoate, methyl 15-bromopentadecanoate, methyl 16-bromohexadecanoate, methyl 17-bromoheptadecanoate, methyl 18-bromooctadecanoate, methyl 19-bromononadecanoate, methyl 20-bromoeicosanoate, methyl 21-bromoheneicosanoate, methyl 22-bromodocosanoate, methyl 23-bromotricosanoate, methyl 24-bromotetracosanoate, methyl 25-bromopentacosanoate, methyl 30-bromotriacosanoate, methyl 31-bromotriacosanoate, methyl 32-bromotriacosanoate, methyl 33-bromotriacosanoate, methyl 34-bromotriacosanoate, methyl 35-bromotriacosanoate, methyl 36-bromotriacosanoate, methyl 37-bromotriacosanoate, methyl 38-bromotriacosanoate, methyl 39-bromotriacosanoate, methyl 40-bromotriacosanoate, methyl 41-bromoheneicosanoate, methyl 42-bromodocosanoate, methyl 43-bromotricosanoate, methyl 44-bromotetracosanoate, methyl 25-bromopentacosanoate, methyl 46-bromotriacosanoate, methyl 47-bromotriacosanoate, methyl 48-bromotriacosanoate, methyl 49-bromotriacosanoate, Examples of suitable bromoisopropyl ethers include methyl tanoate, ethyl 10-bromodecanoate, ethyl 11-bromoundecanoate, ethyl 12-bromododecanoate, ethyl 13-bromotridecanoate, ethyl 14-bromotetradecanoate, ethyl 15-bromopentadecanoate, ethyl 16-bromohexadecanoate, ethyl 17-bromoheptadecanoate, ethyl 18-bromooctadecanoate, ethyl 19-bromononadecanoate, ethyl 20-bromoeicosanoate, ethyl 21-bromoheneicosanoate, ethyl 22-bromodocosanoate, ethyl 23-bromotricosanoate, ethyl 24-bromotetracosanoate, ethyl 25-bromopentacosanoate, and ethyl 30-bromotriacontanoate.

[0358] (Synthesis method 7) In this method, olefins having a halogen at the end are reacted with thiophosgene in the presence of fluoride ions such as potassium fluoride to produce CF3-S-(CH2) n-CH=CH2 is synthesized. Specific examples of olefins having a halogen at the terminal include 11-bromoundecene, 12-bromododecene, 13-bromotridecene, 14-bromotetradecene, 15-bromopentadecene, 16-hexadecene, 17-heptadecene, 18-bromooctadecene, 19-bromononadecene, 20-bromoicosene, 21-bromohenicosene, 24-bromotetracosene, and 30-bromotriacontene.

[0359] (Synthesis method 8) In this method, for a carboxylic acid or ester containing a halogen, [(CH3)4N] + By reacting [N(CF3)2], (CF3)2N-(CH2) n -C(=O)OR j51 (wherein R j51 is a hydrogen atom or C 1-4The ester having a halogen atom at the terminal is specifically methyl 10-bromodecanoate, methyl 11-bromoundecanoate, methyl 12-bromododecanoate, methyl 13-bromotridecanoate, methyl 14-bromotetradecanoate, methyl 15-bromopentadecanoate, methyl 16-bromohexadecanoate, methyl 17-bromoheptadecanoate, methyl 18-bromooctadecanoate, methyl 19-bromononadecanoate, methyl 20-bromoeicosanoate, methyl 21-bromoheneicosanoate, methyl 22-bromodocosanoate, methyl 23-bromotricosanoate, methyl 24-bromotetracosanoate, methyl 25-bromopentacosanoate, methyl 30-bromotriacosanoate, methyl 31-bromotriacosanoate, methyl 32-bromotriacosanoate, methyl 33-bromotriacosanoate, methyl 34-bromotriacosanoate, methyl 35-bromotriacosanoate, methyl 36-bromotriacosanoate, methyl 37-bromotriacosanoate, methyl 38-bromotriacosanoate, methyl 39-bromotriacosanoate, methyl 40-bromotriacosanoate, methyl 41-bromoheneicosanoate, methyl 42-bromodocosanoate, methyl 43-bromotricosanoate, methyl 44-bromotetracosanoate, methyl 25-bromopentacosanoate, methyl 46-bromotriacosanoate, methyl 47-bromotriacosanoate, methyl 48-bromotriacosanoate, methyl 49-bromotriacosanoate, Examples of suitable bromoisopropyl ethers include methyl tanoate, ethyl 10-bromodecanoate, ethyl 11-bromoundecanoate, ethyl 12-bromododecanoate, ethyl 13-bromotridecanoate, ethyl 14-bromotetradecanoate, ethyl 15-bromopentadecanoate, ethyl 16-bromohexadecanoate, ethyl 17-bromoheptadecanoate, ethyl 18-bromooctadecanoate, ethyl 19-bromononadecanoate, ethyl 20-bromoeicosanoate, ethyl 21-bromoheneicosanoate, ethyl 22-bromodocosanoate, ethyl 23-bromotricosanoate, ethyl 24-bromotetracosanoate, ethyl 25-bromopentacosanoate, and ethyl 30-bromotriacontanoate.

[0360] (Synthesis method 9) This method uses [(CH3)4N] for olefins with terminal halogens. + By reacting [N(CF3)2], (CF3)2N-(CH2) n -CH=CH2 is synthesized. Specific examples of olefins having a halogen at the terminal include 11-bromoundecene, 12-bromododecene, 13-bromotridecene, 14-bromotetradecene, 15-bromopentadecene, 16-hexadecene, 17-heptadecene, 18-bromooctadecene, 19-bromononadecene, 20-bromoicosene, 21-bromohenicosene, 24-bromotetracosene, and 30-bromotriacontene.

[0361] (Synthesis method 10) In this method, a compound (101) having a hydroxyl group and a carbonyl group: HO-R j33 -COOR j32 is used as a raw material to synthesize a trifluoromethoxy group-containing compound. R j33 is an alkylene group, e.g., C 1-30 It is an alkylene group. Specific examples of compound (101) include compounds having a terminal carboxyl group, such as 3-hydroxypropionic acid, 4-hydroxybutyric acid, 5-hydroxyvaleric acid, 6-hydroxyhexanoic acid, 7-hydroxyheptanoic acid, 8-hydroxyoctanoic acid, 9-hydroxynonanoic acid, 10-hydroxydecanoic acid, 12-hydroxylauric acid, 14-hydroxymyristic acid, 16-hydroxypalmitic acid, 17-hydroxyheptadecanoic acid, 18-hydroxystearic acid, 20-hydroxyeicosanoic acid, 21-hydroxyheneicosanoic acid, 22-hydroxydocosanoic acid, 23-hydroxytricosanoic acid, 24-hydroxytetracosanoic acid, 25-hydroxypentacosanoic acid, and 30-hydroxytriacontanoic acid, as well as methyl esters and acid chlorides thereof.

[0362] The hydroxyl group of compound (101) is reacted with carbon disulfide in the presence of a base such as sodium hydride, and iodomethane is added to give xanthate ester (102): HCS-C(=S)-OR. j33 -COOR j32 The xanthate ester (102) is reacted with hydrogen fluoride pyridine and 1,3-dibromo-5,5-dimethylhydantoin to obtain the desired trifluoromethoxy group-containing compound (103): FCO-R j33 -COOR j32 get.

[0363] Alternatively, the hydroxyl group of compound (101) can be reacted with arylsulfonic acid trifluoromethyl ester in the presence of cesium fluoride, tetrabutylammonium bromide, or the like in an aprotic polar solvent such as NMP, DMF, or HMPA (hexamethylphosphoric triamide) to give the desired trifluoromethoxy group-containing compound (103): FCO-R j33 -COOR j32 get.

[0364] (Synthesis method 11) In this method, a compound (111) having a hydroxyl group and an olefin: HO-R j33 Using -CH=CH2 as a raw material, a trifluoromethoxy group-containing compound is synthesized. R j33 is an alkylene group, e.g., C 1-30 It is an alkylene group. Examples of olefin group-containing compounds include 3-hydroxypropene, 4-hydroxy-1-butene, 5-hydroxy-1-pentene, 6-hydroxy-1-hexene, 7-hydroxy-1-heptene, 8-hydroxy-1-octene, 9-hydroxy-1-nonene, 10-hydroxy-1-decene, 11-hydroxy-1-undecene, 12-hydroxy-1-dodecene, 13-hydroxy-1-tridecene, 14-hydroxy-1-tetradecene, 15-hydroxy-1-pentadecene, 16-hydroxy-1-hexadecene, 17-hydroxy-1-heptadecene, 18-hydroxy-1-octadecene, 19-hydroxy-1-nonadecene, 20-hydroxy-1-icosene, 21-hydroxy-1-heneicosene, 24-hydroxy-1-tetracosene, and 30-hydroxy-1-triacontene.

[0365] The hydroxyl group of compound (111) was reacted with carbon disulfide in the presence of a base such as sodium hydride, and iodomethane was added to give xanthate ester (112): HCS-C(=S)-OR. j33 -COOR j32The xanthate ester (102) is reacted with hydrogen fluoride pyridine and 1,3-dibromo-5,5-dimethylhydantoin to give the desired trifluoromethoxy group-containing compound (113): FCO-R j33 Obtain -CH=CH2.

[0366] Alternatively, the hydroxyl group of compound (111) can be reacted with arylsulfonic acid trifluoromethyl ester in an aprotic polar solvent such as NMP, DMF, or HMPA (hexamethylphosphoric triamide) in the presence of cesium fluoride, tetrabutylammonium bromide, or the like to give the desired trifluoromethoxy group-containing compound (113): FCO-R j33 Obtain -CH=CH2.

[0367] [Surface treatment agent] The surface treatment agent of the present disclosure will be described below.

[0368] The surface treatment agent of the present disclosure contains at least one fluorine-containing silane compound represented by formula (1).

[0369] The surface treatment agent of the present disclosure may further contain a condensate of a fluorine-containing silane compound.

[0370] In one embodiment, the surface treatment agent of the present disclosure contains at least one of a fluorine-containing silane compound and a compound formed by condensation of at least a portion of the fluorine-containing silane compound.

[0371] 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%, even more preferably 5.0 to 25.0 mass%, and particularly preferably 10.0 to 20.0 mass%, based on the total mass of the surface treatment agent.

[0372] 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.

[0373] 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.

[0374] 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).

[0375] The composition of the present disclosure may contain a solvent, a (non-reactive) silicone compound that can 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, etc.

[0376] 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 The alkylene group may be substituted with one or more substituents, such as a hydroxyl group, -OR 91 (where R 91 is C 1-10 Alkyl groups, preferably C 1-3 alkyl groups, such as methyl groups.

[0377] In one embodiment, the surface treatment agent of the present disclosure is R 81 OR 82 , R 83 n8 C6H6-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:

[0378] The monovalent organic group having 1 to 10 carbon atoms may be linear or branched, and may further contain a cyclic structure.

[0379] 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.

[0380] In another embodiment, the monovalent organic group having 1 to 10 carbon atoms does not contain a halogen atom.

[0381] 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, preferably a hydrocarbon group which is not substituted with a halogen.

[0382] In one embodiment, the hydrocarbon group is linear.

[0383] In another embodiment, the hydrocarbon group is branched.

[0384] In another embodiment, the hydrocarbon group comprises a cyclic structure.

[0385] In one embodiment, the solvent is R 81 OR 82 is.

[0386] R 81 and R 82 are each independently preferably a hydrocarbon group having 1 to 8 carbon atoms, more preferably C 1-6 alkyl groups of C 5-8 It can be a cycloalkyl group of the formula:

[0387] In one embodiment, the solvent is R 83 n8 C6H 6-n8 is.

[0388] C6H 6-n8 is an n8-valent benzene ring. That is, R 83 n8 C6H 6-n8 is n8 R 83 is benzene substituted with

[0389] R 83 are each independently a halogen or a C optionally substituted by a halogen. 1-6 The alkyl group may be:

[0390] n8 is preferably an integer of 1 to 3.

[0391] In one embodiment, the solvent is R 84 R 85 R 86 Si-(O-SiR 87 R 88 ) m8 -R 89 is.

[0392] In one embodiment, the solvent is (OSiR 87 R 88 ) m9 (OSiR 87 R 88 ) m9 is multiple OSiR 87 R 88It is a cyclic siloxane formed by bonding units in a ring.

[0393] R 84 ~R 89 are each independently a hydrogen atom or C 1-6 alkyl groups, preferably C 1-6 alkyl groups of the formula C 1-3 The alkyl group is preferably a methyl group.

[0394] m8 is preferably an integer of 1 to 6, more preferably an integer of 1 to 5, and even more preferably 1 to 2.

[0395] m9 is preferably an integer of 3 to 6, and more preferably an integer of 3 to 5.

[0396] 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; or an alkyl ester 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, 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 cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether, propylene 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, 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; and diethylene glycol monoethyl ether acetate.Polyfluoroaromatic hydrocarbons (e.g., 1,3-bis(trifluoromethyl)benzene); polyfluoroaliphatic hydrocarbons (e.g., CF; 13 CH2CH3 (e.g., Asahiklin (registered trademark) AC-6000 manufactured by Asahi Glass Co., Ltd.), CF 13H (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; CF3CH2OH, CF3 Fluorine-containing alcohols such as CF2CH2OH and (CF3)2CHOH; hydrofluoroethers (HFE) (for example, perfluoropropyl methyl ether (C3F7OCH3) (for example, Novec (trademark) 7000 manufactured by Sumitomo 3M Limited), perfluorobutyl methyl ether (C4F9OCH3) (for example, Novec (trademark) 7100 manufactured by Sumitomo 3M Limited), perfluorobutyl ethyl ether (C4F9OC2H5) (for example, Novec (trademark) 7200 manufactured by Sumitomo 3M Limited), perfluoro alkyl perfluoroalkyl ethers (the perfluoroalkyl group and the alkyl group may be linear or branched) such as fluorohexyl methyl ether (C2F5CF(OCH3)C3F7) (e.g., Novec (trademark) 7300 manufactured by Sumitomo 3M Limited), or CF3CH2OCF2CHF2 (e.g., Asahiklin (registered trademark) AE-3000 manufactured by Asahi Glass Co., Ltd.), hydrofluoroolefins; CF3CH=CHCl (e.g., CELEFIN (registered trademark) 1233Z manufactured by Central Glass Co., Ltd.), ethers such as CHFCF=CHCl (for example, AMOLEA® AS-300 manufactured by Asahi Glass Co., Ltd.) and cyclopentyl methyl ether; siloxanes such as hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, octamethylcyclotetrasiloxane, octamethylcyclopentasiloxane, decamethylcyclopentasiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, and tetradecamethylhexasiloxane; dimethyl sulfoxide; and mixed solvents of two or more of these.Among these, aliphatic hydrocarbons, aromatic hydrocarbons, esters, glycol ethers, alcohols, ether alcohols, and siloxanes are preferred. For example, hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, mineral spirits, benzene, toluene, xylene, naphthalene, methyl acetate, ethyl acetate, propyl acetate, n-butyl acetate, isopropyl acetate, isobutyl acetate, cellosolve acetate, propylene glycol methyl ether acetate, carbitol acetate, diethyl oxalate, ethyl pyruvate, ethyl 2-hydroxybutyrate, ethyl acetoacetate, amyl acetate, methyl lactate, ethyl lactate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 2-hydroxyisobutyrate, and ethyl 2-hydroxyisobutyrate are preferred. propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, methanol, ethanol, isopropanol, n-butanol, isobutanol, tert-butanol, sec-butanol, diethylene glycol monomethyl ether, hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, tetradecamethylhexasiloxane, octamethylcyclotetrasiloxane, octamethylcyclopentasiloxane, 1,3-bis(trifluoromethyl)benzene, CF 13 CH2CH3, C6F 13 H, 1,1,2,2,3,3,4-heptafluorocyclopentane, 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, 1,3-bis(trifluoromethyl)benzene, CF3CH2OH, CF3CF2CH2OH, (CF3)2CHOH, perfluoropropyl methyl ether, perfluorobutyl methyl ether, perfluorobutyl ethyl ether, perfluorohexyl methyl ether, CF3CH2OCF2CHF2, CF3CH=CHCl, and CHF2CF=CHCl are preferred.

[0397] The silicone oil is not particularly limited, but examples thereof include silicone oils 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:

[0398] Above R 3a are each independently a hydrogen atom or a hydrocarbon group. Such hydrocarbon groups may be substituted.

[0399] 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.

[0400] R 3a are each independently preferably C optionally substituted by a halogen atom. 1-6 an alkyl or aryl group, more preferably C 1-6 It is an alkyl group or an aryl group.

[0401] Above C 1-6 The alkyl group may be straight-chain or branched, but is preferably straight-chain. C 1-6 The alkyl group is preferably C 1-3 It is preferably an alkyl group, more preferably a methyl group.

[0402] The aryl group is preferably a phenyl group.

[0403] 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.

[0404] In another embodiment, R 3a is a phenyl group.

[0405] In another embodiment, R 3a is a methyl group or a phenyl group, preferably a methyl group.

[0406] Above R 1a are each independently a hydrogen atom or a hydrocarbon group, and 3a It has the same meaning as:

[0407] R 1a are each independently preferably C optionally substituted by a halogen atom. 1-6 an alkyl or aryl group, more preferably C 1-6 It is an alkyl group or an aryl group.

[0408] 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.

[0409] In another embodiment, R 1a is a phenyl group.

[0410] In another embodiment, R 1a is a methyl group or a phenyl group, preferably a methyl group.

[0411] The above-mentioned a1 is 2 to 1500. a1 is 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 is 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.

[0412] a1 may be preferably 5 to 1000, more preferably 10 to 500, even more preferably 15 to 200, and even more preferably 15 to 150.

[0413] 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 is a divalent siloxane-containing group, and X in formula (1) D It has the same meaning as the divalent siloxane-containing group in the above formula.] Examples of the compound include compounds represented by the following formula:

[0414] The silicone oil may have an average molecular weight of 500 to 1,000,000, preferably 1,000 to 100,000. The molecular weight of the silicone oil can be measured using GPC.

[0415] Examples of the silicone oil include -(SiR 3a 2-O) a1Linear or cyclic silicone oils with a1 of 30 or less can be used. The linear silicone oils may be so-called straight silicone oils or modified silicone oils. Examples of straight silicone oils include dimethyl silicone oil, methylphenyl silicone oil, and methylhydrogen silicone oil. Examples of modified silicone oils include straight silicone oils modified with alkyl, aralkyl, polyether, higher fatty acid ester, fluoroalkyl, amino, epoxy, carboxyl, alcohol, etc. Examples of cyclic silicone oils include cyclic dimethylsiloxane oil.

[0416] The silicone oil may be contained in an amount of, for example, 0 to 50% by mass, preferably 0.001 to 30% by mass, and more preferably 0.1 to 5% by mass, relative to the composition of the present disclosure.

[0417] 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 a total of 100 parts by mass of the compounds of the present disclosure (if there are two or more types, the total of these, the same applies hereinafter).

[0418] The silicone oil contributes to improving the surface slipperiness of the surface treatment layer.

[0419] Examples of the alcohols include methanol, ethanol, isopropanol, n-butanol, isobutanol, tert-butanol, sec-butanol, 3-pentanol, octyl alcohol, 3-methyl-3-methoxybutanol, and tert-amyl alcohol. Addition of these alcohols to the composition improves the stability of the composition.

[0420] 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.

[0421] Examples of the aliphatic amine compounds include diethylamine, triethylamine, etc. Examples of the aromatic amine compounds include aniline, pyridine, etc.

[0422] 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 using a transition metal 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.

[0423] The hydrolyzable group means a group that can undergo a hydrolysis reaction, similar to the hydrolyzable group in the above-mentioned compound, that is, a group that can be separated from a transition metal atom by a hydrolysis reaction. 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.

[0424] In a preferred embodiment, the hydrolyzable group is -OR mBy using an alkoxy group as the hydrolyzable group, transition metal atoms 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.

[0425] In one embodiment, the hydrolyzable group may be the same as the hydrolyzable group contained in the compound described above. By using the same hydrolyzable group in the compound and the transition metal compound, even if the hydrolyzable groups are exchanged with each other, the effect can be reduced.

[0426] In another embodiment, the hydrolyzable group may be different from the hydrolyzable group contained in the compound. By making the hydrolyzable groups in the compound and the transition metal compound different, the hydrolysis reactivity can be controlled.

[0427] In one embodiment, the hydrolyzable group and the hydrolyzable group contained in the compound may be interchangeable in the composition.

[0428] In a preferred embodiment, the transition metal compound is Ta(OR m )5(wherein, R m is a substituted or unsubstituted C 1-4 is an alkyl group.), preferably Ta(OCH2CH3)5 or Si(OR m ) 1-m1 R m’ m1 (In the formula, R m is a substituted or unsubstituted C 1-4 is an alkyl group, and R m’ is C 1-4 is an alkyl group, and m1 is 0 or 1.) and can be preferably tetraethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, tetraisopropoxysilane, dimethyldiethoxysilane, or dimethyldimethoxysilane.

[0429] The catalyst may be contained in an amount of, for example, 0.0002% by mass or more relative to the total composition. The catalyst is preferably contained in an amount of 0.02% by mass or more, more preferably 0.04% by mass or more, relative to the total composition. The catalyst may be contained in an amount of, for example, 10% by mass or less, particularly 1% by mass or less, relative to the total composition. The composition of the present disclosure may contribute to the formation of a more durable surface treatment layer by containing the catalyst in the above-mentioned concentration.

[0430] 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.

[0431] 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.

[0432] In addition to the above, other components include, for example, tetraethoxysilane, methyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, and methyltriacetoxysilane.

[0433] 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.

[0434] In one embodiment, the compositions of the present disclosure are for dry coating processes, preferably vacuum deposition.

[0435] In one embodiment, the compositions of the present disclosure are for use in wet coating methods, preferably dip coating.

[0436] 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.

[0437] The composition of the present disclosure is preferably used as a surface treatment agent or as a component of a surface treatment agent.

[0438] The articles of the present disclosure are described below.

[0439] 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.

[0440] 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 common 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.

[0441] For example, if 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. Furthermore, if 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 or a multilayer. Examples of inorganic materials that can be used for the antireflection layer include SiO2, SiO, ZrO2, TiO2, TiO, Ti2O3, Ti2O5, Al2O3, Ta2O5, Ta3O5, Nb2O5, HfO2, Si3N4, CeO2, MgO, Y2O3, SnO2, MgF2, and WO3. These inorganic materials may be used alone or in combination (e.g., as a mixture) of two or more of them. When a multilayer antireflection layer is used, it is preferable to use SiO2 and / or SiO for the outermost layer. When the product to be manufactured is an optical glass component for a touch panel, a transparent electrode, such as a thin film made of indium tin oxide (ITO) or indium zinc oxide, may be provided on a portion of the surface of the substrate (glass). Furthermore, the substrate may have an insulating layer, an adhesive layer, a protective layer, a decorative frame layer (I-CON), an atomizing film layer, a hard coating film layer, a polarizing film, a phase difference film, a liquid crystal display module, etc., depending on the specific specifications.

[0442] 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 depending on the application and specific specifications of the product to be manufactured.

[0443] In one embodiment, the substrate may be made of a material whose surface originally contains hydroxyl groups. Examples of such materials include glass, metals (especially base metals), ceramics, and semiconductors, which form natural or thermal oxide films on their surfaces. Alternatively, for materials such as resins, which do not have sufficient hydroxyl groups or do not originally contain hydroxyl groups, pretreatment can be performed to introduce or increase the number of hydroxyl groups on the substrate surface. Examples of such pretreatments 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 used to clean the substrate surface (remove foreign matter, etc.). Another example of such pretreatment is a method in which an interfacial adsorbent having carbon-carbon unsaturated bond groups is first formed in the form of a monomolecular film on the substrate surface by the Langmuir-Blodgett method (LB method) or chemical adsorption, followed by cleavage of the unsaturated bonds in an atmosphere containing oxygen, nitrogen, or the like.

[0444] In another embodiment, the substrate may have at least a surface portion made of a material containing another reactive group, such as a silicone compound having one or more Si—H groups, or an alkoxysilane.

[0445] In a preferred embodiment, the substrate is glass, such as sapphire glass, soda-lime glass, alkali aluminosilicate glass, borosilicate glass, alkali-free glass, crystal glass, quartz glass, and crystallized glass, with chemically strengthened soda-lime glass, chemically strengthened alkali aluminosilicate glass, and chemically bonded borosilicate glass being particularly preferred.

[0446] 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, adhesion between the glass and the surface treatment layer is improved, and durability is improved.

[0447] In a preferred embodiment, the intermediate layer may contain an alkali metal in addition to silicon oxide.

[0448] Examples of the alkali metal include lithium, sodium, potassium, etc. The alkali metal is preferably sodium.

[0449] 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 the intermediate layer in improving adhesiveness becomes greater.

[0450] The alkali metal atom concentration in the intermediate layer can be measured by various surface analysis devices, such as TOF-SIMS, XPS, and XRF.

[0451] The proportion of alkali metal atoms in the total atoms of the entire intermediate layer can be obtained by XPS depth profile analysis 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.

[0452] The average alkali metal concentration in the intermediate layer in a region 1 nm or less deep from the surface in contact with the surface treatment layer is determined by obtaining a depth profile of the alkali metal atom concentration by TOF-SIMS (time-of-flight secondary ion mass spectrometry) depth profile analysis using ion sputtering, and then calculating the average alkali metal atom concentration in the profile. TOF-SIMS depth profile analysis using 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.

[0453] 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.

[0454] 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 a substrate so as to coat the surface. The coating method is not particularly limited. For example, a wet coating method or a dry coating method can be used.

[0455] 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 similar methods.

[0456] Examples of dry coating methods include vapor deposition (usually vacuum deposition), sputtering, CVD, and similar methods. Specific examples of vapor deposition methods (usually vacuum deposition) include resistance heating, electron beam, high frequency heating using microwaves, ion beam, and similar methods. Specific examples of CVD methods include plasma-CVD, optical CVD, thermal CVD, and similar methods.

[0457] Furthermore, coating by atmospheric pressure plasma method is also possible.

[0458] When using the wet coating method, the surface treatment agent of the present disclosure can 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, carbohydrate acetate, etc. Esters such as ethanol, diethyl oxalate, ethyl pyruvate, ethyl 2-hydroxybutyrate, ethyl acetoacetate, amyl acetate, methyl lactate, ethyl lactate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 2-hydroxyisobutyrate, and ethyl 2-hydroxyisobutyrate; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, 2-hexanone, cyclohexanone, methyl amino ketone, and 2-heptanone; 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., CF; 13 CH2CH3 (e.g., Asahiklin (registered trademark) AC-6000 manufactured by Asahi Glass Co., Ltd.), CF 13H (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; CF3CH2OH, C fluorine-containing alcohols such as FCFCHOH and (CF)CHOH; hydrofluoroethers (HFE) (for example, perfluoropropyl methyl ether (CFOCH) (for example, Novec (trademark) 7000 manufactured by Sumitomo 3M Limited), perfluorobutyl methyl ether (CFOCH) (for example, Novec (trademark) 7100 manufactured by Sumitomo 3M Limited), perfluorobutyl ethyl ether (CFOCH) (for example, Novec (trademark) 7200 manufactured by Sumitomo 3M Limited), alkyl perfluoroalkyl ethers (the perfluoroalkyl group and alkyl group may be linear or branched) such as perfluorohexyl methyl ether (C2F5CF(OCH3)C3F7) (e.g., Novec (trademark) 7300 manufactured by Sumitomo 3M Limited), or CF3CH2OCF2CHF2 (e.g., Asahiklin (registered trademark) AE-3000 manufactured by Asahi Glass Co., Ltd.), hydrofluoroolefins; CF3CH=CHCl (e.g., CELEFIN (registered trademark) manufactured by Central Glass Co., Ltd.), 1233Z), CHFCF=CHCl (for example, AMOLEA (registered trademark) AS-300 manufactured by Asahi Glass Co., Ltd.), ethers such as cyclopentyl methyl ether; siloxanes such as hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, octamethylcyclotetrasiloxane, octamethylcyclopentasiloxane, decamethylcyclopentasiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, and tetradecamethylhexasiloxane; dimethyl sulfoxide, etc. Alternatively, mixed solvents of two or more of these may be used.Among these, aliphatic hydrocarbons, aromatic hydrocarbons, esters, glycol ethers, alcohols, ether alcohols, and siloxanes are preferred. For example, hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, mineral spirits, benzene, toluene, xylene, naphthalene, methyl acetate, ethyl acetate, propyl acetate, n-butyl acetate, isopropyl acetate, isobutyl acetate, cellosolve acetate, propylene glycol methyl ether acetate, carbitol acetate, diethyl oxalate, ethyl pyruvate, ethyl 2-hydroxybutyrate, ethyl acetoacetate, amyl acetate, methyl lactate, ethyl lactate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 2-hydroxyisobutyrate, and ethyl 2-hydroxyisobutyrate are preferred. propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, methanol, ethanol, isopropanol, n-butanol, isobutanol, tert-butanol, sec-butanol, diethylene glycol monomethyl ether, hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, tetradecamethylhexasiloxane, octamethylcyclotetrasiloxane, octamethylcyclopentasiloxane, 1,3-bis(trifluoromethyl)benzene, CF 13 CH2CH3, C6F 13 H, 1,1,2,2,3,3,4-heptafluorocyclopentane, 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, 1,3-bis(trifluoromethyl)benzene, CF3CH2OH, CF3CF2CH2OH, (CF3)2CHOH, perfluoropropyl methyl ether, perfluorobutyl methyl ether, perfluorobutyl ethyl ether, perfluorohexyl methyl ether, CF3CH2OCF2CHF2, CF3CH=CHCl, and CHF2CF=CHCl are preferred.

[0459] In one embodiment, when using the wet coating method, the solvent is, for example, R 90 A compound represented by —OH can be used. 90 is a monovalent organic group, preferably C 1-20 Alkyl group or C 3-20 The alkylene group may be substituted with one or more substituents, such as a hydroxyl group, -OR 91 (where R 91 is C 1-10 Alkyl groups, preferably C 1-3 alkyl groups, such as methyl groups.

[0460] 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.

[0461] The layer formation of the surface treatment agent is preferably carried out so that the surface treatment agent of the present disclosure is present in the layer together with a catalyst for hydrolysis and dehydration condensation. Conveniently, in the case of a 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 a dry coating method, the surface treatment agent of the present disclosure to which the catalyst has been added may be directly subjected to vapor deposition (usually vacuum deposition), or a pellet-shaped material impregnated with the surface treatment agent of the present disclosure to which the catalyst has been added may be subjected to vapor deposition (usually vacuum deposition) on a porous metal such as iron or copper.

[0462] 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 its 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. Examples of acid catalysts that can be used include acetic acid, formic acid, trifluoroacetic acid, hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, sulfonic acid, methanesulfonic acid, p-toluenesulfonic acid, etc. Examples of base catalysts that can be used include ammonia, sodium hydroxide, potassium hydroxide, and organic amines such as triethylamine and diethylamine. Examples of transition metals, aliphatic amine compounds, and aromatic amine compounds are the same as those described above.

[0463] 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 stains such as fingerprints), waterproof properties (for example, preventing water penetration into electronic components), surface slipperiness (or lubricity, for example, ease of wiping off stains such as fingerprints and excellent tactile feel), chemical resistance, etc., depending on the composition of the surface treatment agent used, and can be suitably used as a functional thin film.

[0464] Therefore, the present disclosure also relates to an optical material having the above-described surface treatment layer as the outermost layer.

[0465] Preferred examples of the optical material include optical materials related 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 EL displays, inorganic thin-film EL dot matrix displays, rear projection displays, vacuum fluorescent displays (VFDs), and field emission displays (FEDs), or protective plates for such displays, or displays whose surfaces have been treated with an anti-reflection film.

[0466] The article of the present disclosure may be, but is not particularly limited to, an optical member. Examples of optical members include lenses for eyeglasses and the like; front protective 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 of optical discs such as Blu-ray (registered trademark) discs, DVD discs, CD-Rs, and MOs; optical fibers; and the display surfaces of watches and clocks.

[0467] The article of the present disclosure may also be a medical device or medical material. The article having a layer obtained by the present disclosure may also be an automobile interior or exterior component. Examples of exterior components include windows, light covers, and exterior camera covers. Examples of interior components include instrument panel covers, navigation system touch panels, and decorative interior components.

[0468] The thickness of the layer is not particularly limited. In the case of optical members, 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.

[0469] X-ray photoelectron spectroscopy (XPS) can be performed using an ULVAC-PHI PHI5000 VersaProbe II instrument to measure the atomic composition and atomic ratios of the surface treatment layer. XPS analysis conditions include a monochromated AlKα X-ray source at 25 W, a photoelectron detection area of ​​1400 μm × 300 μm, a photoelectron detection angle ranging from 20° to 90° (e.g., 20°, 45°, 90°), and a pass energy of 23.5 eV. Gas cluster ion beams or Ar ions can be used for sputtering. Using the above instrument 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 intermediate layer.

[0470] Depth analysis can also be performed. Measurement conditions for XPS analysis include a monochromated AlKα X-ray source at 25 W, a photoelectron detection area of ​​1400 μm × 300 μm, a photoelectron detection angle in the range of 20 to 90 degrees (e.g., 20, 45, and 90 degrees), and a pass energy of 23.5 eV. Ar ions, gas cluster ions, and C ions can be used as sputtering ions. Sputtering can be used to etch 1 to 100 nm, and the composition of the coating at each etching depth can be determined.

[0471] The detection depth can be adjusted appropriately by adjusting the photoelectron detection angle in the XPS analysis. For example, a shallow angle of approximately 20 degrees can achieve a detection depth of approximately 3 nm, while a deep angle of approximately 90 degrees can achieve a detection depth of approximately 10 nm.

[0472] 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.

[0473] 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 its partial condensates can be converted into silicon oxide by dehydration condensation. Alkali metal silicates can be converted into silicic acid or its partial condensates by the addition of an acid or a cation exchange resin, and the resulting silicic acid or its partial condensates can then be dehydration condensed into silicon oxide. Examples of the hydrolyzable group in a silane compound having a hydrolyzable group bonded to a silicon atom include an alkoxy group and a chlorine atom. The hydrolyzable group in the silane compound can be hydrolyzed to a hydroxyl group, and the resulting silanol compound can be dehydration condensed to form silicon oxide. Examples of silane compounds having a hydrolyzable group bonded to a silicon atom include alkoxysilanes such as tetraalkoxysilanes and alkyltrialkoxysilanes, and tetrachlorosilane.

[0474] Examples of the alkali metal source include alkali metal hydroxides, water-soluble alkali metal salts, etc. Examples of the water-soluble alkali metal salts include alkali metal carbonates, alkali metal hydrogencarbonates, alkali metal hydrochlorides, alkali metal nitrates, etc. As the alkali metal source, alkali metal hydroxides and alkali metal carbonates are preferred.

[0475] Alkali metal silicates can be used as silicon oxide precursors and alkali metal sources. Alkali metal silicates can be converted to silicon oxide via silicic acid, but a small amount of alkali metal may remain in the resulting silicon oxide. Therefore, by adjusting the amount of the remaining alkali metal, silicon oxide containing a desired amount of alkali metal atoms can be obtained.

[0476] 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 even more preferably 3 to 10 nm.

[0477] The compounds, compositions, and articles of the present disclosure have been described in detail above. However, the compounds, compositions, and articles of the present disclosure are not limited to those exemplified above. [Example]

[0478] The compounds of the present disclosure will be described below in examples, but the present disclosure is not limited to the following examples.

[0479] (Synthesis Example 1) 3.00 g of 4-(trifluoromethoxy)phenylacetic acid, 20 g of tetrahydrofuran, 2.93 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 0.16 g of 4-dimethylaminopyridine, and 2.34 mL of 9-decen-1-ol were added and stirred overnight at room temperature. After purification, the following trifluoromethoxy group-containing compound (1) CF3OC6H4CH2COO(CH2)7CH2CH=CH2 (4.50 g) was obtained.

[0480] 1 H NMR(CDCl3,400MHz)δ[ppm]:1.241-1.388(m),1.576-1.645(t),2.009-2.077(m),3.617(s ),4.072-4.107(t),4.916-5.023(m),5.760-5.862(m),7.162-7.180(m),7.293-7.322(m)

[0481] Trifluoromethoxy group-containing compounds (1) [ka]

[0482] (Synthesis Example 2) 2.58 g of the trifluoromethoxy group-containing compound (1) CF3OC6H4CH2COO(CH2)7CH2CH=CH2 obtained in Synthesis Example 1, 7.5 g of toluene, 0.046 g of triacetoxymethylsilane, and 0.35 ml of a xylene solution containing 2% Pt complex of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane were added, followed by 1.41 mL of trichlorosilane, heating to 60°C and stirring for 3 hours. After distilling off the volatiles under reduced pressure, a mixed solution of 0.67 g of methanol and 14.80 g of trimethyl orthoformate was added, heating to 65°C and stirring for 2 hours. Purification was then performed to obtain the following compound (2) CF3OC6H4CH2COO(CH2) 10 Si(OCH3)3 (2.54 g) was obtained.

[0483] 1 H NMR(CDCl3,400MHz)δ[ppm]:0.628-0.669(m),1.255-1.428(m),1.589-1.623 (m),3.569(s),3.614(s),4.068-4.102(t),7.157-7.178(m),7.290-7.325(m)

[0484] Trifluoromethoxy group-containing compounds (2) [ka]

[0485] (Synthesis Example 3) 9.825 g of 4-(trifluoromethoxy)aniline, 5 g of toluene, 5.97 g of 1,5,7-triazabicyclo[4.4.0]dec-5-ene, and 5.62 ml of methyl 10-undecenoate were added, heated to 100°C, and stirred for 30 hours. After purification, the following trifluoromethoxy group-containing compound (3) CF3OC6H4NHCO(CH2)7CH2CH=CH2 (8.03 g) was obtained.

[0486] 1H NMR(CDCl3,400MHz)δ[ppm]:1.275-1.380(m),1.591-1.646(m),1.677-1.751(m),2.004-2.06 0(m),2.324-2.372(m),4.909-5.016(m),5.751-5.857(m),7.151-7.172(d),7.532-7.555(d)

[0487] Trifluoromethoxy group-containing compounds (3) [ka]

[0488] (Synthesis Example 4) 2.58 g of the trifluoromethoxy group-containing compound (3) CF3OC6H4NHCO(CH2)7CH2CH=CH2 obtained in Synthesis Example 3, 7.74 g of toluene, 0.05 g of triacetoxymethylsilane, and 0.38 ml of a xylene solution containing 2% Pt complex of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane were added, followed by 1.52 ml of trichlorosilane, heating to 60°C and stirring for 3 hours. After distilling off the volatiles under reduced pressure, a mixed solution of 0.72 g of methanol and 15.95 g of trimethyl orthoformate was added, heating to 65°C and stirring for 2 hours. Purification was then performed to obtain the following compound (4) CF3OC6H4NHCO(CH2) 10 Si(OCH3)3 (3.07 g) was obtained.

[0489] 1 H NMR(CDCl3,400MHz)δ[ppm]:0.617-0.657(m),1.257-1.412(m),1.600-1.636(m) ,1.668-1.722(m),2.313-2.364(m)3.561(s),7.142-7.164(d),7.535-7.557(d)

[0490] Trifluoromethoxy group-containing compounds (4) [ka]

[0491] (Synthesis Example 5) 5.19 g of 16-hydroxyhexadecanoic acid, 35.0 ml of toluene, and 35.0 ml of methanol were added, and then 41.28 ml of a 10% hexane solution of trimethylsilyldiazomethane was added in an ice bath and stirred at room temperature for 1 hour. After that, purification was carried out to obtain the following methyl ester group-containing alcohol compound (5) HO(CH2) 15 COOCH3 (5.40 g) was obtained.

[0492] 1 H NMR(CDCl3,400MHz)δ[ppm]:1.220-1.331(m),1.525-1.628(m),2.276-2.314(t),3.618-3.651(t),3.659(s)

[0493] Methyl ester group-containing alcohol compounds (5) [ka]

[0494] (Synthesis Example 6) Methyl ester group-containing alcohol compound (5) HO(CH2) obtained in Synthesis Example 5 15 5.50 g of COOCH3, 50.7 g of tetrahydrofuran, 1.15 g of sodium hydride, and 2.92 g of carbon disulfide were added and stirred at room temperature for 3 hours. Subsequently, 4.09 g of iodomethane was added and stirred at room temperature for 2 hours. After that, purification was carried out to obtain the following xanthate group-containing compound (6) CH3SC(S)O(CH2) 15 COOCH3 (6.11 g) was obtained.

[0495] 1 H NMR(CDCl3,400MHz)δ[ppm]:1.252-1.401(m),1.594-1.631(m),1.774-1.812(m),2.280-2.317(t),2.554(s),3.663(s),4.569-4.602(t)

[0496] Xanthate group-containing compounds (6) [ka]

[0497] (Synthesis Example 7) Xanthate group-containing compound (6) obtained in Synthesis Example 6, CH3SC(S)O(CH2) 15 3.03 g of COOCH3, 48.0 ml of dichloromethane, and 10.44 g of 1,3-dibromo-5,5-dimethylhydantoin were added and stirred at -78°C for 30 minutes. Next, 7.63 g of pyridinium poly(hydrogen fluoride) was added and stirred at -78°C for 1 hour and at room temperature for 5 hours. After purification, the following trifluoromethoxy group-containing compound (7) CFO(CH2) 15 COOCH3 (2.53 g) was obtained.

[0498] 1 H NMR(CDCl3,400MHz)δ[ppm]:1.243-1.382(m),1.568-1.700(m),2.271-2.308(t),3.653(s),3.917-3.949(t)

[0499] Trifluoromethoxy group-containing compounds (7) [ka]

[0500] (Synthesis Example 8) Trifluoromethoxy group-containing compound (7) CF3O(CH2) obtained in Synthesis Example 7 15 1.12 g of COOCH3, 0.53 g of 1,5,7-triazabicyclo[4.4.0]dec-5-ene, and 9.02 g of allylamine were added, heated to 65°C, and stirred for 6 hours. After purification, the following trifluoromethoxy group-containing compound (8) CF3O(CH2) 15CONHCH2CH=CH2 (1.05 g) was obtained.

[0501] 1 H NMR(CDCl3,400MHz)δ[ppm]:1.250-1.391(m),1.598-1.710(m),2.169-2.208(t), 3.875-3.888(t),3.927-3.960(t),5.116-5.202(m),5.456(brs),5.792-5.889(m)

[0502] Trifluoromethoxy group-containing compounds (8) [ka]

[0503] (Synthesis Example 9) Trifluoromethoxy group-containing compound (8) CF3O(CH2) obtained in Synthesis Example 8 15 1.05g of CONHCH2CH=CH2, 3.15g of toluene, 0.02g of triacetoxymethylsilane, and 0.14ml of a xylene solution containing 2% Pt complex of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane were added, followed by 0.56ml of trichlorosilane, which was heated to 60°C and stirred for 3 hours. After distilling off the volatiles under reduced pressure, a mixed solution of 0.27g of methanol and 5.87g of trimethyl orthoformate was added, heated to 65°C, and stirred for 2 hours. Purification was then carried out to obtain the following compound (9)CF3O(CH2) with a terminal trimethoxysilyl group. 15 CONH(CH2)3Si(OCH3)3 (1.17 g) was obtained.

[0504] 1 H NMR(CDCl3,400MHz)δ[ppm]:0.620-0.661(m),1.242-1.384(m),1.591-1.686(m),2.117-2.156(t),3.211-3.261(q),3.563(s),3.919-3.952(t)

[0505] Compounds containing terminal trimethoxysilyl groups (9) [ka]

[0506] (Surface treatment agent 1) The compound (9) obtained above was diluted to a concentration of 10 wt % in 1,3-bis(trifluoromethyl)benzene, to obtain a surface treatment agent 1.

[0507] (Synthesis Example 10) 3.0 g of trifluoroethanol, 3.0 g of 18-bromo-1-octadecene, 1.5 g of 24% aqueous potassium hydroxide solution, 0.4 g of tetrabutylammonium bromide, and 0.5 g of diglyme were added and stirred under reflux for 24 hours. After that, purification was carried out to obtain the following 1,1,1-trifluoroethoxy group-containing compound (10) CF3CH2O(CH2) 16 CH=CH2 (2.8 g) was obtained.

[0508] 1 H NMR(CDCl3,400MHz)δ[ppm]:1.110-1.1.432(m),1.565-1.646(m),2.009-2.0 65(q),3.575-3.608(t),3.764-3.829(q),4.908-5.019(m),5.763-5.865(m)

[0509] Trifluoroethoxy group-containing compounds (10) [ka]

[0510] (Synthesis Example 11) Trifluoroethoxy group-containing compound (10) CF3CH2O(CH2) obtained in Synthesis Example 10 16A mixture of 1.0 g of CH═CH₂, 3.0 g of toluene, 0.02 g of triacetoxymethylsilane, 0.2 ml of a xylene solution containing 2% Pt complex of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, and 1.2 ml of trichlorosilane was heated to 55°C and stirred for 3 hours. After distilling off the volatiles under reduced pressure, a mixed solution of 0.1 g of methanol and 1.8 g of trimethyl orthoformate was added, and the mixture was heated to 60°C and stirred for 3 hours. Purification was then carried out to obtain the following compound (11) CF₃CH₂O(CH₂) with a terminal trimethoxysilyl group. 18 Si(OCH3)3 (1.74 g) was obtained.

[0511] 1 H NMR(CDCl3,400MHz)δ[ppm]:0.604-0.668(m),1.195-1.434(m),1.554-1.624(m),3.521-3.611(m),3.751-3.817(q)

[0512] Trifluoroethoxy group-containing compounds (11) [ka]

[0513] (Surface treatment agent 2) The compound (11) obtained above was diluted to a concentration of 10 wt % in hexamethyldisiloxane, thereby obtaining a surface treatment agent 2.

[0514] (Surface treatment agent 3) Compound (X)CH3(CH2) 16 CONH(CH2)3Si(OCH3)3 was diluted to a 10 wt % ethanol solution to obtain surface treatment agent 3.

[0515] (Formation of surface treatment layer) (Examples 1 and 2, and Comparative Example 1) The surface treatment agents 1 to 3 prepared above were vacuum-deposited onto chemically strengthened glass (Corning Gorilla Glass, thickness 0.7 mm). Specifically, 0.1 g of the surface treatment agent was placed in a molybdenum boat in a vacuum deposition apparatus, and the pressure in the vacuum deposition apparatus was set to 3.0 × 10- 3 The chamber was evacuated to below 100 Pa. A silicon dioxide film with a thickness of 7 nm was then formed, and the boat was then heated using a resistance heating method to form a surface treatment layer. This was followed by a heat treatment in an oven at 150°C for 2 hours, yielding a surface treatment layer.

[0516] <Evaluation> [Oil repellency evaluation] After the surface treatment layer was formed, the excess was wiped off, and then the static contact angle of normal hexadecane was measured. The contact angle was measured in a 25°C environment using a fully automatic contact angle meter, DropMaster 700 (manufactured by Kyowa Interface Science Co., Ltd.). Specifically, the substrate having the surface treatment layer to be measured was placed horizontally, and hexadecane was dropped onto the surface from a microsyringe. A still image was taken with a video microscope one second after the drop, and the static contact angle was measured. The static contact angle was measured at five different points on the surface treatment layer of the substrate, and the average value was calculated. The results are shown in Table 1.

[0517] [Table 1] [Industrial Applicability]

[0518] The compounds of the present disclosure may be suitably utilized in a wide variety of applications.

Claims

1. The following formula (1): 【Chemistry 1】 [In the formula: Rf １ are each independently terminated with CF ３ is a group having the formula However, the terminal CF ３ is adjacent to CF ２ Without X Ａ are each independently a single bond, an oxygen atom, or a divalent to decavalent organic group, R Ｓｉ is a monovalent group containing a Si atom to which a hydroxyl group or a hydrolyzable group is bonded, α1 is an integer from 1 to 9; and α2 is an integer from 1 to 9. A fluorine-containing silane compound represented by the formula:

2. Rf １ are each independently R Ａ１ -X Ｂ - [In the formula: 10 Ａ１ は、9 ３ 0、9 ３ 10、40 ３ N00、6 ３ 10 ２ N00、(S0 ３ ) ２ 90、(40) ３ 10 ２ ) ２ 90、40 ３ SU、S ３ 1000000 ３ 10 ２ 1000000 ３ 1000000 ３ 10 ２ 10(00000)、6 ３ ROY000000 ３ 10 ２ ROY000000 ３ NHYY、9 ３ 10 ２ NHYY、9 ３ 10(40) ３ 0、40 ３ 10 ２ 10(40) ３ 0、40 ３ ROY(S ２ 9. The ３ 0、40 ３ 10 ２ ROY(S ２ 9. The ３ 0、(40) ３ ) ２ DAYまたは(10). ３ 10 ２ ) ２ LIKEであり、 X Ｂ teeth, single bond, a group containing a divalent siloxane group, or -(CFH) ａ１ -(CH ２ ) ｂ１ -(O) ｃ１ -(C(R Ａ２ ) ｅ１ H ２－ｅ１ ) ｄ１ -(NR Ａ３ ) ｆ１ - (In the formula: R Ａ２ is a monovalent group having CF ３ -, CF ３ O-, CF ３ NH-, CF ３ CH ２ NH-, (CF ３ ) ２ N-, (CF ３ CH ２ ) ２ N-, CF ３ S-, CF ３ C(=O)-, CF ３ CH ２ C(=O)-, CF ３ C(=O)O-, CF ３ CH ２ OC(=O)-, CF ３ CONH-, CF ３ CH ２ CONH-, CF ３ NHCO-, CF ３ CH ２ NHCO-, CF ３ CON(CF ３ )-, CF ３ CH ２ CON(CF ３ )-, CF ３ CON(CH ２ CF ３ )-, CF ３ CH ２ CON(CH ２ CF ３ )-, (CF ３ ) ２ NCO- or (CF ３ CH ２ ) ２ NCO-. R Ａ３ is a hydrogen atom or CF ３ -, CF ３ O-, CF ３ NH-, CF ３ CH ２ NH-, (CF ３ ) ２ N-, (CF ３ CH ２ ) ２ N-, CF ３ S-, CF ３ C(=O)-, CF ３ CH ２ C(=O)-, CF ３ C(=O)O-, CF ３ CH ２ OC(=O)-, CF ３ CONH-, CF ３ CH ２ CONH-, CF ３ NHCO-, CF ３ CH ２ NHCO-, CF ３ CON (CF ３ ) -, CF ３ CH ２ CON (CF ３ ) -, CF ３ CON (CH ２ CF ３ ) -, CF ３ CH ２ CON (CH ２ CF ３ ) -, (CF ３ ) ２ NCO- or (CF ３ CH ２ ) ２ is a monovalent group having NCO—, a1 is an integer from 0 to 200, b1 is an integer from 0 to 200, c1 is an integer from 0 to 200, d1 is an integer from 0 to 200, e1 is 1 or 2, f1 is an integer from 0 to 200, The repeating units enclosed in parentheses and designated by the symbols a1, b1, c1, d1, and f1 may be present in any order. is a group represented by the following formula: The fluorine-containing silane compound according to claim 1, wherein the fluorine-containing silane compound is a group represented by the formula:

3. R Ａ１ is CF ３ O-, CF ３ NH-, or (CF ３ ) ２ The fluorine-containing silane compound according to claim 2, which is N-.

4. R Ａ２ is CF ３ O-, CF ３ NH-, or (CF ３ ) ２ The fluorine-containing silane compound according to claim 2 or 3, wherein the fluorine-containing silane compound is a monovalent group having N-.

5. R Ａ３ is a hydrogen atom or CF ３ The fluorine-containing silane compound according to any one of claims 2 to 4, wherein the fluorine-containing silane compound is a monovalent group having O-.

6. X Ｂ yes、-(CFH) ａ１ -(CH ２ ) ｂ１ -(O) ｃ１ - [In the formula: a1 is an integer from 0 to 200, b1 is an integer from 0 to 200, c1 is an integer from 0 to 10, The repeating units enclosed in parentheses and designated by the symbols a1, b1, and c1 may be present in any order.] The fluorine-containing silane compound according to claim 2 or 3, wherein the fluorine-containing silane compound is a group represented by the formula:

7. X Ｂ is -(CH ２ ) ｂ１ - [In the formula, b1 is an integer of 0 to 36.] The fluorine-containing silane compound according to claim 2 or 3, wherein the fluorine-containing silane compound is a group represented by the formula:

8. X Ｂ is -(CH ２ ) ｇ１ -R Ｓ -Si(R ５ ) ２ - (CH ２ ) ｇ１ - [In the formula: Each g1 is independently an integer of 0 to 30, R Ｓ is the following formula: 【Chemistry 2】 (In the formula: R ３ are each independently a single bond, C １－１２ alkylene group, -R ６ -O-R ６ -, -R ８ -R ７ -R ８ -, -R ８ -R ７ -R ９ -R ７ -R ８ -, -R ８ -R ７ -R ９ -R ６ -R ９ -R ７ -R ８ - or -R ９ -R ６ -R ９ -R ７ -R ９ -R ６ -R ９ - and R ４ are each independently C １－１２ alkylene group, -R ６ -O-R ６ -, -R ８ -R ７ -R ８ -, -R ８ -R ７ -R ９ -R ７ -R ８ -, -R ８ -R ７ -R ９ -R ６ -R ９ -R ７ -R ８ - or -R ９ -R ６ -R ９ -R ７ -R ９ -R ６ -R ９ - and R ６ are each independently C １－６ is an alkylene group, R ７ each independently represents an optionally substituted phenylene group or naphthylene group, R ８ are each independently 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 the following formula: The fluorine-containing silane compound according to claim 2 or 3, wherein the fluorine-containing silane compound is a group represented by the formula:

9. X Ａ is a single bond, -(X ５２ ) ｌ５ - or the formula (X Ａ１ ): 【Transformation 3】 [In the formula: X ５２ each independently represents an —O—, —S—, o-, m- or p-phenylene group, —CO—, —C(O)O—, —OC(O)—, or —CONR ５４ -, -NR ５４ CO-, -O-CONR ５４ -, -NR ５４ CO—O—, —NR ５４ CONR ５４ -, -NR ５４ -, and -(CH ２ ) ｎ５ - is a group selected from the group consisting of R ５４ are each independently a hydrogen atom or a monovalent organic group, n5 each independently represents an integer from 1 to 30; l5 is an integer from 1 to 10, X ａ are each independently a single bond or a divalent linking group. The fluorine-containing silane compound according to any one of claims 1 to 8, wherein the fluorine-containing silane compound is a group represented by the formula:

10. R Ｓｉ is represented by the following formula (S1), (S2), (S3), (S4) or (S5): 【Chemistry 4】 [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 ) units are each independently an integer from 0 to 3, X １１ are each independently a single bond or a divalent organic group, R １３ are each independently a hydrogen atom or a monovalent organic group, each t is independently an integer of 2 or greater; R １４ are each independently a hydrogen atom, a halogen atom or -X １１ -SiR １１ ｎ１ R １２ ３－ｎ１ and 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, R ａ１ are each independently -Z １ -SiR ２１ ｐ１ R ２２ ｑ１ R ２３ ｒ１ and Z １ are each independently a divalent organic group, R ２１ are each independently -Z １’ -SiR ２１’ ｐ１’ R ２２’ ｑ１’ R ２３’ ｒ１’ and R ２２ are each independently a hydroxyl group or a hydrolyzable group, R ２３ are each independently a monovalent organic group, p1 is independently an integer of 0 to 3, Each q1 is independently an integer of 0 to 3, Each r1 is independently an integer of 0 to 3, Z １’ are each independently a divalent organic group, R ２１’ are each independently -Z １” -SiR ２２” ｑ１” R ２３” ｒ１” and R ２２’ are each independently a hydroxyl group or a hydrolyzable group, R ２３’ are each independently a monovalent organic group, p1' is independently an integer of 0 to 3, Each q1' is independently an integer of 0 to 3, each r1' is independently an integer of 0 to 3; Z １” are each independently a divalent organic group, R ２２” are each independently a hydroxyl group or a hydrolyzable group, R ２３” are each independently a monovalent organic group, Each q1" is independently an integer of 0 to 3, each r1" is independently an integer of 0 to 3; R ｂ１ are each independently a hydroxyl group or a hydrolyzable group, R ｃ１ are each independently a monovalent organic group, Each k1 is independently an integer of 0 to 3, Each l1 is independently an integer of 0 to 3, m1 each independently represents an integer of 0 to 3; R ｄ１ are each independently -Z ２ -CR ３１ ｐ２ R ３２ ｑ２ R ３３ ｒ２ and Z ２ are each independently a single bond, an oxygen atom, or a divalent organic group, R ３１ are each independently -Z ２’ -CR ３２’ ｑ２’ R ３３’ ｒ２’ and R ３２ are each independently -Z ３ -SiR ３４ ｎ２ R ３５ ３－ｎ２ and R ３３ are each independently a hydrogen atom, a hydroxyl group, or a monovalent organic group, p2 is independently an integer of 0 to 3, Each q2 is independently an integer of 0 to 3, Each r2 is independently an integer of 0 to 3, Z ２’ are each independently a single bond, an oxygen atom, or a divalent organic group, R ３２’ are each independently -Z ３ -SiR ３４ ｎ２ R ３５ ３－ｎ２ and R ３３’ are each independently a hydrogen atom, a hydroxyl group, or a monovalent organic group, Each q2' is independently an integer of 0 to 3, each r2' is independently an integer of 0 to 3; Z ３ are each independently a single bond, an oxygen atom, or a divalent organic group; R ３４ are each independently a hydroxyl group or a hydrolyzable group, R ３５ are each independently a monovalent organic group, n2 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 are each independently a hydrogen atom, a hydroxyl group, or a monovalent organic group, k2 each independently represents an integer of 0 to 3; l2 is independently an integer of 0 to 3, Each m2 is independently an integer of 0 to 3. 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 are each independently a single bond, an oxygen atom, or a divalent organic group, k3 is 1 or 2; l3 is 0 or 1, However, in formula (S1), (S2), (S3), (S4), or (S5), there are at least two Si atoms to which a hydroxyl group or a hydrolyzable group is bonded.] The fluorine-containing silane compound according to claim 1, wherein the fluorine-containing silane compound is a group represented by the formula:

11. Rf １ is R Ａ１ -X Ｂ - and R Ａ１ is CF ３ - or CF ３ O-, X Ｂ is a single bond, X Ａ is -(p-phenylene) ｖ１ - (CH ２ ) ｖ２ -R ５７ ｖ３ - (CH ２ ) ｖ４ - and R ５７ is —CONH—, —NHCO—, —COO—, or —O—, v1 is 0 or 1, v2 is an integer from 0 to 20, v3 is 0 or 1, v4 is an integer from 2 to 20, R Ｓｉ is -SiR １１ ３ and R １１ is a methoxy group, α1 is 1, α2 is 1, The fluorine-containing silane compound according to claim 1 .

12. The following compound: The fluorine-containing silane compound according to claim 1 , selected from the group consisting of:

13. A surface treatment agent comprising the fluorine-containing silane compound according to any one of claims 1 to 12.

14. The surface treatment agent according to claim 11, further comprising a condensate of the fluorine-containing silane compound according to any one of claims 1 to 12.

15. Furthermore, R ９０ —OH (where R ９０ The surface treatment agent according to claim 13 or 14, comprising an alcohol represented by the following formula:

16. The surface treatment agent according to any one of claims 13 to 15, which is for vacuum deposition.

17. The surface treatment agent according to any one of claims 13 to 15, which is for wet coating.

18. A pellet containing the surface treatment agent according to any one of claims 13 to 17.

19. An article comprising a substrate and a layer formed on the substrate from the fluorine-containing silane compound according to any one of claims 1 to 12.

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.

23. The article according to any one of claims 19 to 22, which is an optical element.

24. 24. The article of claim 23, which is a display.

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