Fluorosilicone compound

Abstract

To provide a fluorosilicone compound with excellent releasability.SOLUTION: The present invention provides a fluorosilicone compound represented by formula (I) (where the symbols in the formula are as defined in the description).SELECTED DRAWING: None

Description

[Technical field]

[0001] The present disclosure relates to fluorosilicone compounds. [Background technology]

[0002] Fluorine-containing silicone compounds have been known and are used, for example, as release agents for molding various rubbers and resins (see Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Special Publication No. 2009-541498 Summary of the Invention [Problem to be solved by the invention]

[0004] An object of the present disclosure is to provide a fluorosilicone compound having excellent mold releasability. [Means for solving the problem]

[0005] [1] Formula (I): [ka] [In formula: R A 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-, R 1 , R 2, R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group; R 3 and R 10 each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, R A -X-, or R Si -Y-, X and Y are each independently a divalent organic group; R Si is a monovalent group containing a Si atom having a hydroxyl group or a hydrolyzable group bonded thereto, m is an integer from 1 to 100; n is an integer from 1 to 50; o is an integer from 0 to 200; The repeating units enclosed in parentheses with m, n, and o may occur in any order.] A fluorosilicone compound represented by the formula: [2] R A The fluorosilicone compound according to the above [1], wherein is CF3O-, CF3NH-, or (CF3)2N-. [3] R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are each independently 1-4 The fluorosilicone compound according to the above [1] or [2], which is an alkyl group. [4] R 3 and R 10 are each independently 1-4 The fluorosilicone compound according to any one of the above [1] to [3], which is an alkyl group. [5] X is -(Ar) a1 -(CFH) b1-(CH2) c1 -(O) d1 - [In formula: Ar is a fluorine atom or R A is a divalent aromatic group optionally substituted by a1 is an integer from 0 to 10, b1 is an integer from 0 to 200, c1 is an integer from 0 to 200, d1 is an integer from 0 to 10, The repeating units enclosed in parentheses with the symbols a1, b1, c1, and d1 may be present in any order.] The fluorosilicone compound according to any one of the above [1] to [4], wherein the fluorosilicone compound is a group represented by the following formula: [6] X is -(Ar) a1 -(O) d1 -(CH2) c1 - [In formula: Ar is a fluorine atom or R A is an optionally substituted divalent aromatic group, preferably an unsubstituted divalent aromatic group, a1 is 0 or 1, c1 is an integer from 1 to 36, d1 is 0 or 1.] The fluorosilicone compound according to any one of the above [1] to [5], wherein the group is represented by the following formula: [7] The fluorosilicone compound according to any one of the above [1] to [6], wherein Y is an alkylene group or an alkyleneoxyalkylene group. [8] R Si is represented by the following formula (S1), (S2), (S3), (S4) or (S5): [ka] [In formula: R 11 are each independently a hydroxyl group or a hydrolyzable group, R 12 are each independently a monovalent organic group, n1 is (SiR 11 n1 R 12 3-n1 ) each unit independently represents an integer of 0 to 3, X 11 each independently represents a single bond or a divalent organic group, R 13 are each independently a hydrogen atom or a monovalent organic group, Each t is independently an integer of 2 or greater; R 14 each independently represents a hydrogen atom, a halogen atom, or -X 11 -SiR 11 n1 R 12 3-n1 and R 15 each independently represents a single bond, an oxygen atom, an alkylene group having 1 to 6 carbon atoms, or an alkyleneoxy group having 1 to 6 carbon atoms, R a1 are each independently -Z 1 -SiR 21 p1 R 22 q1 R 23 r1 and; Z 1 are each independently a divalent organic group, R 21 are each independently -Z 1’ -SiR 21’ p1’ R 22’ q1’ R 23’ r1’ and; R 22 are each independently a hydroxyl group or a hydrolyzable group, R 23 are each independently a monovalent organic group, p1 is independently an integer of 0 to 3, Each q1 is independently an integer of 0 to 3, Each r1 is independently an integer of 0 to 3, Z1’ are each independently a divalent organic group, R 21’ are each independently -Z 1” -SiR 22” q1” R 23” r1” and; R 22’ are each independently a hydroxyl group or a hydrolyzable group, R 23’ are each independently a monovalent organic group, p1' is independently an integer of 0 to 3, Each q1' is independently an integer of 0 to 3, Each r1' is independently an integer of 0 to 3, Z 1” are each independently a divalent organic group, R 22” are each independently a hydroxyl group or a hydrolyzable group, R 23” are each independently a monovalent organic group, Each q1" is independently an integer of 0 to 3, Each r1" is independently an integer of 0 to 3, R b1 are each independently a hydroxyl group or a hydrolyzable group, R c1 are each independently a monovalent organic group, Each k1 is independently an integer of 0 to 3, Each l1 is independently an integer of 0 to 3; Each m1 is independently an integer of 0 to 3, R d1 are each independently -Z 2 -CR 31 p2 R 32 q2 R 33 r2 and Z 2 each independently represents a single bond, an oxygen atom, or a divalent organic group, R 31 are each independently -Z 2’ -CR 32’ q2’ R 33’ r2’ and R 32 are each independently -Z 3 -SiR 34 n2 R 35 3-n2 and R 33 each independently represents a hydrogen atom, a hydroxyl group, or a monovalent organic group, p2 is independently an integer of 0 to 3, Each q2 is independently an integer of 0 to 3, Each r2 is independently an integer of 0 to 3; Z 2’ each independently represents a single bond, an oxygen atom, or a divalent organic group, R 32’ are each independently -Z 3 -SiR 34 n2 R 35 3-n2 and R 33’ each independently represents a hydrogen atom, a hydroxyl group, or a monovalent organic group, Each q2' is independently an integer of 0 to 3, Each r2' is independently an integer of 0 to 3, Z 3 each independently represents a single bond, an oxygen atom, or a divalent organic group; R 34 are each independently a hydroxyl group or a hydrolyzable group, R 35 are each independently a monovalent organic group, Each n2 is independently an integer of 0 to 3, R e1 are each independently -Z 3 -SiR 34 n2 R 353-n2 and R f1 each independently represents a hydrogen atom, a hydroxyl group, or a monovalent organic group, Each k2 is independently an integer of 0 to 3, Each l2 is independently an integer of 0 to 3; Each m2 is independently an integer of 0 to 3. R g1 and R h1 are each independently -Z 4 -SiR 11 n1 R 12 3-n1 , -Z 4 -SiR a1 k1 R b1 l1 R c1 m1 , or -Z 4 -CR d1 k2 R e1 l2 R f1 m2 and Z 4 each independently represents a single bond, an oxygen atom, or a divalent organic group, 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 fluorosilicone compound according to any one of the above [1] to [7], wherein the fluorosilicone compound is a group represented by the following formula: [9] A release composition comprising the fluorosilicone compound according to any one of the above items [1] to [8].

[10] The release composition according to the above [9], further comprising a liquid medium which is at least one selected from water and an organic solvent.

[11] The release composition according to the above [9] or

[10] , which is a solution or aerosol containing an organic solvent, or an aqueous emulsion containing water.

[12] The release composition according to any one of the above items [9] to

[11] , further comprising a curing-accelerating catalyst in an amount of 0.05 parts by weight to 10 parts by weight based on 100 parts by weight of the fluorosilicone compound (I).

[13] The release composition according to any one of the above items [9] to

[12] , further comprising at least one selected from the group consisting of silicone oil, silicone resin, synthetic wax, natural wax, fluorinated oil and fluorinated resin in an amount of 0.1 parts by weight to 99 parts by weight based on 100 parts by weight of the fluorosilicone compound (I).

[14] A coating obtained from the release composition according to any one of the above items [9] to

[13] .

[15] (i) A step of applying the release composition according to any one of the above items [9] to

[13] to the inner surface of a molding die to form a coating of the release composition. A method for forming a release agent coating comprising the steps of:

[16] (i) a step of applying the mold release composition according to any one of the above items [9] to

[13] to the inner surface of a molding die to form a coating of the mold release composition; (ii) filling a mold having a coating of the release composition with a molding composition to obtain a molded body; and (iii) Step of removing the molded body from the mold A method for producing a molded body, comprising the steps of: Effect of the Invention

[0006] The fluorosilicone compound of the present disclosure can provide excellent releasability. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0007] As used herein, the term "monovalent organic group" refers to a monovalent group containing carbon. The monovalent organic group is not particularly limited, but may be a hydrocarbon group or a derivative thereof. A derivative of a hydrocarbon group refers to a group having one or more N, O, S, Si, amide, sulfonyl, siloxane, carbonyl, carbonyloxy, etc. at the end of the hydrocarbon group or in the molecular chain.

[0008] As used herein, the term "divalent organic group" is not particularly limited, but includes divalent groups in which one hydrogen atom has been further eliminated from a hydrocarbon group.

[0009] As used herein, the term "hydrocarbon group" refers to a group containing carbon and hydrogen, with one hydrogen atom removed from the molecule. Such a hydrocarbon group is not particularly limited, but may be a hydrocarbon group having 1 to 20 carbon atoms, such as an aliphatic hydrocarbon group, an aromatic hydrocarbon group, etc. The above-mentioned "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. Such a 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 in the molecular chain.

[0010] As used herein, examples of the substituents of the "hydrocarbon group" include, but are not limited to, halogen atoms; 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 of the alkyl group include one or more groups selected from an aryl group and a 5- to 10-membered heteroaryl group.

[0011] As used herein, the term "hydrolyzable group" refers to a group that can undergo hydrolysis, i.e., a group that can be removed from the main skeleton of a compound by hydrolysis. Examples of hydrolyzable groups include -OR h , -OCOR h , -ON=CR h 2, -NRh 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, and methyl or ethyl groups are more preferred. In one embodiment, R h is a methyl group, and in another embodiment, R h is an ethyl group.

[0012] The fluorosilicone compounds of the present disclosure have the formula (I): [ka] [In formula: R A 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-, R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group; R 3 and R 10each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, R A -X-, or R Si -Y-, X and Y are each independently a divalent organic group; R Si is a monovalent group containing a Si atom having a hydroxyl group or a hydrolyzable group bonded thereto, m is an integer from 1 to 100; n is an integer from 1 to 50; o is an integer from 0 to 200; The repeating units enclosed in parentheses with m, n, and o may occur in any order.] It is expressed as:

[0013] R A 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-. R A may be preferably 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-.

[0014] In one embodiment, R A can be CF3O-.

[0015] In another embodiment, R A can be CF3NH- or (CF3)2N-, preferably CF3NH-.

[0016] R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0017] Substituents for the alkyl and aryl groups include halogen atoms; 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 of the halogen atom include one or more groups selected from an aryl group and a 5- to 10-membered heteroaryl group. The halogen atom is a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and preferably a chlorine atom.

[0018] In one embodiment, the alkyl group may be an alkyl group that may be substituted with a halogen atom, such as a chlorine atom.

[0019] In one embodiment, the aryl group is a halogen atom, such as a chlorine atom, or a C-C alkyl group, such as a methyl group. 10 It may be an aryl group which may be substituted with an alkyl group of the formula:

[0020] The alkyl group is preferably C 1-20 Alkyl groups, more preferably C 1-12 Alkyl groups, more preferably C 1-4 It may be an alkyl group, and even more preferably a methyl group.

[0021] The aryl group is preferably C 6-20 Aryl groups, more preferably C 6-12It may be an aryl group, more preferably a phenyl group.

[0022] In one embodiment, R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 may each independently be an unsubstituted alkyl group such as a methyl group, an ethyl group, a propyl group, a hexyl group, or a dodecyl group; a substituted alkyl group such as a chloromethyl group, an unsubstituted aryl group such as a phenyl group or a naphthyl group; or a substituted aryl group such as a 4-chlorophenyl group or a 2-methylphenyl group. Among these, an alkyl group, particularly an unsubstituted alkyl group, is preferred, and a methyl group is more preferred.

[0023] R 3 and R 10 each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, R A -X-, or R Si -Y-.

[0024] R 3 and R 10 The substituted or unsubstituted alkyl group and the substituted or unsubstituted aryl group in 1 This has the same meaning as described above with respect to the above.

[0025] In one embodiment, R 3 and R 10 are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

[0026] In another embodiment, R A -X-, or R Si -Y-.

[0027] Each X is independently a divalent organic group.

[0028] In one embodiment, X is -(Ar) a1 -(CFH) b1 -(CH2) c1 -(O) d1 - [In formula: Ar is a fluorine atom or R A is a divalent aromatic group optionally substituted by R A 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-, a1 is an integer from 0 to 10, b1 is an integer from 0 to 200, c1 is an integer from 0 to 200, d1 is an integer from 0 to 10, The repeating units enclosed in parentheses with the symbols a1, b1, c1, and d1 may be present in any order.] In the formula, however, it is preferable that oxygen atoms are not consecutive. In other words, it is preferable that there is no -OO- bond. In addition, when the left side of X is R A Bind to.

[0029] The aromatic group includes aromatic rings containing only carbon as ring atoms (so-called arylenes), as well as aromatic rings further containing nitrogen, oxygen or sulfur (so-called heteroarylenes), and groups having multiple aromatic rings.

[0030] The aromatic group preferably has a benzene ring, a naphthalene ring, a phenanthrene ring, an anthracene ring, a tetracene ring, a pentacene ring, a benzopyrene ring, a chrysene ring, a pyrene ring, a triphenylene ring, a corannulene ring, an ovalene ring, an indole ring, a furan ring, a thiophene ring, a pyrrole ring, a pyrazole ring, an imidazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a biphenyl ring, a terphenyl ring, a triphenylmethane ring, or a benzophenone ring.

[0031] In one embodiment, the aromatic group preferably has a benzene ring, a naphthalene ring, a phenanthrene ring, an anthracene ring, a tetracene ring, a pentacene ring, a benzopyrene ring, a chrysene ring, a pyrene ring, a triphenylene ring, a corannulene ring, or an ovalene ring, more preferably a benzene ring or a naphthalene ring, and even more preferably a benzene ring.

[0032] In another embodiment, the aromatic group preferably has an indole ring, a furan ring, a thiophene ring, a pyrrole ring, a pyrazole ring, an imidazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring, more preferably an indole ring.

[0033] In another embodiment, the aromatic group preferably has a biphenyl ring, a terphenyl ring, a triphenylmethane ring, or a benzophenone ring.

[0034] In one embodiment, Ar is an unsubstituted divalent aromatic group.

[0035] In another embodiment, Ar is a fluorine atom or R A is a divalent aromatic group substituted by

[0036] In another embodiment, Ar is R A is a divalent aromatic group substituted by

[0037] In another embodiment, Ar is a divalent aromatic group substituted with a fluorine atom.

[0038] The number of the substituents of the aromatic group is not particularly limited, and may be, for example, 1 to 10, 1 to 5, 1 to 3, 1, 2, or 3. In one embodiment, the number of the substituents of the aromatic group is 1 or more. In another embodiment, the aromatic group is fully substituted.

[0039] a1 is an integer of 0 to 10, preferably 0 or 1.

[0040] In one embodiment, a1 is 0.

[0041] In another embodiment, a1 is 1.

[0042] b1 is an integer of 0 to 200, preferably an integer of 0 to 6.

[0043] c1 is an integer of 0 to 200, preferably an integer of 0 to 30.

[0044] d1 is an integer of 0 to 10, and preferably an integer of 0 to 3.

[0045] In one embodiment, X is -(Ar) a1 -(O) d1 -(CH2) c1 - [In formula: Ar is a fluorine atom or R A is an optionally substituted divalent aromatic group, preferably an unsubstituted divalent aromatic group, a1 is 0 or 1, c1 is an integer from 1 to 36, preferably an integer from 1 to 30, and may be, for example, an integer from 1 to 9, an integer from 1 to 3, or an integer from 2 to 3; d1 is 0 or 1.] It is a group represented by the following formula:

[0046] In one embodiment, X is -(CH2) c1 - [In the formula, c1 is an integer of 1 to 36, preferably an integer of 1 to 30, and can be, for example, an integer of 1 to 9, or an integer of 1 to 3.] It is a group represented by the following formula:

[0047] In one embodiment, X is -Ar-O-(CH2) c1 - [In formula: Ar is a fluorine atom or R A is an optionally substituted divalent aromatic group, preferably an unsubstituted divalent aromatic group, c1 is an integer from 1 to 36, preferably an integer from 1 to 30, and can be, for example, an integer from 1 to 9, an integer from 1 to 3, or an integer from 2 to 3.] It is a group represented by the following formula:

[0048] Each Y is independently a divalent organic group.

[0049] Y may be a divalent organic group preferably having 1 to 20 carbon atoms, more preferably having 1 to 12 carbon atoms.

[0050] Y is preferably an alkylene group (preferably having 1 to 20 carbon atoms, more preferably having 1 to 12 carbon atoms), such as an ethylene group, a propylene group, a methylethylene group, an octylene group, and a decylene group, and an alkyleneoxyalkylene group (preferably having 2 to 20 carbon atoms, more preferably having 2 to 12 carbon atoms), such as an ethyleneoxymethylene group, a propyleneoxymethylene group, a propyleneoxyethylene group, and an ethyleneoxybutylene group. Y is more preferably -(CH2) r wherein r is an integer of 2 to 200, preferably an integer of 2 to 12.

[0051] R Si is a monovalent group containing a silicon atom having a hydroxyl group or a hydrolyzable group bonded thereto.

[0052] R Si is preferably a group represented by formula (S1), (S2), (S3), (S4) or (S5). [ka]

[0053] R 11 are each independently a hydroxyl group or a hydrolyzable group.

[0054] R 11 are preferably each independently a hydrolyzable group.

[0055] R 12 are each independently a monovalent organic group. 12 does not contain a hydrolyzable group.

[0056] R 12 In the above, the monovalent organic group is preferably C 1-20 is an alkyl group, more preferably C 1-6 It is preferably an alkyl group, more preferably a methyl group.

[0057] 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.

[0058] n1 is (SiR 11 n1 R 12 3-n1 ) units are each independently preferably an integer of 1 to 3, more preferably 2 or 3, and even more preferably 3.

[0059] In the above formula, X 11 are each independently a single bond or a divalent organic group. Such a divalent organic group is preferably -R 28-O x -R 29 -(In the formula, R 28 and R 29 each independently represents a single bond or C 1-20 is an alkylene group, and x is 0 or 1. 1-20 The alkylene group may be linear or branched, but is preferably linear. 1-20 The alkylene group is preferably 1-10 Alkylene group, more preferably C 1-6 Alkylene group, more preferably C 1-3 It is an alkylene group.

[0060] In one embodiment, X 11 are each independently -C 1-6 Alkylene-OC 1-6 Alkylene- or -OC 1-6 It is alkylene.

[0061] In a preferred embodiment, X 11 are each independently a single bond or a linear C 1-6 An alkylene group, preferably a single bond or a straight chain C 1-3 Alkylene group, more preferably a single bond or a straight chain C 1-2 It is preferably a linear C 1-2 It is an alkylene group.

[0062] R 13 are each independently a hydrogen atom or a monovalent organic group. Such a monovalent organic group is preferably 1-20 It is an alkyl group.

[0063] In a preferred embodiment, R 13 are each independently a hydrogen atom or a straight-chain C 1-6 is an alkyl group, preferably a hydrogen atom or a straight-chain C 1-3 It is an alkyl group, preferably a hydrogen atom or a methyl group.

[0064] R 15 are each independently a single bond, an oxygen atom, or C1-6 Alkylene group or C 1-6 It is an alkyleneoxy group.

[0065] 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.

[0066] In a preferred embodiment, R 15 is a single bond.

[0067] Each t is independently an integer of 2 or greater.

[0068] In a preferred embodiment, each t is independently an integer of 2 to 10, preferably an integer of 2 to 6.

[0069] R 14 each independently represents a hydrogen atom, a halogen atom, or -X 11 -SiR 11 n1 R 12 3-n1 The halogen atom is preferably an iodine atom, a chlorine atom or a fluorine atom, more preferably a fluorine atom. In a preferred embodiment, R 14 is a hydrogen atom.

[0070] In one embodiment, formula (S1) is formula (S1-a) below. [ka] [In the formula, R 11 , R 12 , R 13 , X 11 and n1 are as defined in formula (S1) above. t1 and t2 each independently represent an integer of 1 or more, preferably an integer of 1 to 10, more preferably an integer of 2 to 10, for example, an integer of 1 to 5 or an integer of 2 to 5; The order of occurrence of each repeating unit enclosed in parentheses with t1 and t2 is arbitrary in the formula.

[0071] In a preferred embodiment, formula (S1) is formula (S1-b) below. [ka] [In the formula, R 11 , R 12 , R 13 , X 11 , n1 and t are as defined above in formula (S1).

[0072] In a preferred embodiment, in formula (S2), -SiR 11 n1 R 12 3-n1 The Si atom does not form a siloxane bond.

[0073] In one embodiment, in formula (S2), there are at least two Si atoms having hydroxyl or hydrolyzable groups bonded thereto.

[0074] R a1 are each independently -Z 1 -SiR 21 p1 R 22 q1 R 23 r1 It is.

[0075] Above Z 1 are each independently an oxygen atom or a divalent organic group. 1 The structure written as is shown on the right side (SiR 21 p1 R 22 q1 R 23 r1 )

[0076] In a preferred embodiment, Z 1 is a divalent organic group.

[0077] In a preferred embodiment, Z1 is Z 1 Preferably, in formula (S3), (Si-Z) does not include a compound that forms a siloxane bond with the Si atom to which it is bonded. 1 --Si) does not contain a siloxane bond.

[0078] Above Z 1 is preferably C 1-6 Alkylene group, -(CH2) z1 -O-(CH2) z2 - (wherein z1 is an integer of 0 to 6, for example, an integer of 1 to 6, and z2 is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z3 -Phenylene-(CH2) z4 - (wherein z3 is an integer of 0 to 6, for example, an integer of 1 to 6, and z4 is an integer of 0 to 6, for example, an integer of 1 to 6). 1-6 The alkylene groups may be linear or branched, but are preferably linear. These groups may contain, for example, fluorine atoms, C 1-6 Alkyl group, C 2-6 Alkenyl groups, and C 2-6 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.

[0079] In a preferred embodiment, Z 1 is C 1-6 Alkylene group or -(CH2) z3 -Phenylene-(CH2) z4 -, preferably -phenylene-(CH2) z4 -It is.

[0080] 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-.

[0081] R 21 are each independently -Z 1’-SiR 21’ p1’ R 22’ q1’ R 23’ r1’ It is.

[0082] Above Z 1’ are each independently an oxygen atom or a divalent organic group. 1’ The structure written as is shown on the right side (SiR 21’ p1’ R 22’ q1’ R 23’ r1’ )

[0083] In a preferred embodiment, Z 1’ is a divalent organic group.

[0084] In a preferred embodiment, Z 1’ is Z 1’ Preferably, in formula (S3), (Si-Z) does not include a compound that forms a siloxane bond with the Si atom to which it is bonded. 1’ --Si) does not contain a siloxane bond.

[0085] Above Z 1’ is preferably C 1-6 Alkylene group, -(CH2) z1’ -O-(CH2) z2’ - (wherein z1' is an integer of 0 to 6, for example, an integer of 1 to 6, and z2' is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z3’ -Phenylene-(CH2) z4’ - (wherein z3' is an integer of 0 to 6, for example, an integer of 1 to 6, and z4' is an integer of 0 to 6, for example, an integer of 1 to 6). 1-6 The alkylene groups may be linear or branched, but are preferably linear. These groups may contain, for example, fluorine atoms, C 1-6 Alkyl group, C 2-6 Alkenyl groups, and C 2-6 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.

[0086] In a preferred embodiment, Z 1’ is C 1-6 Alkylene group or -(CH2) z3’ -Phenylene-(CH2) z4’ -, preferably -phenylene-(CH2) z4’ -It is.

[0087] 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-.

[0088] R 21’ are each independently -Z 1” -SiR 22” q1” R 23” r1” It is.

[0089] Z 1” are each independently an oxygen atom or a divalent organic group. 1” The structure written as is shown on the right side (SiR 22” q1” R 23” r1” )

[0090] In a preferred embodiment, Z 1” is a divalent organic group.

[0091] In a preferred embodiment, Z 1” is Z 1” Preferably, in formula (S3), (Si-Z) does not include a compound that forms a siloxane bond with the Si atom to which it is bonded. 1” --Si) does not contain a siloxane bond.

[0092] Z 1” is preferably C 1-6 Alkylene group, -(CH2) z1”-O-(CH2) z2” - (wherein z1" is an integer of 0 to 6, for example, an integer of 1 to 6, and z2" is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z3” -Phenylene-(CH2) z4” - (wherein z3" is an integer of 0 to 6, for example, an integer of 1 to 6, and z4" is an integer of 0 to 6, for example, an integer of 1 to 6). 1-6 The alkylene groups may be linear or branched, but are preferably linear. These groups may contain, for example, fluorine atoms, C 1-6 Alkyl group, C 2-6 Alkenyl groups, and C 2-6 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.

[0093] In a preferred embodiment, Z 1” is C 1-6 Alkylene group or -(CH2) z3” -Phenylene-(CH2) z4” -, preferably -phenylene-(CH2) z4” -It is. 1” is such a group, light resistance, particularly ultraviolet resistance, can be improved.

[0094] 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-.

[0095] R 22” are each independently a hydroxyl group or a hydrolyzable group.

[0096] R 22” are preferably each independently a hydrolyzable group.

[0097] R 23”are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.

[0098] R 23” In the above, the monovalent organic group is preferably C 1-20 is an alkyl group, more preferably C 1-6 It is preferably an alkyl group, more preferably a methyl group.

[0099] 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.

[0100] q1” is (SiR 22” q1” R 23” r1” ) units are each independently preferably an integer of 1 to 3, more preferably 2 or 3, and even more preferably 3.

[0101] R 22’ are each independently a hydroxyl group or a hydrolyzable group.

[0102] R 22’ are preferably each independently a hydrolyzable group.

[0103] R 23’ are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.

[0104] R 23’ In the above, the monovalent organic group is preferably C 1-20 is an alkyl group, more preferably C 1-6 It is preferably an alkyl group, more preferably a methyl group.

[0105] Each of the p1's is independently an integer of 0 to 3, each of the q1's is independently an integer of 0 to 3, and each of the r1's is independently an integer of 0 to 3. The sum of p', q1', and r1' is (SiR 21’ p1’ R 22’ q1’ R 23’ r1’ ) units, it is 3.

[0106] In one embodiment, p1' is 0.

[0107] 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.

[0108] In one embodiment, q1' is (SiR 21’ p1’ R 22’ q1’ R 23’ r1’ ) units each independently represents an integer of 1 to 3, preferably an integer of 2 or 3, and more preferably 3.

[0109] In one embodiment, p1' is 0 and q1' is (SiR 21’ p1’ R 22’ q1’ R 23’ r1’ ) units each independently represents an integer of 1 to 3, preferably an integer of 2 or 3, and more preferably 3.

[0110] R 22 are each independently a hydroxyl group or a hydrolyzable group.

[0111] R 22 are preferably each independently a hydrolyzable group.

[0112] R 23 are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.

[0113] R 23 In the above, the monovalent organic group is preferably C 1-20 is an alkyl group, more preferably C 1-6 It is preferably an alkyl group, more preferably a methyl group.

[0114] 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.

[0115] In one embodiment, p1 is 0.

[0116] 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.

[0117] In one embodiment, q1 is (SiR 21 p1 R 22 q1 R 23 r1 ) units each independently represents an integer of 1 to 3, preferably an integer of 2 or 3, and more preferably 3.

[0118] In one embodiment, p1 is 0 and q1 is (SiR 21 p1 R 22 q1R 23 r1 ) units each independently represents an integer of 1 to 3, preferably an integer of 2 or 3, and more preferably 3.

[0119] R b1 are each independently a hydroxyl group or a hydrolyzable group.

[0120] R b1 are preferably each independently a hydrolyzable group.

[0121] R c1 are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.

[0122] R c1 In the above, the monovalent organic group is preferably C 1-20 is an alkyl group, more preferably C 1-6 It is preferably an alkyl group, more preferably a methyl group.

[0123] 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.

[0124] In one embodiment, k1 is (SiR a1 k1 R b1 l1 R c1 m1 ) units are each independently an integer of 1 to 3, preferably 2 or 3, and more preferably 3. In a preferred embodiment, k1 is 3.

[0125] In formula (S3), there are at least two Si atoms having hydroxyl groups or hydrolyzable groups bonded thereto.

[0126] In a preferred embodiment, there are at least two Si atoms to which hydroxyl groups or hydrolyzable groups are bonded in the terminal portion of formula (S3).

[0127] 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.

[0128] In a preferred embodiment, in formula (S3), R 21’ When present, at least one, and preferably all, R 21’ In the above formula, q1″ is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.

[0129] In a preferred embodiment, in formula (S3), R 21 When present, at least one, and preferably all, R 21In the above formula, p1' is 0, and q1' is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.

[0130] In a preferred embodiment, in formula (S3), R a1 When present, at least one, and preferably all, R a1 In the above formula, p1 is 0, and q1 is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.

[0131] 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.

[0132] R d1 are each independently -Z 2 -CR 31 p2 R 32 q2 R 33 r2 It is.

[0133] Z 2 are each independently a single bond, an oxygen atom, or a divalent organic group. 2 The structure written as is shown on the right side (CR 31 p2 R 32 q2 R 33 r2 )

[0134] In a preferred embodiment, Z 2 is a divalent organic group.

[0135] In a preferred embodiment, Z 2 does not contain a siloxane bond.

[0136] Z 2 is preferably C 1-6 Alkylene group, -(CH2) z5 -O-(CH2) z6- (wherein z5 is an integer of 0 to 6, for example, an integer of 1 to 6, and z6 is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z7 -Phenylene-(CH2) z8 - (wherein z7 is an integer of 0 to 6, for example, an integer of 1 to 6, and z8 is an integer of 0 to 6, for example, an integer of 1 to 6). 1-6 The alkylene groups may be linear or branched, but are preferably linear. These groups may contain, for example, fluorine atoms, C 1-6 Alkyl group, C 2-6 Alkenyl groups, and C 2-6 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.

[0137] In a preferred embodiment, Z 2 is C 1-6 Alkylene group or -(CH2) z7 -Phenylene-(CH2) z8 -, preferably -phenylene-(CH2) z8 -It is. 2 is such a group, light resistance, particularly ultraviolet resistance, can be improved.

[0138] 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-.

[0139] R 31 are each independently -Z 2’ -CR 32’ q2’ R 33’ r2’ It is.

[0140] Z 2’ are each independently a single bond, an oxygen atom, or a divalent organic group. 2’ The structure written as is shown on the right side (CR 32’q2’ R 33’ r2’ )

[0141] In a preferred embodiment, Z 2’ does not contain a siloxane bond.

[0142] Z 2’ is preferably C 1-6 Alkylene group, -(CH2) z5’ -O-(CH2) z6’ - (wherein z5' is an integer of 0 to 6, for example, an integer of 1 to 6, and z6' is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z7’ -Phenylene-(CH2) z8’ - (wherein z7' is an integer of 0 to 6, for example, an integer of 1 to 6, and z8' is an integer of 0 to 6, for example, an integer of 1 to 6). 1-6 The alkylene groups may be linear or branched, but are preferably linear. These groups may contain, for example, fluorine atoms, C 1-6 Alkyl group, C 2-6 Alkenyl groups, and C 2-6 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.

[0143] In a preferred embodiment, Z 2’ is C 1-6 Alkylene group or -(CH2) z7’ -Phenylene-(CH2) z8’ -, preferably -phenylene-(CH2) z8’ -It is. 2’ is such a group, light resistance, particularly ultraviolet resistance, can be improved.

[0144] 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-.

[0145] R 32’ are each independently -Z 3 -SiR 34 n2 R 35 3-n2 It is.

[0146] Z 3 are each independently a single bond, an oxygen atom, or a divalent organic group. 3 The structure written as is shown on the right side (SiR 34 n2 R 35 3-n2 )

[0147] In one embodiment, Z 3 is an oxygen atom.

[0148] In one embodiment, Z 3 is a divalent organic group.

[0149] In a preferred embodiment, Z 3 does not contain a siloxane bond.

[0150] Z 3 is preferably C 1-6 Alkylene group, -(CH2) z5” -O-(CH2) z6” - (wherein z5" is an integer of 0 to 6, for example, an integer of 1 to 6, and z6" is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z7” -Phenylene-(CH2) z8” - (wherein z7" is an integer of 0 to 6, for example, an integer of 1 to 6, and z8" is an integer of 0 to 6, for example, an integer of 1 to 6). 1-6 The alkylene groups may be linear or branched, but are preferably linear. These groups may contain, for example, fluorine atoms, C 1-6 Alkyl group, C 2-6 Alkenyl groups, and C 2-6 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.

[0151] In a preferred embodiment, Z 3 is C 1-6 Alkylene group or -(CH2) z7” -Phenylene-(CH2) z8” -, preferably -phenylene-(CH2) z8” -It is. 3 is such a group, light resistance, particularly ultraviolet resistance, can be improved.

[0152] 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-.

[0153] R 34 are each independently a hydroxyl group or a hydrolyzable group.

[0154] R 34 are preferably each independently a hydrolyzable group.

[0155] R 35 are each independently a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.

[0156] R 35 In the above, the monovalent organic group is preferably C 1-20 is an alkyl group, more preferably C 1-6 It is preferably an alkyl group, more preferably a methyl group.

[0157] 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 353-n2 In other words, at least two Si atoms having hydroxyl groups or hydrolyzable groups bonded thereto are present in the terminal portion of formula (S4).

[0158] n2 is (SiR 34 n2 R 35 3-n2 ) units are each independently preferably an integer of 1 to 3, more preferably 2 or 3, and even more preferably 3.

[0159] Above R 33’ are each independently a hydrogen atom, a hydroxyl group, or a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.

[0160] Above R 33’ In the above, the monovalent organic group is preferably C 1-20 Alkyl group or -(C s H 2s ) t1 -(OC s H 2s ) t2 (wherein s is an integer of 1 to 6, preferably an integer of 2 to 4; t1 is 1 or 0, preferably 0; and t2 is an integer of 1 to 20, preferably an integer of 2 to 10, more preferably an integer of 2 to 6), more preferably C 1-20 Alkyl groups, more preferably C 1-6 An alkyl group, particularly preferably a methyl group, is preferred.

[0161] In one embodiment, R 33’ is a hydroxyl group.

[0162] In another embodiment, R 33’ is a monovalent organic group, preferably C 1-20 is an alkyl group, more preferably C 1-6 It is an alkyl group.

[0163] Each of the q2's is independently an integer of 0 to 3, and each of the r2's is independently an integer of 0 to 3. The sum of q2' and r2' is not more than (CR 32’ q2’ R 33’ r2’ ) units, it is 3.

[0164] q2' is (CR 32’ q2’ R 33’ r2’ ) units are each independently preferably an integer of 1 to 3, more preferably 2 or 3, and even more preferably 3.

[0165] R 32 are each independently -Z 3 -SiR 34 n2 R 35 3-n2 This is -Z 3 -SiR 34 n2 R 35 3-n2 is the above R 32’ This has the same meaning as described above.

[0166] R 33 are each independently a hydrogen atom, a hydroxyl group, or a monovalent organic group. Such monovalent organic groups are monovalent organic groups excluding the above hydrolyzable groups.

[0167] R 33 In the above, the monovalent organic group is preferably C 1-20 Alkyl group or -(C s H 2s ) t1 -(OC s H 2s ) t2 -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), more preferably C 1-20 Alkyl groups, more preferably C 1-6An alkyl group, particularly preferably a methyl group, is preferred.

[0168] In one embodiment, R 33 is a hydroxyl group.

[0169] In another embodiment, R 33 is a monovalent organic group, preferably C 1-20 is an alkyl group, more preferably C 1-6 It is an alkyl group.

[0170] 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.

[0171] In one embodiment, p2 is 0.

[0172] 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.

[0173] In one embodiment, q2 is (CR 31 p2 R 32 q2 R 33 r2 ) units each independently represents an integer of 1 to 3, preferably an integer of 2 or 3, and more preferably 3.

[0174] In one embodiment, p2 is 0 and q2 is (CR 31 p2 R 32 q2 R33 r2 ) units each independently represents an integer of 1 to 3, preferably an integer of 2 or 3, and more preferably 3.

[0175] Above R e1 are each independently -Z 3 -SiR 34 n2 R 35 3-n2 This is -Z 3 -SiR 34 n2 R 35 3-n2 is the above R 32’ This has the same meaning as described above.

[0176] 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 hydrolyzable groups.

[0177] Above R f1 In the above, the monovalent organic group is preferably C 1-20 Alkyl group or -(C s H 2s ) t1 -(OC s H 2s ) t2 -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), more preferably C 1-20 Alkyl groups, more preferably C 1-6 An alkyl group, particularly preferably a methyl group, is preferred.

[0178] In one embodiment, R f1 is a hydroxyl group.

[0179] In another embodiment, R f1 is a monovalent organic group, preferably C 1-20 is an alkyl group, more preferably C 1-6 It is an alkyl group.

[0180] The above k2's are each independently an integer of 0 to 3, the l2's are each independently an integer of 0 to 3, and the m2's are each independently an integer of 0 to 3. The sum of k2, l2, and m2 is (CR d1 k2 R e1 l2 R f1 m2 ) units, it is 3.

[0181] 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 2 or more, for example, 2 to 27, preferably 2 to 9, more preferably 2 to 6, further preferably 2 to 3, and particularly preferably 3.

[0182] In a preferred embodiment, in formula (S4), R 32’ When present, at least one, and preferably all, R 32’ In the above formula, n2 is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.

[0183] In a preferred embodiment, in formula (S4), R 32 When present, at least one, and preferably all, R 32 In the above formula, n2 is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.

[0184] In a preferred embodiment, in formula (S4), R e1 When present, at least one, and preferably all, R a1 In the above formula, n2 is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.

[0185] 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.

[0186] 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 are as defined above.

[0187] In a preferred embodiment, R g1 and R h1 are each independently -Z 4 -SiR 11 n1 R 12 3-n1 It is.

[0188] Above Z 4 are each independently a single bond, an oxygen atom, or a divalent organic group. 4 The structure written as is shown on the right side (SiR 11 n1 R 12 3-n1 )

[0189] In one embodiment, Z 4 is an oxygen atom.

[0190] In one embodiment, Z 4 is a divalent organic group.

[0191] In a preferred embodiment, Z 4 does not contain a siloxane bond.

[0192] Above Z 4 is preferably C 1-6 Alkylene group, -(CH2) z5” -O-(CH2) z6” - (wherein z5" is an integer of 0 to 6, for example, an integer of 1 to 6, and z6" is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z7” -Phenylene-(CH2) z8” - (wherein z7" is an integer of 0 to 6, for example, an integer of 1 to 6, and z8" is an integer of 0 to 6, for example, an integer of 1 to 6). 1-6 The alkylene groups may be linear or branched, but are preferably linear. These groups may contain, for example, fluorine atoms, C 1-6 Alkyl group, C 2-6 Alkenyl groups, and C 2-6 It may be substituted by one or more substituents selected from alkynyl groups, but is preferably unsubstituted.

[0193] In a preferred embodiment, Z 4 is C 1-6 Alkylene group or -(CH2) z7” -Phenylene-(CH2) z8” -, preferably -phenylene-(CH2) z8” -It is. 4 is such a group, light resistance, particularly ultraviolet resistance, can be improved.

[0194] 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 4can be -CH2CH2-.

[0195] In a preferred embodiment, formulas (S1), (S2), (S3), (S4) and (S5) do not contain a siloxane bond.

[0196] In one embodiment, R Si is a group represented by formula (S3), (S4) or (S5).

[0197] In one embodiment, R Si is a group represented by formula (S3) or (S4).

[0198] In one embodiment, R Si is a group represented by formula (S4) or (S5).

[0199] In one embodiment, R Si is a group represented by formula (S1). In a preferred embodiment, formula (S1) is a group represented by formula (S1-b). In a preferred embodiment, 13 is a hydrogen atom, and X 11 is a single bond or -R 28 -O x -R 29 -(In the formula, R 28 and R 29 each independently represents a single bond or C 1-20 an alkylene group, and x is 0 or 1; and n1 is 1 to 3, preferably 2 to 3, and more preferably 3.

[0200] In one embodiment, R Si is a group represented by formula (S2). In a preferred embodiment, formula (S2) is -SiR 11 2R 12 , or -SiR 11 The answer is 3.

[0201] In one embodiment, R Si is a group represented by formula (S3). In a preferred embodiment, formula (S3) is -SiR a1 2R c1 , or -SiRa1 3, R a1 -Z 1 -SiR 22 q1 R 23 r1 and Z 1 is C 1-6 Alkylene group, -(CH2) z1 -O-(CH2) z2 - (wherein z1 is an integer of 0 to 6, for example, an integer of 1 to 6, and z2 is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z3 -Phenylene-(CH2) z4 - (wherein z3 is an integer of 0 to 6, for example, an integer of 1 to 6, and z4 is an integer of 0 to 6, for example, an integer of 1 to 6), preferably C 1-6 It is an alkylene group, and q1 is 1 to 3, preferably 2 to 3, and more preferably 3.

[0202] In one embodiment, R Si is a group represented by formula (S4). In a preferred embodiment, formula (S4) is -CR e1 2R f1 , or -CR e1 3, 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.

[0203] In one embodiment, R Siis a group represented by formula (S5). In a preferred embodiment, R g1 and R h1 -Z 4 -SiR 11 n1 R 12 3-n1 and Z 4 is C 1-6 Alkylene group, -(CH2) z5” -O-(CH2) z6” - (wherein z5" is an integer of 0 to 6, for example, an integer of 1 to 6, and z6" is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z7” -Phenylene-(CH2) z8” - (wherein z7" is an integer of 0 to 6, for example, an integer of 1 to 6, and z8" is an integer of 0 to 6, for example, an integer of 1 to 6), preferably C 1-6 It is an alkylene group, and n1 is 1 to 3, preferably 2 to 3, and more preferably 3.

[0204] m is an integer of 1 to 100, preferably an integer of 5 to 80, more preferably an integer of 10 to 50, for example, an integer of 20 to 50 or 20 to 40.

[0205] n is an integer of 1 to 50, preferably an integer of 1 to 20, more preferably an integer of 1 to 10, for example, an integer of 2 to 10.

[0206] o is an integer of 0 to 200, preferably an integer of 5 to 100, more preferably an integer of 10 to 80, and further preferably an integer of 15 to 50, for example, an integer of 20 to 50, 20 to 40, or 30 to 50.

[0207] The fluorosilicone compound represented by the above formula (I) is not particularly limited, but may be 1×10 2 ~1×10 6 The fluorosilicone compound represented by the above formula (I) may have a number average molecular weight of preferably 1000 to 100,000, and more preferably 2000 to 50,000. The "number average molecular weight" may be measured using GPC.

[0208] The fluorosilicone of formula (I) can be, for example, the following formula (II):

[0209] [ka] [In the formula, each symbol has the same meaning as defined in formula (I)] The Si-H containing compound represented by the formula: R A -X”-CH=CH2 or R Si -Y'-CH=CH2 [wherein X″ and Y′ are each a divalent group, preferably a divalent group having 1 to 18 carbon atoms, or a direct bond; R A and R Si has the same meaning as defined in formula (I) above. and a compound represented by the formula (I) in the presence of a hydrosilylation catalyst.

[0210] The present disclosure provides a mold release composition containing the fluorosilicone compound represented by formula (I) of the present disclosure, wherein the mold release composition can be only one product or a mixture of at least two products.

[0211] The fluorosilicone release composition of the present disclosure may contain a curing-accelerating catalyst. This catalyst is for accelerating the dehydration condensation reaction of silanol groups. Examples of the curing-accelerating catalyst are (preferably having 1-30 carbon atoms) organic metal salts, such as dibutyltin dilaurate, dibutyltin diacetate, tetrabutyl titanate (butoxytitanium), tetraisopropyl titanate (isopropoxytitanium), bis-(acetylacetonyl)-diisopropyl titanate, bis(ethylacetoacetate)diisopropyl titanate {bis(ethylacetoacetate)diisopropoxytitanium} and other chelates of titanium and zirconium disclosed in WO2001-49774 (the disclosure of which is incorporated herein), acids (particularly organic acids having 1-10 carbon atoms), such as acetic acid or propionic acid, and carboxylates.

[0212] The amount of the curing-accelerating catalyst added is usually at most 20 parts by weight, and preferably 0.05 to 10 parts by weight, based on 100 parts by weight of the fluorosilicone compound.

[0213] The fluorosilicone release composition of the present disclosure is preferably used in the form of a solution in a solvent such as an organic solvent. The solvent dissolves the fluorosilicone release composition and evaporates to deposit the fluorosilicone release agent. Examples of solvents include aliphatic solvents such as hexane, cyclohexane, heptane, octane, isooctane, industrial gasoline, aromatic solvents such as benzene, toluene and xylene, ester solvents such as ethyl acetate and butyl acetate, alcohol solvents such as isopropyl alcohol and ethanol, chlorine solvents such as trichloroethylene, chloroform and m-xylene hexachloride, ketone solvents such as acetone and methyl ethyl ketone, ether solvents such as diethyl ether, diisopropyl ether and tetrahydrofuran, fluorine solvents such as HCFC-225, HFC-365, methyl perfluorobutyl ether and ethyl perfluorobutyl ether, and silicone solvents with low boiling points (at most 150°C) such as hexamethyldisiloxane and heptamethyltrisiloxane.

[0214] The fluorosilicone mold release composition of the present disclosure may be in the form of an aerosol in which a solution of the fluorosilicone compound is filled with a propellant such as LPG.

[0215] The fluorosilicone mold release composition of the present disclosure may be a solution containing a fluorosilicone compound and an organic solvent, or an aqueous emulsion containing water.

[0216] When the release composition is an aqueous emulsion, it preferably contains at least one emulsifier selected from the group consisting of nonionic emulsifiers, anionic emulsifiers, and cationic emulsifiers.

[0217] The nonionic emulsifier may be any that can emulsify the fluoropolymer of the present disclosure and disperse it in an aqueous emulsion, and examples of the nonionic emulsifier include polyoxyethylene alkyl ethers, sorbitan alkylates, and sorbitan alkyl esters. Examples of the polyoxyethylene alkyl ethers include polyoxyethylene lauryl ether.

[0218] Examples of the anionic emulsifier include alkyl sulfates, alkyl sulfonates, and alkyl phosphates. Examples of the alkyl sulfates include sodium alkyl sulfate.

[0219] Examples of the cationic emulsifier include quaternary ammonium salts and alkylamine salts. Examples of the quaternary ammonium salts include lauryltrimethylammonium chloride.

[0220] The amount of the emulsifier is usually 0.5 to 25 parts by weight, preferably 1.0 to 20 parts by weight, more preferably 2.0 to 15 parts by weight, based on 100 parts by weight of the fluoropolymer.

[0221] The fluorosilicone release composition of the present disclosure can be applied by well-known methods. For example, the mold is immersed in a diluted solution of the release composition, sprayed with the diluted solution, or brushed with the diluted solution, and then the solvent is evaporated off. The mold is then heated to hydrolyze and condense with the silyl group moiety to form a cured film, thereby improving durability. Heating is preferably performed at 50 to 200°C for about 10 to 60 minutes.

[0222] The fluorosilicone release composition of the present disclosure can be used in a form mixed with other release components. Examples of other release components include natural waxes such as carnauba wax and beeswax; synthetic waxes such as Fischer-Tropsch wax, polyethylene wax and hydrogenated castor oil; various silicone oils and silicone resins; fluorine oils such as CTFE oil and PFPE oil; and fluorine resins such as PTFE and PCTFE. The amount of other release components can be 1 part by weight to 1000 parts by weight based on 100 parts by weight of the fluorosilicone compound (I).

[0223] When the release composition is an aerosol, it can be filled into an aerosol can using a propellant. Examples of the propellant include LPG, dimethyl ether, and carbon dioxide. The amount of the propellant is usually 10 to 95% by weight, preferably 20 to 90% by weight, and more preferably 30 to 90% by weight, based on the total amount of the release composition and the propellant. If the amount of the propellant is 10% by weight or more, the spraying can be performed better, and a more uniform coating tends to be obtained. If the amount of the propellant is 95% by weight or less, the coating does not become too thin, and the releasability tends not to decrease too much.

[0224] The release composition can be used as an internal or external release agent, preferably as an external release agent.

[0225] The release composition is usually used as follows: The release composition is applied to the inner surface of a molding die, and after the solvent and dispersant are dried and removed, a release agent coating (a fluoropolymer coating) is formed on the molding die, the molding composition is filled into the die to form a molding material, and the molding material is then removed from the die.

[0226] That is, the present disclosure further provides a method for forming the coating. For example, the method for forming the coating of the present disclosure includes the steps of: (i) applying the release composition of the present disclosure to the inner surface of a mold to form a coating of the release composition; Includes.

[0227] The present disclosure further provides a method for producing a molded article using the release composition of the present disclosure. For example, the method for producing a molded article of the present disclosure includes the steps of: (i) applying the release composition of the present disclosure to the inner surface of a mold to form a coating of the release composition; (ii) filling a mold having a coating of the release composition with a molding composition to obtain a molded body; and (iii) Step of removing the molded body from the mold Includes.

[0228] Examples of the mold for which the release composition can be used include metal molds such as aluminum, SUS, and iron, epoxy resin and wooden molds, and nickel electroformed or chrome plated molds.

[0229] Examples of molding materials that can be released using the release composition include rubbers such as urethane rubber, H-NBR, NBR, silicone rubber, EPDM, CR, NR, fluororubber, SBR, BR, IIR and IR, thermosetting resins such as urethane foam, epoxy resin, phenolic resin and FRP (e.g., CFRP and GFRP), and thermoplastic resins such as ABS, polycarbonate and PBT.

[0230] The present disclosure provides a coating obtained from a mold release composition containing a fluorosilicone compound represented by formula (I) of the present disclosure.

[0231] In the present disclosure, examples of raw materials for molded articles to be demolded include polyurethane, butyl rubber, styrene butadiene rubber, chloroprene rubber, EPDM, NBR, ACM, urethane rubber, silicone rubber, fluororubber, polycarbonate, epoxy resin, phenolic resin, unsaturated polyester, melamine, FRP, PVC, ABS, EVA and PP.

[0232] Applications of the present disclosure include keypads, o-rings, packing, belts, panels and hoses.

[0233] The compound and the release composition of the present disclosure have been described in detail above. Note that the compound and the release composition of the present disclosure are not limited to the above examples. EXAMPLES

[0234] The fluorosilicone compound and release composition of the present disclosure will be described below in the following examples, but the present disclosure is not limited to the following examples. In the present examples, the order of the repeating units constituting the siloxane portion is arbitrary, and the chemical formula shown below shows the average composition.

[0235] Synthesis Example 1 A 100 ml three-neck round-bottom flask was equipped with a stirrer, a thermometer / temperature controller, and a dropping funnel. THF (45 g), 4-trifluoromethoxyphenol (5.1 g), and potassium carbonate (8.3 g) were added. Allyl bromide (10.8 g) was then added dropwise, and the mixture was stirred at room temperature for 4 hours to react. Finally, purification was performed to obtain CFO(C6H4)OCH2CHCH2 (compound 1).

[0236] [ka]

[0237] Synthesis Example 2 A 250 mL 4-neck round bottom flask was equipped with a mechanical stirrer, a thermometer / controller, a heating mantle, a water-cooled reflux condenser with a drying tube packed with CaSO4, and an addition funnel. Me3SiO-(Me2SiO) n -(MeHSiO) mSiloxane (2.0 g) having the structure -SiMe3 (Me is a methyl group, n is 38, and m is 36) was added to a flask and heated to 60°C, followed by the addition of CFO(CH)OCHCHCH2 (compound 1, 2.24 g) containing Pt (17 mg) as a complex with 1,2-divinyltetramethyldisiloxane. Vinyltrimethoxysilane (0.4 g) was then added dropwise. Excess olefin was then removed by heating under vacuum. Finally, filtration was performed to obtain compound 2.

[0238] Synthesis Example 3 Compound 3 was produced by the same procedure as in Synthesis Example 2, except that the amount of CF3O(C6H4)OCH2CHCH2 (Compound 1) used was 2.51 g.

[0239] Synthesis Example 4 Compound 4 was produced by the same procedure as in Synthesis Example 2, except that the amount of CF3O(C6H4)OCH2CHCH2 (Compound 1) used was 2.67 g and the amount of vinyltrimethoxysilane used was 0.2 g.

[0240] [ka] Compound 2: x=29, y=7, z=38 Compound 3: x=32, y=4, z=38 Compound 4: x=34, y=2, z=38

[0241] As control compounds, the following target compounds 1 and 2 were prepared. Control compound 1: x=36, y=0, z=38 Control compound 2: x=0, y=36, z=38

[0242] Working Example A release test was carried out using the above compounds 2 to 4, control compounds 1 and 2, a compound synthesized according to the method described in Synthesis Example 1 of Japanese Patent No. 5184382 (control compound 3), and a commercially available release agent (DAIFREE GF-700, manufactured by Daikin Industries, Ltd.) (control compound 4).

[0243] (evaluation) "Mold release test" The release composition was diluted with isohexane to a solid content of 0.5 mass %, and the solution was spray-coated on an aluminum plate of 9.5 cm × 9.5 × 0.15 cm. The coated plate was then dried at 150 ° C for 15 minutes, and the non-volatile content was 0.2 to 0.3 mg / cm. 2 The duct tape with holes was then attached to an aluminum plate. Next, a CFRP prepreg (3K plain weave carbon, manufactured by Nippon Composites Co., Ltd.) 3.0 cm x 3.0 cm was attached to the painted plate and covered with an aluminum plate to prepare a test sample for molding. The prepared test sample was clamped in a press and heated to 150°C for 10 minutes while applying a pressure of 10 MPa to harden and mold the CFRP prepreg. After cooling the test sample, the aluminum plate that covered it was removed and the test sample was set in a push-pull gauge. The metal fittings of the push-pull gauge were attached to the holes in the duct tape in the test sample, and the duct tape was pulled up at a constant rhythm to release the molded CFRP prepreg from the painted plate. The force required to pull it up was measured as the release force. In addition, the same mold was used to continuously release the articles, and the number of continuous releases until it became impossible to release the articles was recorded. (i.e., the number of demolds) was measured.

[0244] "Non-transferability evaluation" The release surface of the CFRP prepreg after the release test was observed with a SEM (JCM-7000, JEOL). The components derived from the release agent on the surface were identified using SEM-EDX, and their amounts were compared. The fewer the components derived from the release agent, the better the non-transferability was, and the comparison results were classified as follows: ○: Almost no residual components derived from the release agent (very good non-transferability) △: There is a small amount of residual components from the release agent (good non-transferability) ×: Release agent-derived components remain, and the amount is large (poor non-transferability)

[0245] "Paint film adhesion evaluation" An acrylic urethane paint (NY Polyn K, manufactured by Shinto Paint Co., Ltd.) was applied to the release surface of the CFRP prepreg after the release test using a spray gun and dried at room temperature for 12 hours. The adhesion of the coating film to the prepreg was evaluated by a cross-cut test in accordance with JIS K5600. Specifically, a 5×5 grid was formed on the coating film using a cutter knife so that each grid was 2 mm long and 2 mm wide. Cellophane tape (registered trademark) was applied to the coating film after the grid was formed, pressed with a finger, and then the cellophane tape was peeled off. The remaining rate of the coating film was calculated from the grids remaining on the prepreg, and the results were classified as follows. ◎: Coating film remaining rate is 80% or more (very good adhesion) ○: Residual rate of coating film is 60-80% or more (good non-transferability) △: Residual rate of coating film is 20-60% or more (poor non-transferability) ×: Residual rate of coating film is less than 20% (non-transferability is very poor)

[0246] TIFF2024176822000010.tif19120

[0247] [Table 1]

[0248] From the above results, the fluorosilicone compound of the present invention exhibited good releasability and anti-transferability, whereas the compound of the comparative example exhibited neither releasability nor anti-transferability. [Industrial Applicability]

[0249] The fluorosilicone compounds of the present disclosure can be usefully used as mold release agents.

Claims

1. Formula (I): 【Chemistry 1】 [In the formula: R Ａ is 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 NCO-, R １ , R ２ , R ４ , R ５ , R ６ , R ７ , R ８ and R ９ are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group; R ３ and R １０ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, R Ａ -X- or R Ｓｉ -Y-, X and Y are each independently a divalent organic group; R Ｓｉ is a monovalent group containing a Si atom having a hydroxyl group or a hydrolyzable group bonded thereto, m is an integer from 1 to 100; n is an integer from 1 to 50; o is an integer from 0 to 200; The repeating units enclosed in parentheses with m, n, and o may be present in any order. A fluorosilicone compound represented by the formula:

2. R Ａ CF ３ O-, CF ３ NH- or (CF ３ ) ２ The fluorosilicone compound of claim 1 which is N-.

3. R １ , R ２ , R ４ , R ５ , R ６ , R ７ , R ８ and R ９ are each independently １－４ The fluorosilicone compound of claim 1 which is an alkyl group.

4. R ３ and R １０ are each independently １－４ The fluorosilicone compound of claim 1 which is an alkyl group.

5. X is, -(Ar) ａ１ -(CFH) ｂ１ -(CH ２ ) ｃ１ -(O) ｄ１ - [In the formula: Ar is a fluorine atom or R Ａ is a divalent aromatic group optionally substituted by a1 is an integer from 0 to 10, b1 is an integer from 0 to 200, c1 is an integer from 0 to 200, d1 is an integer from 0 to 10, The repeating units denoted by symbols a1, b1, c1, and d1 and enclosed in parentheses may be present in any order.] The fluorosilicone compound according to claim 1 , wherein the fluorosilicone compound is a group represented by the formula:

6. X is, -(Ar) ａ１ -(O) ｄ１ -(CH ２ ) ｃ１ - [In the formula: Ar is a fluorine atom or R Ａ is an optionally substituted divalent aromatic group, preferably an unsubstituted divalent aromatic group, a1 is 0 or 1; c1 is an integer from 1 to 36, d1 is 0 or 1. The fluorosilicone compound according to claim 1 , wherein the fluorosilicone compound is a group represented by the formula:

7. 2. The fluorosilicone compound of claim 1, wherein Y is an alkylene group or an alkyleneoxyalkylene group.

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

9. A mold release composition comprising the fluorosilicone compound according to any one of claims 1 to 8.

10. The mold release composition according to claim 9 , further comprising a liquid medium which is at least one selected from water and an organic solvent.

11. 10. The mold release composition according to claim 9, which is a solution or aerosol containing an organic solvent, or a water-based emulsion containing water.

12. 10. The mold release composition of claim 9, further comprising a cure-accelerating catalyst in an amount of 0.05 parts by weight to 10 parts by weight based on 100 parts by weight of the fluorosilicone compound (I).

13. The mold release composition according to claim 9, further comprising at least one selected from the group consisting of silicone oil, silicone resin, synthetic wax, natural wax, fluorine oil and fluorine resin in an amount of 0.1 parts by weight to 99 parts by weight based on 100 parts of the fluorosilicone compound (I).

14. A coating obtained from the mold release composition according to claim 9.

15. (i) a step of applying the mold release composition according to claim 9 to the inner surface of a mold to form a coating of the mold release composition. A method for forming a release agent coating comprising the steps of:

16. (i) applying the mold release composition according to claim 9 to the inner surface of a molding die to form a coating of the mold release composition; (ii) filling a molding composition into a mold having a coating of the mold release composition to obtain a molded body; and (iii) Step of removing the molded body from the mold A method for producing a molded body, comprising the steps of:

Images