Fluorosilicone compounds

Abstract

The present invention provides a fluorosilicone compound represented by formula (I). [In the formula, each symbol is as defined in the description. ]

Description

Technical Field

[0001] This invention relates to fluorosilicone compounds. Background Technology

[0002] Silicone compounds with fluorine-containing groups are known to be used, for example, as mold release agents for molding various rubbers and resins (see Patent Document 1).

[0003] Existing technical documents Patent documents Patent Document 1: Japanese Patent Publication No. 2009-541498 Summary of the Invention

[0004] The problem that the invention aims to solve The purpose of this invention is to provide a fluorosilicone compound with excellent mold release properties.

[0005] Technical means for solving the problem [1] A fluorosilicone compound represented by formula (I). [In the formula,] R A For CF3-, CF3O-, CF3NH-, CF3CH2NH-, (CF3)2N-, (CF3CH2)2N-, CF3S-, CF3C(=O)-, CF3CH2C(=O)-, CF3C(=O)O-, CF3CH2OC(=O)-, CF3CONH-, CF3C H2CONH-, 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 Each can be independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. R 3 and R 10 Each is independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or an R group. A -X-, or R Si -Y-, X and Y are each an independent divalent organic group. RSi It is a monovalent group containing Si atoms bonded with hydroxyl or hydrolyzable groups. 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 order in which the repeating units labeled m, n, and o, enclosed in parentheses, exist is arbitrary. [2] The fluorosilicone compound as described in [1] above, wherein R A It can be CF3O-, CF3NH- or (CF3)2N-.

[0006] [3] A fluorosilicone compound as described in [1] or [2] above, wherein R 1 R 2 R 4 R 5 R 6 R 7 R 8 and R 9 C independently 1－4 alkyl.

[0007] [4] The fluorosilicone compound as described in any one of [1] to [3] above, wherein R 3 and R 10 C independently 1－4 alkyl.

[0008] [5] The fluorosilicone compound as described in any one of [1] to [4] above, wherein, X is -(Ar) a1 -(CFH) b1 -(CH2) c1 -(O) d1 - The group shown.

[0009] [In the formula,] Ar can be converted by fluorine atoms or R A Substituted divalent aromatic groups, 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 order in which the repeating units labeled a1, b1, c1, and d1, enclosed in parentheses, exist is arbitrary. [6] The fluorosilicone compound as described in any one of [1] to [5] above, wherein, X is -(Ar) a1 -(O) d1-(CH2) c1 - The group shown.

[0010] [In the formula,] Ar can be converted by fluorine atoms or R A The substituted divalent aromatic group, preferably the unsubstituted divalent aromatic group, a1 is 0 or 1. c1 is an integer from 1 to 36. d1 is either 0 or 1. [7] A fluorosilicone compound as described in any one of [1] to [6] above, wherein Y is an alkylene or an alkoxyalkylene.

[0011] [8] The fluorosilicone compound as described in any one of [1] to [7] above, wherein, R Si It is a group represented by the following formula (S1), (S2), (S3), (S4) or (S5). [In the formula,] R 11 Each is independently a hydroxyl group or a hydrolyzable group. R 12 Each is an organic group that is independently monovalent. n1 in each (SiR) 11 n1 R 12 3－n1 Each unit contains an independent integer from 0 to 3. X 11 Each can be an organic group that is either a single bond or divalent. R 13 Each can be an independent hydrogen atom or a monovalent organic group. t are each an independent integer greater than 2. R 14 Each can be independently a hydrogen atom, a halogen atom, or -X. 11 -SiR 11 n1 R 12 3－n1 , R 15 Each is independently a single bond, an oxygen atom, an alkylene group having 1 to 6 carbon atoms, or an alkene group having 1 to 6 carbon atoms. R a1 Each independently is -Z 1 -SiR 21 p1 R 22 q1 R 23r1 , Z 1 Each is an independent divalent organic group. R 21 Each independently is -Z 1' -SiR 21' p1' R 22' q1' R 23' r1' , R 22 Each is independently a hydroxyl group or a hydrolyzable group. R 23 Each is an organic group that is independently monovalent. p1 can be an independent integer from 0 to 3. q1 can be an integer from 0 to 3, respectively. r1 can be an integer from 0 to 3, respectively. Z 1' Each is an independent divalent organic group. R 21' Each independently is -Z 1'' -SiR 22'' q1'' R 23'' r1'' , R 22' Each is independently a hydroxyl group or a hydrolyzable group. R 23' Each is an organic group that is independently monovalent. p1' are independent integers from 0 to 3. q1' are independent integers from 0 to 3. r1' are independent integers from 0 to 3. Z 1'' Each is an independent divalent organic group. R 22'' Each is independently a hydroxyl group or a hydrolyzable group. R 23'' Each is an organic group that is independently monovalent. q1'' can be an integer from 0 to 3, respectively. r1'' can be an integer from 0 to 3, respectively. R b1 Each is independently a hydroxyl group or a hydrolyzable group. R c1 Each is an organic group that is independently monovalent. k1 are independent integers from 0 to 3. l1 can be an independent integer from 0 to 3. m1 can be an independent integer from 0 to 3. R d1 Each independently is -Z 2 -CR 31 p2 R 32 q2 R 33 r2 , Z 2 Each can be an independent single bond, an oxygen atom, or a divalent organic group. R 31 Each independently is -Z 2' -CR 32' q2' R 33' r2' , R 32 Each independently is -Z 3 -SiR 34 n2 R 35 3－n2 , R 33 Each of these can be an independent hydrogen atom, a hydroxyl group, or a monovalent organic group. p2 are independent integers from 0 to 3. q2 can be an integer from 0 to 3, respectively. r2 are independent integers from 0 to 3. Z 2' Each can be an independent single bond, an oxygen atom, or a divalent organic group. R 32' Each independently is -Z 3 -SiR 34 n2 R 35 3－n2 , R 33' Each of these can be an independent hydrogen atom, a hydroxyl group, or a monovalent organic group. q2' are independent integers from 0 to 3. r2' are independent integers from 0 to 3. Z 3 Each can be an independent single bond, an oxygen atom, or a divalent organic group. R 34 Each is independently a hydroxyl group or a hydrolyzable group. R 35 Each is an organic group that is independently monovalent. n2 are independent integers from 0 to 3. R e1Each independently is -Z 3 -SiR 34 n2 R 35 3－n2 , R f1 Each of these can be an independent hydrogen atom, a hydroxyl group, or a monovalent organic group. k2 are independent integers from 0 to 3. l2 can be independent integers from 0 to 3. m2 can be independent integers from 0 to 3. R g1 and R h1 Each independently is -Z 4 -SiR 11 n1 R 12 3－n1 -Z 4 -SiR a1 k1 R b1 l1 R c1 m1 or -Z 4 -CR d1 k2 R e1 l2 R f1 m2 , Z 4 Each can be an independent single bond, an oxygen atom, or a divalent organic group. k3 is 1 or 2. l3 is either 0 or 1. In formulas (S1), (S2), (S3), (S4), or (S5), at least two Si atoms bonded with hydroxyl or hydrolyzable groups are present. [9] A release composition containing any one of the fluorosilicone compounds described in [1] to [8] above.

[0012]

[10] The release composition as described in [9] above further contains a liquid medium selected from water and organic solvents.

[0013]

[11] The release composition as described in [9] or

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

[0014]

[12] The release composition as described in any one of [9] to

[11] above further contains a curing promoting catalyst in an amount of 0.05 to 10 parts by weight relative to 100 parts by weight of the fluorosilicone compound (I).

[0015]

[13] The release composition as described in any one of [9] to

[12] above further contains at least one selected from silicone oil, silicone resin, synthetic wax, natural wax, fluorinated oil and fluorinated resin, in a content of 0.1 to 99 parts by weight relative to 100 parts of fluorosilicone compound (I).

[0016]

[14] A coating obtained from any of the release compositions described in any of [9] to

[13] above.

[0017]

[15] A method for forming a release agent coating, comprising: (i) applying the release composition described in any one of [9] to

[13] above onto the inner surface of a molding die to form a coating of the release composition.

[0018]

[16] A method for manufacturing a molded article, comprising: (i) The process of applying the release composition described in any one of [9] to

[13] above onto the inner surface of the molding die to form a film of the release composition; (ii) The process of filling a molding composition into a molded mold having a release composition to obtain a molded article; and (iii) The process of removing the molded part from the molding die.

[0019] Invention Effects The fluorosilicone compounds of the present invention provide excellent mold release properties. Detailed Implementation

[0020] When used in this specification, "monovalent organic group" refers to a monovalent group containing carbon. Unless otherwise specified, a monovalent organic group can be a hydrocarbon group or its derivative. A hydrocarbon derivative refers to a group having one or more N, O, S, Si, amide, sulfonyl, siloxane, carbonyl, or carbonyloxy groups at the end of the hydrocarbon group or in the molecular chain.

[0021] When used in this specification, the term "divalent organic group" is not particularly limited, and examples of divalent groups that have further removed one hydrogen atom from a hydrocarbon group can be listed.

[0022] When used in this specification, "hydrocarbon group" refers to a group containing carbon and hydrogen, specifically a group that has lost one hydrogen atom from the molecule. There is no particular limitation on such a hydrocarbon group; examples include hydrocarbon groups with 1 to 20 carbon atoms, such as aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The aforementioned "aliphatic hydrocarbon group" can be any type of linear, branched, or cyclic structure, and can be any type of saturated or unsaturated structure. Furthermore, the hydrocarbon group can also contain one or more ring structures. Such a hydrocarbon group can also be substituted by one or more substituents. Moreover, such a hydrocarbon group can have one or more N, O, S, Si, amide, sulfonyl, siloxane, carbonyl, or carbonyloxy groups at its terminal or in the molecular chain.

[0023] When used in this specification, the term "hydrocarbon group" is not particularly limited, and examples include: halogen atoms; and atoms selected from C that can be substituted by one or more halogen atoms. 1－6 Alkyl, C 2－6 alkenyl, C 2－6 alkynyl group, C 3－10 cycloalkyl, C 3－10 Unsaturated cycloalkyl groups, 5-10 membered heterocyclic groups, 5-10 membered unsaturated heterocyclic groups, C 6－10 One or more groups selected from aryl and 5- to 10-membered heteroaryl groups.

[0024] As used in this specification, "hydrolyzable group" refers to a group capable of undergoing a hydrolysis reaction; that is, a group that can be released from the main skeleton of a compound through a hydrolysis reaction. Examples of hydrolyzable groups include -OR h -OCOR h -O-N=CR h 2. -NR h 2. -NHR h Or -NCO (in these formulas, R) h (representing alkyl groups with 1 to 4 carbon atoms, whether substituted or unsubstituted), preferably -OR h (i.e., alkoxy group). R h Examples include: non-substituted alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, and isobutyl; and substituted alkyl groups such as chloromethyl. Among these, alkyl groups are preferred, especially non-substituted alkyl groups, and more preferably methyl or ethyl. In one embodiment, R h For methyl, in another manner, R h It is an ethyl group.

[0025] The fluorosilicone compound of the present invention is represented by formula (I). [In the formula,] R AFor CF3-, CF3O-, CF3NH-, CF3CH2NH-, (CF3)2N-, (CF3CH2)2N-, CF3S-, CF3C(=O)-, CF3CH2C(=O)-, CF3C(=O)O-, CF3CH2OC(=O)-, CF3CONH-, CF3C H2CONH-, 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 Each can be independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. R 3 and R 10 Each is independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or an R group. A -X-, or R Si -Y-, X and Y are each an independent divalent organic group. R Si It is a monovalent group containing Si atoms bonded with hydroxyl or hydrolyzable groups. 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 order in which the repeating units labeled m, n, and o, enclosed in parentheses, exist is arbitrary. R A For CF3-, CF3O-, CF3NH-, CF3CH2NH-, (CF3)2N-, (CF3CH2)2N-, CF3S-, CF3C(=O)-, CF3CH2C(=O)-, CF3C(=O)O-, CF3CH2OC(=O)-, CF3CONH-, CF3C H2CONH-, CF3NHCO-, CF3CH2NHCO-, CF3CON(CF3)-, CF3CH2CON(CF3)-, CF3CON(CH2CF3)-, CF3CH2CON(CH2CF3)-, (CF3)2NCO- or (CF3CH2)2NCO-. R APreferably, the CF3O-, CF3NH-, (CF3)2N-, CF3S-, CF3C(=O)-, CF3C(=O)O-, CF3OC(=O)-, CF3CONH-, CF3NHCO-, CF3CON(CF3)- or (CF3)2NCO- are used, and more preferably, CF3O-, CF3NH- or (CF3)2N- are used.

[0026] In one approach, R A It can be CF3O-.

[0027] In another way, R A It can be CF3NH- or (CF3)2N-, preferably CF3NH-.

[0028] R 1 R 2 R 4 R 5 R 6 R 7 R 8 and R 9 Each is independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0029] Substituents for the aforementioned alkyl and aryl groups include: halogen atoms; and atoms selected from C10 that can be substituted by one or more halogen atoms. 1－6 Alkyl, C 2－6 alkenyl, C 2－6 alkynyl group, C 3－10 cycloalkyl, C 3－10 Unsaturated cycloalkyl groups, 5-10 membered heterocyclic groups, 5-10 membered unsaturated heterocyclic groups, C 6－10 One or more groups selected from aryl and 5- to 10-membered heteroaryl groups. The halogen atom is a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, preferably a chlorine atom.

[0030] In one embodiment, the alkyl group can be an alkyl group that can be substituted by halogen atoms such as chlorine atoms.

[0031] In one embodiment, the aryl group can be a halogen atom such as a chlorine atom, or a C1-C atom such as a methyl group. 10 Alkyl-substituted aryl groups.

[0032] The alkyl group mentioned above is preferably C10. 1－20 Alkyl, more preferably C 1－12 Alkyl, more preferably C 1－4 Alkyl groups, more preferably methyl groups.

[0033] The aryl group is preferably C. 6－20 Aryl, more preferably C 6－12Aryl, more preferably phenyl.

[0034] In one approach, R 1 R 2 R 4 R 5 R 6 R 7 R 8 and R 9 It can be independently non-substituted alkyl groups such as methyl, ethyl, propyl, hexyl, and dodecyl; substituted alkyl groups such as chloromethyl; non-substituted aryl groups such as phenyl and naphthyl; and substituted aryl groups such as 4-chlorophenyl and 2-methylphenyl. Among these, alkyl groups are preferred, especially non-substituted alkyl groups, and methyl groups are more preferred.

[0035] R 3 and R 10 Each is independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or an R group. A -X- or R Si -Y-.

[0036] R 3 and R 10 The meanings of substituted or unsubstituted alkyl and substituted or unsubstituted aryl groups in R are the same as those in the above. 1 The same as those recorded in the document.

[0037] In one approach, R 3 and R 10 Each is independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

[0038] In another way, it is R A -X- or R Si -Y-.

[0039] X is an organic group that is divalent.

[0040] In one mode, X is -(Ar). a1 -(CFH) b1 -(CH2) c1 -(O) d1 - The group shown.

[0041] [In the formula,] Ar can be converted by fluorine atoms or R A Substituted divalent aromatic groups, R AFor CF3-, CF3O-, CF3NH-, CF3CH2NH-, (CF3)2N-, (CF3CH2)2N-, CF3S-, CF3C(=O)-, CF3CH2C(=O)-, CF3C(=O)O-, CF3CH2OC(=O)-, CF3CONH-, CF3C H2CONH-, 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 order in which the repeating units labeled a1, b1, c1, and d1, enclosed in parentheses, exist is arbitrary. Furthermore, in the preferred formulation, oxygen atoms are not present continuously. That is, -O-O- bonds are preferably absent. Additionally, the left side of X is connected to R... A Bonding.

[0042] The aforementioned aromatic groups include not only aromatic rings containing only carbon as cyclic atoms (so-called aryl groups), but also aromatic rings containing nitrogen, oxygen, or sulfur as cyclic atoms (so-called heteroaryl groups), as well as groups having multiple aromatic rings.

[0043] The aromatic groups mentioned above preferably have benzene rings, naphthyl rings, phenanthrene rings, anthracene rings, tetraphenyl rings, pentaphenyl rings, benzo[a]pyrene rings, cyclo[b]pyrene rings, triphenylene rings, cyclopentene rings, ovobenzyl rings, indole rings, furan rings, thiophene rings, pyrrole rings, pyrazole rings, imidazole rings, pyridine rings, pyridazine rings, pyrimidine rings, biphenyl rings, terphenyl rings, triphenylmethane rings, or benzophenone rings.

[0044] In one embodiment, the aromatic group preferably has a benzene ring, a naphthalene ring, a phenanthrene ring, an anthracene ring, a tetraphenyl ring, a pentaphenyl ring, a benzo[a]pyrene ring, a cyclo[b]pyrene ring, a triphenylene ring, a cycloene ring, or an ovoid ring, more preferably a benzene ring or a naphthalene ring, and even more preferably a benzene ring.

[0045] 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, and more preferably an indole ring.

[0046] In another embodiment, the aromatic group preferably has a biphenyl ring, a terphenyl ring, a triphenylmethane ring, or a benzophenone ring.

[0047] In one embodiment, Ar is an unsubstituted divalent aromatic group.

[0048] In another configuration, Ar is a fluorine atom or R A Substituted divalent aromatic groups.

[0049] In another way, Ar is R A Substituted divalent aromatic groups.

[0050] In another embodiment, Ar is a divalent aromatic group substituted with a fluorine atom.

[0051] The number of substituents in the aforementioned aromatic groups is not particularly limited; for example, it can be 1 to 10, 1 to 5, 1 to 3, 1, 2, or 3. In one embodiment, the number of substituents in the aforementioned aromatic groups is one or more. In another embodiment, the aforementioned aromatic groups can be fully substituted.

[0052] a1 is an integer from 0 to 10, preferably 0 or 1.

[0053] In one mode, a1 is 0.

[0054] In another way, a1 is 1.

[0055] b1 is an integer from 0 to 200, preferably an integer from 0 to 6.

[0056] c1 is an integer from 0 to 200, preferably an integer from 0 to 30.

[0057] d1 is an integer from 0 to 10, preferably an integer from 0 to 3.

[0058] In one mode, X is -(Ar). a1 -(O) d1 -(CH2) c1 - The group shown.

[0059] [In the formula,] Ar can be converted by fluorine atoms or R A The substituted divalent aromatic group, preferably the unsubstituted divalent aromatic group, a1 is 0 or 1. c1 is an integer from 1 to 36, preferably an integer from 1 to 30, for example, it can be an integer from 1 to 9, an integer from 1 to 3, or an integer from 2 to 3. d1 is either 0 or 1. In one configuration, X is -(CH2). c1 - The group shown.

[0060] [In the formula, c1 is an integer from 1 to 36, preferably an integer from 1 to 30, for example, an integer from 1 to 9 or an integer from 1 to 3.] In one configuration, X is -Ar-O-(CH2). c1 - The group shown.

[0061] [In the formula,] Ar can be converted by fluorine atoms or R A The substituted divalent aromatic group, preferably the unsubstituted divalent aromatic group, c1 is an integer from 1 to 36, preferably an integer from 1 to 30, for example, an integer from 1 to 9, an integer from 1 to 3, or an integer from 2 to 3. Y is an independent divalent organic group.

[0062] Y is preferably a divalent organic group with 1 to 20 carbon atoms, more preferably with 1 to 12 carbon atoms.

[0063] Y is preferably an alkylene group (preferably with 1 to 20 carbon atoms, more preferably with 1 to 12 carbon atoms), such as ethylene, propyleneene, methyl ethylene, octylene, and dodecylene, and alkoxyalkylene groups (preferably with 2 to 20 carbon atoms, more preferably with 2 to 12 carbon atoms), such as ethoxymethylene, propoxymethylene, propoxyethylene, and ethoxybutylene. Y is more preferably -(CH2). r — [where r is an integer from 2 to 200, preferably an integer from 2 to 12].

[0064] R Si It is a monovalent group containing Si atoms bonded with hydroxyl or hydrolyzable groups.

[0065] R Si Preferably, the group is represented by formula (S1), (S2), (S3), (S4) or (S5). R 11 Each can be an independent hydroxyl group or a hydrolyzable group.

[0066] R 11 Preferably, each group is a hydrolyzable group.

[0067] R 12 Each is an organic group that is independently monovalent. But R 12 It does not contain hydrolyzable groups.

[0068] In R 12 In this context, the monovalent organic group is preferably C. 1－20 Alkyl, more preferably C 1－6 Alkyl group, more preferably methyl group.

[0069] n1 in each (SiR) 11 n1 R 12 3－n1 Each of the units is an independent integer from 0 to 3. Among them, in equation (S1), there exist at least two units where n1 is 1 to 3 (SiR). 11 n1 R 12 3－n1 In other words, there are at least two Si atoms bonded with hydroxyl or hydrolyzable groups in formula (S1).

[0070] n1 in each (SiR) 11 n1 R 12 3－n1 The units are preferably integers of 1 to 3, more preferably 2 to 3, and even more preferably 3.

[0071] In the above formula, X 11 Each of the organic groups is either a single bond or divalent. The divalent organic group is preferably -R. 28 -O x -R 29 - (where R is the formula) 28 and R 29 Each independently is a single bond or C 1－20 Alkylene, x is 0 or 1). The C 1－20 The alkylene group can be straight-chain or branched, preferably straight-chain. The C 1－20 Alkylene is preferably C 1－10 Alkylene, more preferably C 1－6 Alkylene, more preferably C 1－3 Alkylene.

[0072] In one manner, X 11 Each independently is -C 1－6 Alkylene-O-C 1－6 alkylene- or -O-C 1－6 Alkylene-.

[0073] In the preferred embodiment, X 11 C can be either a single bond or a straight chain, respectively. 1－6 Alkylene, preferably single-bonded or straight-chain C 1－3 Alkylene, more preferably a single bond or a straight-chain C 1－2 Alkylene, more preferably straight-chain C 1－2 Alkylene.

[0074] R 13 Each organic group is either a hydrogen atom or a monovalent organic group. Such a monovalent organic group is preferably C. 1－20alkyl.

[0075] In the preferred embodiment, R 13 Each is an independent hydrogen atom or a straight-chain C. 1－6 Alkyl groups, preferably hydrogen atoms or straight-chain C atoms. 1－3 Alkyl group, preferably a hydrogen atom or a methyl group.

[0076] R 15 Each is independently a single bond, an oxygen atom, and a carbon atom. 1－6 Alkylene or C 1－6 Alkyloxy group.

[0077] In one approach, R 15 Each is independently an oxygen atom and a carbon atom. 1－6 Alkylene or C 1－6 Alkyloxy group.

[0078] In the preferred embodiment, R 15 It is a single key.

[0079] t are each an independent integer greater than 2.

[0080] In the preferred embodiment, t is an integer from 2 to 10, preferably an integer from 2 to 6.

[0081] R 14 Each can be independently 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 It is a hydrogen atom.

[0082] In one approach, equation (S1) is the following equation (S1-a). [In the formula,] R 11 R 12 R 13 X 11 The meanings of n1 and n1 are the same as those stated in the above formula (S1). t1 and t2 are each independently an integer greater than or equal to 1, preferably an integer from 1 to 10, more preferably an integer from 2 to 10, for example, an integer from 1 to 5 or an integer from 2 to 5. The order of the repeating units labeled t1 and t2 and enclosed in parentheses is arbitrary in the formula. In the preferred embodiment, equation (S1) is the following equation (S1-b). [In the formula, R] 11 R 12 R 13 X 11 The meanings of n1 and t are the same as those stated in the above formula (S1). In the preferred embodiment, in equation (S2), -SiR 11 n1 R 12 3－n1 The Si atoms do not form siloxane bonds.

[0083] In one embodiment (S2), there are at least two Si atoms bonded with hydroxyl or hydrolyzable groups.

[0084] R a1 Each independently is -Z 1 -SiR 21 p1 R 22 q1 R 23 r1 .

[0085] The above Z 1 Each of these is an organic group that is independently an oxygen atom or a divalent organic group. Hereinafter, it is denoted as Z. 1 The right side of the structure and (SiR) 21 p1 R 22 q1 R 23 r1 ) bond.

[0086] In the preferred method, Z 1 It is a divalent organic group.

[0087] In the preferred method, Z 1 Excluding Z 1 The bonded Si atoms form siloxane bonds. Preferably, in formula (S3) (Si-Z) 1 -Si) does not contain siloxane bonds.

[0088] The above Z 1 C is preferred 1－6 Alkylene, -(CH2) z1 -O-(CH2) z2 - (where z1 is an integer from 0 to 6, for example, an integer from 1 to 6, and z2 is an integer from 0 to 6, for example, an integer from 1 to 6) or - (CH2) z3 -Phenylidene-(CH2) z4 —(In the formula, z3 is an integer from 0 to 6, for example, an integer from 1 to 6; z4 is an integer from 0 to 6, for example, an integer from 1 to 6). This C1－6 The alkylene group can be straight-chain or branched, preferably straight-chain. These groups can be selected from, for example, fluorine atoms, C atoms, etc. 1－6 Alkyl, C 2－6 alkenyl and C 2－6 One or more substituents in the alkynyl group are substituted, but preferably unsubstituted.

[0089] In the preferred method, Z 1 C 1－6 Alkylene or -(CH2) z3 -Phenylidene-(CH2) z4 -, preferably -phenylene-(CH2) z4 -.

[0090] In another preferred embodiment, the aforementioned Z 1 C 1－3 Alkylene. In one manner, Z 1 It can be -CH2CH2CH2-. In another way, Z 1 It can be -CH2CH2-.

[0091] R 21 Each independently is -Z 1' -SiR 21' p1' R 22' q1' R 23' r1' .

[0092] The above Z 1' Each of these is an organic group that is independently an oxygen atom or a divalent organic group. Hereinafter, it is denoted as Z. 1' The right side of the structure and (SiR) 21' p1' R 22' q1' R 23' r1' ) bond.

[0093] In the preferred method, Z 1' It is a divalent organic group.

[0094] In the preferred method, Z 1' Excluding Z 1' The bonded Si atoms form siloxane bonds. Preferably, in formula (S3) (Si-Z) 1' -Si) does not contain siloxane bonds.

[0095] The above Z 1' C is preferred 1－6 Alkylene, -(CH2) z1' -O-(CH2)z2' - (where z1' is an integer from 0 to 6, for example, an integer from 1 to 6, and z2' is an integer from 0 to 6, for example, an integer from 1 to 6) or - (CH2) z3' -Phenylidene-(CH2) z4' —(In the formula, z3' is an integer from 0 to 6, for example, an integer from 1 to 6, and z4' is an integer from 0 to 6, for example, an integer from 1 to 6). These C 1－6 The alkylene group can be straight-chain or branched, preferably straight-chain. These groups can be selected from, for example, fluorine atoms, C atoms, etc. 1－6 Alkyl, C 2－6 alkenyl and C 2－6 One or more substituents in the alkynyl group are substituted, but preferably unsubstituted.

[0096] In the preferred method, Z 1' C 1－6 Alkylene or -(CH2) z3' -Phenylidene-(CH2) z4' -, preferably -phenylene-(CH2) z4' -.

[0097] In another preferred embodiment, the aforementioned Z 1' C 1－3 Alkylene. In one manner, Z 1' It can be -CH2CH2CH2-. In another way, Z 1' It can be -CH2CH2-.

[0098] R 21' Each independently is -Z 1'' -SiR 22'' q1'' R 23'' r1'' .

[0099] Z 1'' Each of these is an organic group that is independently an oxygen atom or a divalent organic group. Hereinafter, it is denoted as Z. 1'' The right side of the structure and (SiR) 22'' q1'' R 23'' r1'' ) bond.

[0100] In the preferred method, Z 1'' It is a divalent organic group.

[0101] In the preferred method, Z 1'' Excluding Z 1'' The bonded Si atoms form siloxane bonds. Preferably, in formula (S3) (Si-Z) 1'' -Si) does not contain siloxane bonds.

[0102] Z 1'' C is preferred 1－6 Alkylene, -(CH2) z1'' -O-(CH2) z2'' - (where z1'' is an integer from 0 to 6, for example, an integer from 1 to 6, and z2'' is an integer from 0 to 6, for example, an integer from 1 to 6) or - (CH2) z3'' -Phenylidene-(CH2) z4'' —(In the formula, z3'' is an integer from 0 to 6, for example, an integer from 1 to 6, and z4'' is an integer from 0 to 6, for example, an integer from 1 to 6). These C 1－6 The alkylene group can be straight-chain or branched, preferably straight-chain. These groups can be selected from, for example, fluorine atoms, C atoms, etc. 1－6 Alkyl, C 2－6 alkenyl and C 2－6 One or more substituents in the alkynyl group are substituted, but preferably unsubstituted.

[0103] In the preferred method, Z 1'' C 1－6 Alkylene or -(CH2) z3'' -Phenylidene-(CH2) z4'' -, preferably -phenylene-(CH2) z4'' - In Z 1'' When such a group is present, light tolerance, especially UV tolerance, is further improved.

[0104] In another preferred embodiment, the aforementioned Z 1'' C 1－3 Alkylene. In one manner, Z 1'' It can be -CH2CH2CH2-. In another way, Z 1'' It can be -CH2CH2-.

[0105] R 22'' Each can be an independent hydroxyl group or a hydrolyzable group.

[0106] R 22'' Preferably, each group is a hydrolyzable group.

[0107] R 23'' Each of these is an organic group that is independently monovalent. Such monovalent organic groups are those other than the hydrolyzable groups mentioned above.

[0108] In R 23'' In this context, the monovalent organic group is preferably C. 1－20 Alkyl, more preferably C 1－6 Alkyl group, more preferably methyl group.

[0109] q1'' is an independent integer from 0 to 3, and r1'' is an independent integer from 0 to 3. The sum of q1'' and r1'' is in each (SiR) 22'' q1'' R 23'' r1'' The value in unit ) is 3.

[0110] q1'' in each (SiR 22'' q1'' R 23'' r1'' The units are preferably integers of 1 to 3, more preferably 2 to 3, and even more preferably 3.

[0111] R 22' Each can be an independent hydroxyl group or a hydrolyzable group.

[0112] R 22' Preferably, each group is a hydrolyzable group.

[0113] R 23' Each of these is an organic group that is independently monovalent. Such monovalent organic groups are those other than the hydrolyzable groups mentioned above.

[0114] In R 23' In this context, the monovalent organic group is preferably C. 1－20 Alkyl, more preferably C 1－6 Alkyl group, more preferably methyl group.

[0115] Each of the above, p1', q1', and r1', is an independent integer from 0 to 3. Furthermore, the sum of p', q1', and r1' lies within (SiR). 21' p1' R 22' q1' R 23' r1' The value in unit ) is 3.

[0116] In one mode, p1' is 0.

[0117] In one manner, p1' in each (SiR 21' p1' R 22' q1' R 23' r1' Each of the units is an integer from 1 to 3, an integer from 2 to 3, or 3. In the preferred embodiment, p1' is 3.

[0118] In one manner, q1' in each (SiR 21' p1' R 22'q1' R 23' r1' Each of the units is an integer from 1 to 3, preferably an integer from 2 to 3, and more preferably 3.

[0119] In one mode, p1' is 0, and q1' is in each (SiR 21' p1' R 22' q1' R 23' r1' Each of the units is an integer from 1 to 3, preferably an integer from 2 to 3, and more preferably 3.

[0120] R 22 Each can be an independent hydroxyl group or a hydrolyzable group.

[0121] R 22 Preferably, each group is a hydrolyzable group.

[0122] R 23 Each of these is an organic group that is independently monovalent. Such monovalent organic groups are those other than the hydrolyzable groups mentioned above.

[0123] In R 23 In this context, the monovalent organic group is preferably C. 1－20 Alkyl, more preferably C 1－6 Alkyl group, more preferably methyl group.

[0124] p1, q1, and r1 are all independent integers from 0 to 3. Furthermore, the sum of p1, q1, and r1 lies within (SiR). 21 p1 R 22 q1 R 23 r1 The value in unit ) is 3.

[0125] In one mode, p1 is 0.

[0126] In one approach, p1 in each (SiR) 21 p1 R 22 q1 R 23 r1 Each of the units is an integer from 1 to 3, an integer from 2 to 3, or 3. In the preferred embodiment, p1 is 3.

[0127] In one approach, q1 is in each (SiR) 21 p1 R 22 q1 R23 r1 Each of the units is an integer from 1 to 3, preferably an integer from 2 to 3, and more preferably 3.

[0128] In one mode, p1 is 0, and q1 is in each (SiR) 21 p1 R 22 q1 R 23 r1 Each of the units is an integer from 1 to 3, preferably an integer from 2 to 3, and more preferably 3.

[0129] R b1 Each can be an independent hydroxyl group or a hydrolyzable group.

[0130] R b1 Preferably, each group is a hydrolyzable group.

[0131] R c1 Each of these is an organic group that is independently monovalent. Such monovalent organic groups are those other than the hydrolyzable groups mentioned above.

[0132] In R c1 In this context, the monovalent organic group is preferably C. 1－20 Alkyl, more preferably C 1－6 Alkyl group, more preferably methyl group.

[0133] k1, l1, and m1 are all independent integers from 0 to 3. Furthermore, the sum of k1, l1, and m1 lies within (SiR). a1 k1 R b1 l1 R c1 m1 The value in unit ) is 3.

[0134] In one approach, k1 is in each (SiR) a1 k1 R b1 l1 R c1 m1 Each of the units is an independent integer from 1 to 3, preferably 2 or 3, more preferably 3. In the preferred embodiment, k1 is 3.

[0135] In formula (S3), there are at least two Si atoms bonded with hydroxyl or hydrolyzable groups.

[0136] In a preferred embodiment, at least two Si atoms bonded with hydroxyl or hydrolyzable groups are present at the end portion of formula (S3).

[0137] In a preferred embodiment, the group represented by formula (S3) has -Z 1 -SiR 22 q1 R 23 r1 (In the formula, q1 is an integer from 1 to 3, preferably 2 or 3, more preferably 3, and r1 is an integer from 0 to 2), -Z 1' -SiR 22' q1' R 23' r1' (In the formula, q1' is an integer from 1 to 3, preferably 2 or 3, more preferably 3, and r1' is an integer from 0 to 2) or -Z 1'' -SiR 22'' q1'' R 23'' r1'' (In the formula, q1'' is an integer from 1 to 3, preferably 2 or 3, more preferably 3, and r1'' is an integer from 0 to 2) any one of them. Z 1 Z 1' Z 1'' R 22 R 23 R 22' R 23' R 22'' and R 23'' The meaning is the same as above.

[0138] In the preferred embodiment, R exists in equation (S3). 21' At that time, in at least one, preferably all of R 21' In this context, q1'' is an integer from 1 to 3, preferably 2 or 3, and more preferably 3.

[0139] In the preferred embodiment, R exists in equation (S3). 21 At that time, in at least one, preferably all of R 21 In this context, p1' is 0, and q1' is an integer from 1 to 3, preferably 2 or 3, and more preferably 3.

[0140] In the preferred embodiment, R exists in equation (S3). a1 At that time, in at least one, preferably all of R a1 In this case, p1 is 0, and q1 is an integer from 1 to 3, preferably 2 or 3, and more preferably 3.

[0141] In the preferred embodiment, in formula (S3), k1 is 2 or 3, preferably 3, p1 is 0, and q1 is 2 or 3, preferably 3.

[0142] R d1 Each independently is -Z 2 -CR 31 p2R 32 q2 R 33 r2 .

[0143] Z 2 Each of these can be an organic group that is independently a single bond, an oxygen atom, or a divalent organic group. Furthermore, it will be hereinafter denoted as Z. 2 The right side of the structure and (CR) 31 p2 R 32 q2 R 33 r2 ) bond.

[0144] In the preferred method, Z 2 It is a divalent organic group.

[0145] In the preferred method, Z 2 It does not contain siloxane bonds.

[0146] Z 2 C is preferred 1－6 Alkylene, -(CH2) z5 -O-(CH2) z6 - (where z5 is an integer from 0 to 6, for example, an integer from 1 to 6, and z6 is an integer from 0 to 6, for example, an integer from 1 to 6) or - (CH2) z7 -Phenylidene-(CH2) z8 —(In the formula, z7 is an integer from 0 to 6, for example, an integer from 1 to 6; z8 is an integer from 0 to 6, for example, an integer from 1 to 6). Such a C 1－6 The alkylene group can be straight-chain or branched, preferably straight-chain. These groups can be selected from, for example, fluorine atoms, C atoms, etc. 1－6 Alkyl, C 2－6 alkenyl and C 2－6 One or more substituents in the alkynyl group are substituted, but preferably unsubstituted.

[0147] In the preferred method, Z 2 C 1－6 Alkylene or -(CH2) z7 -Phenylidene-(CH2) z8 -, preferably -phenylene-(CH2) z8 -. Z 2 When such a group is present, light tolerance, especially UV tolerance, is further improved.

[0148] In another preferred embodiment, the aforementioned Z 2 C 1－3 Alkylene. In one manner, Z 2 It can be -CH2CH2CH2-. In another way, Z2 It can be -CH2CH2-.

[0149] R 31 Each independently is -Z 2' -CR 32' q2' R 33' r2' .

[0150] Z 2' Each of these can be an organic group that is independently a single bond, an oxygen atom, or a divalent organic group. Furthermore, it will be hereinafter denoted as Z. 2' The right side of the structure and (CR) 32' q2' R 33' r2' ) bond.

[0151] In the preferred method, Z 2' It does not contain siloxane bonds.

[0152] Z 2' C is preferred 1－6 Alkylene, -(CH2) z5' -O-(CH2) z6' - (where z5' is an integer from 0 to 6, for example, an integer from 1 to 6, and z6' is an integer from 0 to 6, for example, an integer from 1 to 6) or - (CH2) z7' -Phenylidene-(CH2) z8' —(In the formula, z7' is an integer from 0 to 6, for example, an integer from 1 to 6; z8' is an integer from 0 to 6, for example, an integer from 1 to 6). Such a C 1－6 The alkylene group can be straight-chain or branched, preferably straight-chain. These groups can be selected from, for example, fluorine atoms, C atoms, etc. 1－6 Alkyl, C 2－6 alkenyl and C 2－6 One or more substituents in the alkynyl group are substituted, but preferably unsubstituted.

[0153] In the preferred method, Z 2' C 1－6 Alkylene or -(CH2) z7' -Phenylidene-(CH2) z8' -, preferably -phenylene-(CH2) z8' -. Z 2' When such a group is present, light tolerance, especially UV tolerance, is further improved.

[0154] In another preferred embodiment, the aforementioned Z 2' C 1－3 Alkylene. In one manner, Z 2'It can be -CH2CH2CH2-. In another way, Z 2' It can be -CH2CH2-.

[0155] R 32' Each independently is -Z 3 -SiR 34 n2 R 35 3－n2 .

[0156] Z 3 Each of these can be an organic group that is independently a single bond, an oxygen atom, or a divalent organic group. Furthermore, it will be hereinafter denoted as Z. 3 The right side of the structure and (SiR) 34 n2 R 35 3－n2 ) bond.

[0157] In one approach, Z 3 It is an oxygen atom.

[0158] In one approach, Z 3 It is a divalent organic group.

[0159] In the preferred method, Z 3 It does not contain siloxane bonds.

[0160] Z 3 C is preferred 1－6 Alkylene, -(CH2) z5'' -O-(CH2) z6'' - (where z5'' is an integer from 0 to 6, for example, an integer from 1 to 6, and z6'' is an integer from 0 to 6, for example, an integer from 1 to 6) or - (CH2) z7'' -Phenylidene-(CH2) z8'' —(In the formula, z7'' is an integer from 0 to 6, for example, an integer from 1 to 6; z8'' is an integer from 0 to 6, for example, an integer from 1 to 6). Such a C 1－6 The alkylene group can be straight-chain or branched, preferably straight-chain. These groups can be selected from, for example, fluorine atoms, C atoms, etc. 1－6 Alkyl, C 2－6 alkenyl and C 2－6 One or more substituents in the alkynyl group are substituted, but preferably unsubstituted.

[0161] In the preferred method, Z 3 C 1－6 Alkylene or -(CH2) z7'' -Phenylidene-(CH2) z8'' -, preferably -phenylene-(CH2) z8'' -. Z 3When such a group is present, light tolerance, especially UV tolerance, is further improved.

[0162] In another preferred embodiment, the aforementioned Z 3 C 1－3 Alkylene. In one manner, Z 3 It can be -CH2CH2CH2-. In another way, Z 3 It can be -CH2CH2-.

[0163] R 34 Each can be an independent hydroxyl group or a hydrolyzable group.

[0164] R 34 Preferably, each group is a hydrolyzable group.

[0165] R 35 Each of these is an organic group that is independently monovalent. Such monovalent organic groups are those other than the hydrolyzable groups mentioned above.

[0166] In R 35 In this context, the monovalent organic group is preferably C. 1－20 Alkyl, more preferably C 1－6 Alkyl group, more preferably methyl group.

[0167] In the above formula, n2 is in each (SiR) 34 n2 R 35 3－n2 Each of the units is an independent integer from 0 to 3. At least two (SiR) units with n² values ​​of 1 to 3 exist at the end of equation (S4). 34 n2 R 35 3－n2 In other words, at least two Si atoms bonded with hydroxyl or hydrolyzable groups exist at the end of formula (S4).

[0168] n2 in each (SiR) 34 n2 R 35 3－n2 The units are preferably integers of 1 to 3, more preferably 2 to 3, and even more preferably 3.

[0169] The above R 33' Each of these can be an organic group that is independently a hydrogen atom, a hydroxyl group, or a monovalent organic group. Such a monovalent organic group is a monovalent organic group other than the hydrolyzable groups mentioned above.

[0170] In the above R 33' In this context, the monovalent organic group is preferably C. 1－20 Alkyl or - (C s H2s ) t1 - (O-C) s H 2s ) t2 (In the formula, s is an integer from 1 to 6, preferably an integer from 2 to 4; t1 is 1 or 0, preferably 0; t2 is an integer from 1 to 20, preferably an integer from 2 to 10, more preferably an integer from 2 to 6), more preferably C. 1－20 Alkyl, more preferably C 1－6 Alkyl groups, particularly preferably methyl groups.

[0171] In one approach, R 33' It is a hydroxyl group.

[0172] In another way, R 33' The organic group is monovalent, preferably C. 1－20 Alkyl, more preferably C 1－6 alkyl.

[0173] The aforementioned q2' are each an independent integer from 0 to 3, and the aforementioned r2' are each an independent integer from 0 to 3. Furthermore, the sum of q2' and r2' is within (CR... 32' q2' R 33' r2' The value in unit ) is 3.

[0174] q2' in each (CR 32' q2' R 33' r2' The units are preferably integers of 1 to 3, more preferably 2 to 3, and even more preferably 3.

[0175] R 32 Each independently is -Z 3 -SiR 34 n2 R 35 3－n2 The -Z 3 -SiR 34 n2 R 35 3－n2 The meaning of R above is the same as above. 32' The records are the same.

[0176] R 33 Each of these can be an organic group that is independently a hydrogen atom, a hydroxyl group, or a monovalent organic group. Such a monovalent organic group is a monovalent organic group other than the hydrolyzable groups mentioned above.

[0177] In R 33 In this context, the monovalent organic group is preferably C. 1－20 Alkyl or -(C s H2s ) t1 -(O-C s H 2s ) t2 -H (where s is an integer from 1 to 6, preferably an integer from 2 to 4, t1 is 1 or 0, preferably 0, t2 is an integer from 1 to 20, preferably an integer from 2 to 10, more preferably an integer from 2 to 6), more preferably C 1－20 Alkyl, more preferably C 1－6 Alkyl groups, particularly preferably methyl groups.

[0178] In one approach, R 33 It is a hydroxyl group.

[0179] In another way, R 33 The organic group is monovalent, preferably C. 1－20 Alkyl, more preferably C 1－6 alkyl.

[0180] p2, q2, and r2 are all independent integers from 0 to 3. Furthermore, the sum of p2, q2, and r2 is within (CR...). 31 p2 R 32 q2 R 33 r2 The value in unit ) is 3.

[0181] In one mode, p2 is 0.

[0182] In one approach, p2 is in each (CR) 31 p2 R 32 q2 R 33 r2 Each of the units is an integer from 1 to 3, an integer from 2 to 3, or 3. In the preferred embodiment, p2 is 3.

[0183] In one approach, q2 is in each (CR) 31 p2 R 32 q2 R 33 r2 Each of the units is an integer from 1 to 3, preferably an integer from 2 to 3, and more preferably 3.

[0184] In one mode, p2 is 0, and q2 is in each (CR) 31 p2 R 32 q2 R 33 r2Each of the units is an integer from 1 to 3, preferably an integer from 2 to 3, and more preferably 3.

[0185] The above R e1 Each independently is -Z 3 -SiR 34 n2 R 35 3－n2 The -Z 3 -SiR 34 n2 R 35 3－n2 The meaning of R above is the same as above. 32' The records are the same.

[0186] The above R f1 Each of these can be an organic group that is independently a hydrogen atom, a hydroxyl group, or a monovalent organic group. Such a monovalent organic group is a monovalent organic group other than the hydrolyzable groups mentioned above.

[0187] In the above R f1 In this context, the monovalent organic group is preferably C. 1－20 Alkyl or -(C s H 2s ) t1 -(O-C s H 2s ) t2 -H (where s is an integer from 1 to 6, preferably an integer from 2 to 4, t1 is 1 or 0, preferably 0, t2 is an integer from 1 to 20, preferably an integer from 2 to 10, more preferably an integer from 2 to 6), more preferably C 1－20 Alkyl, more preferably C 1－6 Alkyl groups, particularly preferably methyl groups.

[0188] In one approach, R f1 It is a hydroxyl group.

[0189] In another way, R f1 The organic group is monovalent, preferably C. 1－20 Alkyl, more preferably C 1－6 alkyl.

[0190] In the above examples, k2, l2, and m2 are all independent integers from 0 to 3. The sum of k2, l2, and m2 is within the range (CR). d1 k2 R e1 l2 R f1 m2 The value in unit ) is 3.

[0191] In one embodiment, at each end portion of formula (S4), there are two or more, for example, 2 to 27, preferably 2 to 9, more preferably 2 to 6, further preferably 2 to 3, particularly preferably 3, n2 is 1 to 3, preferably 2 or 3, more preferably 3 (SiR). 34 n2 R 35 3－n2 )unit.

[0192] In the preferred embodiment, R exists in equation (S4). 32' At that time, in at least one, preferably all of R 32' In this context, n2 is an integer from 1 to 3, preferably 2 or 3, and more preferably 3.

[0193] In the preferred embodiment, R exists in equation (S4). 32 At that time, in at least one, preferably all of R 32 In this context, n2 is an integer from 1 to 3, preferably 2 or 3, and more preferably 3.

[0194] In the preferred embodiment, R exists in equation (S4). e1 At that time, in at least one, preferably all of R a1 In this context, n2 is an integer from 1 to 3, preferably 2 or 3, and more preferably 3.

[0195] In the preferred embodiment, in formula (S4), k2 is 0, l2 is 2 or 3, preferably 3, and n2 is 2 or 3, preferably 3.

[0196] The above R g1 and R h1 Each independently is -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 Among them, R 11 R 12 R a1 R b2 R c1 R d1 R e1 R f1The meanings of n1, k1, l1, m1, k2, l2, and m2 are the same as above.

[0197] In the preferred embodiment, R g1 and R h1 Each independently is -Z 4 -SiR 11 n1 R 12 3－n1 .

[0198] The above Z 4 Each of these can be an organic group that is independently a single bond, an oxygen atom, or a divalent organic group. Furthermore, it will be hereinafter denoted as Z. 4 The right side of the structure and (SiR) 11 n1 R 12 3－n1 ) bond.

[0199] In one approach, Z 4 It is an oxygen atom.

[0200] In one approach, Z 4 It is a divalent organic group.

[0201] In the preferred method, Z 4 It does not contain siloxane bonds.

[0202] The above Z 4 C is preferred 1－6 Alkylene, -(CH2) z5'' -O-(CH2) z6'' - (where z5'' is an integer from 0 to 6, for example, an integer from 1 to 6, and z6'' is an integer from 0 to 6, for example, an integer from 1 to 6) or - (CH2) z7'' -Phenylidene-(CH2) z8'' —(In the formula, z7'' is an integer from 0 to 6, for example, an integer from 1 to 6; z8'' is an integer from 0 to 6, for example, an integer from 1 to 6). Such a C 1－6 The alkylene group can be straight-chain or branched, preferably straight-chain. These groups can be selected from, for example, fluorine atoms, C atoms, etc. 1－6 Alkyl, C 2－6 alkenyl and C 2－6 One or more substituents in the alkynyl group are substituted, but preferably unsubstituted.

[0203] In the preferred method, Z 4 C 1－6 Alkylene or -(CH2) z7'' -Phenylidene-(CH2) z8'' -, preferably -phenylene-(CH2) z8'' -. Z4 When such a group is present, light tolerance, especially UV tolerance, is further improved.

[0204] In another preferred embodiment, the aforementioned Z 4 C 1－3 Alkylene. In one manner, Z 4 It can be -CH2CH2CH2-. In another way, Z 4 It can be -CH2CH2-.

[0205] In a preferred embodiment, formulas (S1), (S2), (S3), (S4), and (S5) do not contain siloxane bonds.

[0206] In one approach, R Si It is a group represented by formula (S3), (S4) or (S5).

[0207] In one approach, R Si It is a group represented by formula (S3) or (S4).

[0208] In one approach, R Si It is a group represented by formula (S4) or (S5).

[0209] In one approach, R Si The group is represented by formula (S1). In a preferred embodiment, formula (S1) is represented by formula (S1-b). In a preferred embodiment, R is a group represented by formula (S1-b). 13 X is a hydrogen atom. 11 For single bond or -R 28 -O x -R 29 - (where R is the formula) 28 and R 29 Each independently is a single bond or C 1－20 Alkylene (x is 0 or 1), n1 is 1 to 3, preferably 2 to 3, and more preferably 3.

[0210] In one approach, R Si The group is represented by formula (S2). In a preferred embodiment, formula (S2) is -SiR. 11 2R 12 or -SiR 11 3.

[0211] In one approach, R Si The group is represented by formula (S3). In a preferred embodiment, formula (S3) is -SiR. a1 2R c1 or -SiR a1 3, R a1 -Z 1 -SiR22 q1 R 23 r1 Z 1 C 1－6 Alkylene, -(CH2) z1 -O-(CH2) z2 - (where z1 is an integer from 0 to 6, for example, an integer from 1 to 6, and z2 is an integer from 0 to 6, for example, an integer from 1 to 6) or - (CH2) z3 -Phenylidene-(CH2) z4 —(where z3 is an integer from 0 to 6, for example, an integer from 1 to 6, and z4 is an integer from 0 to 6, for example, an integer from 1 to 6), preferably C 1－6 Alkylene, q1 is 1 to 3, preferably 2 to 3, and more preferably 3.

[0212] In one approach, R Si The group is 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 Z 3 C 1－6 Alkylene, -(CH2) z5'' -O-(CH2) z6'' - (where z5'' is an integer from 0 to 6, for example, an integer from 1 to 6, and z6'' is an integer from 0 to 6, for example, an integer from 1 to 6) or - (CH2) z7'' -Phenylidene-(CH2) z8'' — (where z7'' is an integer from 0 to 6, for example, an integer from 1 to 6, and z8'' is an integer from 0 to 6, for example, an integer from 1 to 6), preferably C 1－6 Alkylene, n2 is 1 to 3, preferably 2 to 3, and more preferably 3.

[0213] In one approach, R Si The group is represented by formula (S5). In a preferred embodiment, R g1 and R h1 -Z 4 -SiR 11 n1 R 12 3－n1 Z 4 C 1－6 Alkylene, -(CH2) z5'' -O-(CH2)z6'' - (where z5'' is an integer from 0 to 6, for example, an integer from 1 to 6, and z6'' is an integer from 0 to 6, for example, an integer from 1 to 6) or - (CH2) z7'' -Phenylidene-(CH2) z8'' — (where z7'' is an integer from 0 to 6, for example, an integer from 1 to 6, and z8'' is an integer from 0 to 6, for example, an integer from 1 to 6), preferably C 1－6 Alkylene, n1 is 1 to 3, preferably 2 to 3, and more preferably 3.

[0214] m is an integer from 1 to 100, preferably from 5 to 80, more preferably from 10 to 50, for example, it can be an integer from 20 to 50 or from 20 to 40.

[0215] n is an integer from 1 to 50, preferably from 1 to 20, more preferably from 1 to 10, and for example, it can be an integer from 2 to 10.

[0216] o is an integer from 0 to 200, preferably 5 to 100, more preferably 10 to 80, and even more preferably 15 to 50. For example, it can be an integer from 20 to 50, 20 to 40, or 30 to 50.

[0217] The fluorosilicone compound shown in formula (I) above can have 1×10 2 ~1×10 6 The number average molecular weight is not particularly limited. The fluorosilicone compound represented by formula (I) above preferably has a number average molecular weight of 1,000 to 100,000, more preferably 2,000 to 50,000. This "number average molecular weight" is determined using GPC.

[0218] Fluorosilicones of formula (I) are obtained, for example, by reacting a Si-H-containing compound of formula (II) with: R A -X''-CH=CH2 or R Si -Y'-CH=CH2 [where X'' and Y' are divalent groups, preferably divalent groups or bonds having 1 to 18 carbon atoms, R] A and R Si The meaning is the same as that of the compound described in formula (I) above. The compound is prepared by an addition reaction in the presence of a catalyst for the hydrosilylation reaction. [In this formula, the meanings of each symbol are the same as those in formula (I).] The present invention provides a release composition comprising a fluorosilicone compound of formula (I) of the present invention. The release composition may be a single product or a mixture of at least two products.

[0219] The fluorosilicone release composition of the present invention may contain a curing-promoting catalyst. This catalyst promotes the dehydration condensation reaction of the silanol groups. Examples of curing-promoting catalysts include (preferably) organometallic salts having 1 to 30 carbon atoms, such as dibutyltin dilaurate, dibutyltin diacetate, tetrabutyl titanate (butoxytitanium), tetraisopropyl titanate (isopropoxytitanium), bis(acetylacetonyl)diisopropyl titanate, bis(ethyl acetoacetate)diisopropyl titanate {bis(ethyl acetoacetate)diisopropoxytitanium}, and other chelates of titanium and zirconium disclosed in WO2001-49774 (the invention is cited in this application), acids (particularly organic acids having 1 to 10 carbon atoms), such as acetic acid or propionic acid, and carboxylates.

[0220] Based on 100 parts by weight of fluorosilicone compound, the amount of curing-promoting catalyst added is usually at most 20 parts by weight, preferably 0.05 to 10 parts by weight.

[0221] The fluorosilicone release composition of the present invention 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 then evaporates, causing the fluorosilicone release agent to accumulate. Examples of solvents include: aliphatic solvents such as hexane, cyclohexane, heptane, octane, isooctane, and industrial gasoline; aromatic solvents such as benzene, toluene, and xylene; ester solvents such as ethyl acetate and butyl acetate; alcohol solvents such as isopropanol and ethanol; chlorinated solvents such as trichloroethylene, chloroform, and hexachlorom-xylene; ketone solvents such as acetone and methyl ethyl ketone; ether solvents such as diethyl ether, diisopropyl ether, and tetrahydrofuran; fluorinated solvents such as HCFC-225, HFC-365, methyl perfluorobutyl ether, and ethyl perfluorobutyl ether; and low-boiling-point (maximum 150°C) silicone solvents such as hexamethyldisiloxane and heptamethyltrisiloxane.

[0222] The fluorosilicone release composition of the present invention can be in the form of an aerosol formed by filling a solution of a fluorosilicone compound together with a propellant such as LPG.

[0223] The fluorosilicone release composition of the present invention can also be a solution containing fluorosilicone compounds and organic solvents, or an aqueous emulsion containing fluorosilicone compounds and water.

[0224] When the release composition is an aqueous emulsion, it is preferable to contain at least one emulsifier selected from nonionic emulsifiers, anionic emulsifiers and cationic emulsifiers as the emulsifier.

[0225] As a nonionic emulsifier, any substance capable of emulsifying and dispersing the fluoropolymer of the present invention in an aqueous emulsion is acceptable, such as polyoxyethylene alkyl ethers, sorbitol alkylates, and sorbitol alkyl esters. Examples of polyoxyethylene alkyl ethers include polyoxyethylene lauryl ether.

[0226] Examples of anionic emulsifiers include alkyl sulfates, alkyl sulfonates, and alkyl phosphates. Examples of alkyl sulfates include sodium alkyl sulfate.

[0227] Examples of cationic emulsifiers include quaternary ammonium salts and alkylamine salts. Examples of quaternary ammonium salts include lauryltrimethylammonium chloride.

[0228] The amount of emulsifier is typically 0.5 to 25 parts by weight relative to 100 parts by weight of the fluoropolymer, preferably 1.0 to 20 parts by weight, and more preferably 2.0 to 15 parts by weight.

[0229] The fluorosilicone release composition of the present invention can be applied using well-known methods. For example, the mold can be immersed in a diluent of the release composition, sprayed with the diluent, or brushed with the diluent, and then the solvent can be evaporated to remove it. Afterward, the mold is heated, causing hydrolysis and partial condensation with the silane groups to form a cured film, thereby improving durability. Heating is preferably performed at 50–200°C for about 10–60 minutes.

[0230] The fluorosilicone release composition of the present invention can be used in combination with other release ingredients. Examples of other release ingredients 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; fluorinated oils such as CTFE oil and PFPE oil; and fluorinated resins such as PTFE and PCTFE. Based on 100 parts by weight of fluorosilicone compound (I), the amount of other release ingredients can be from 1 part by weight to 1000 parts by weight.

[0231] When the release composition is an aerosol, a propellant can be used to fill the aerosol can. Examples of propellants include LPG, dimethyl ether, and carbon dioxide. The amount of propellant is typically 10–95% by weight, preferably 20–90% by weight, and more preferably 30–90% by weight, relative to the total amount of the release composition and the propellant. When the amount of propellant is 10% by weight or more, better spraying is possible, and a more uniform coating is likely to be obtained. Furthermore, when the amount of propellant is 95% by weight or less, the coating does not become too thin, and the release properties do not decrease excessively.

[0232] The release composition can be used as an internal or external release agent, preferably as an external release agent.

[0233] The release composition is typically used as described below. The release composition is applied to the inner surface of the molding die, and after the solvent and dispersant have dried and been removed, a release agent coating (a fluoropolymer coating) is formed on the molding die. The molding composition is then filled into the mold to form the molding material, which is then removed from the mold.

[0234] That is, the present invention also provides a method for forming the above-mentioned coating. For example, the coating forming method of the present invention includes: (i) a step of coating the release composition of the present invention onto the inner surface of a molding die to form a coating of the release composition.

[0235] The present invention also provides a method for manufacturing a molded article using the release composition of the present invention. For example, the method for manufacturing a molded article of the present invention includes: (i) The process of coating the release composition of the present invention onto the inner surface of the molding die to form a film of the release composition; (ii) The process of filling a molding composition into a molded mold having a release composition to obtain a molded article; and (iii) The process of removing the molded part from the molding die.

[0236] Examples of molds used as release dies include metal molds made of aluminum, SUS, iron, etc., epoxy resin and wood molds, and molds that have been electroformed with nickel or plated with chromium.

[0237] Examples of molding materials that can be demolded using a release composition include: polyurethane rubber, H-NBR, NBR, silicone rubber, EPDM, CR, NR, fluororubber, SBR, BR, IIR and IR, etc.; or thermosetting resins such as polyurethane foam, epoxy resin, phenolic resin and FRP (e.g. CFRP and GFRP), thermoplastic resins such as ABS, polycarbonate and PBT, etc.

[0238] The present invention provides a coating obtained from a release composition containing a fluorosilicone compound of formula (I) of the present invention.

[0239] In this invention, examples of raw materials used for the demolded molded articles include polyurethane, butyl rubber, styrene-butadiene rubber, chloroprene rubber, EPDM, NBR, ACM, polyurethane rubber, silicone rubber, fluororubber, polycarbonate, epoxy resin, phenolic resin, unsaturated polyester, melamine, FRP, PVC, ABS, EVA, and PP.

[0240] Applications of the present invention include gaskets, O-rings, sealing gaskets, belts, panels, and hoses.

[0241] The compounds and release compositions of the present invention have been described in detail above, but the compounds and release compositions of the present invention are not limited to the examples described above.

[0242] Example The fluorosilicone compounds and release compositions of the present invention are described below using examples, but the present invention is not limited to the following examples. In these examples, the order of the repeating units constituting the siloxane moiety is arbitrary, and the chemical formulas shown below represent the average composition.

[0243] Synthesis example 1 A stirrer, thermometer / temperature controller, and dropping funnel were installed on a 100 ml three-necked round-bottom flask. THF (45 g), 4-trifluoromethoxyphenol (5.1 g), and potassium carbonate (8.3 g) were added. Then, after adding allyl bromide (10.8 g), the mixture was stirred at room temperature for 4 hours to allow the reaction to proceed. Finally, purification was performed to obtain CF3O(C6H4)OCH2CHCH2 (compound 1). Synthesis example 2 A stirrer, thermometer / temperature controller, hood heater, water-cooled reflux cooler with CaSO4-filled drying tube, and dropping funnel are installed on a 250 ml four-necked round-bottom flask.

[0244] Add Me3SiO-(Me2SiO) to the flask n —(MeHSiO) m 2.0 g of a siloxane with the structure -SiMe3 (Me is methyl, n is 38, m is 36) was heated to 60 °C. Then, CF3O(C6H4)OCH2CHCH2 (compound 1, 2.24 g) containing Pt (17 mg) that forms a complex with 1,2-divinyltetramethyldisiloxane was added. Next, 0.4 g of vinyltrimethoxysilane was added dropwise. The mixture was then heated under vacuum to remove excess olefins. Finally, filtration was performed to obtain compound 2.

[0245] Synthesis example 3 Except that 2.51 g of CF3O(C6H4)OCH2CHCH2 (compound 1) was used, compound 3 was prepared by the same procedure as in synthesis example 2.

[0246] Synthesis example 4 Compound 4 was prepared by the same procedure as in Synthesis Example 2, except that 2.67 g of CF3O(C6H4)OCH2CHCH2 (compound 1) and 0.2 g of vinyltrimethoxysilane were used. Compound 2: x = 29, y = 7, z = 38 Compound 3: x = 32, y = 4, z = 38 Compound 4: x = 34, y = 2, z = 38 As control compounds, the following control compounds 1-2 are prepared.

[0247] Control compound 1: x = 36, y = 0, z = 38 Control compound 2: x = 0, y = 36, z = 38 Example Demolding tests were conducted using compounds 2-4, control compounds 1-2, a compound synthesized according to the method described in Synthesis Example 1 of Japanese Patent No. 5184382 (control compound 3), and a commercially available mold release agent (DAIFREE GF-700, manufactured by Daikin Industries, Ltd.) (control compound 4).

[0248] (evaluate) "Demolding test" The release composition was diluted with isohexane to a solid content of 0.5% by mass, and this solution was sprayed onto an aluminum plate measuring 9.5cm × 9.5 × 0.15cm. The plate was then dried at 150°C for 15 minutes, leaving a residue of 0.2–0.3 mg / cm² on the metal surface. 2 The non-volatile components were then analyzed. Next, perforated tape was applied to an aluminum plate. Then, a 3.0cm x 3.0cm piece of CFRP prepreg (3K plain woven carbon, manufactured by Nippon Composite Materials Co., Ltd.) was applied to a coated plate, and the aluminum plate was placed over it to create a molded test sample. The test sample was clamped in a press and cured at 10MPa pressure while being heated at 150°C for 10 minutes. After the test sample cooled, the covering aluminum plate was removed, and the test sample was mounted on a push-pull force gauge. The clamp of the push-pull force gauge was installed in the hole of the tape in the test sample, and the tape was pulled at a constant rate to demold the molded CFRP prepreg from the coated plate. The force required for lifting was measured as the demolding force. Furthermore, the same tool was used to continuously demold articles, and the number of consecutive demoldings that could no longer be demolded (i.e., demolding times) was measured.

[0249] "Non-transferability evaluation" The demolded surface of the CFRP prepreg after the demolding test was observed using a SEM (JCM-7000, manufactured by JEOL). The composition of the release agent on the surface was determined by SEM-EDX, and their amounts were compared. The less the composition of the release agent, the better the non-transferability. The comparison results are classified as follows.

[0250] ○: There is almost no residue from the release agent (excellent non-transferability). △: There is some residue from the release agent, but very little (not good transferability). ×: There is residual component from the release agent, and the amount is large (poor non-transferability). "Evaluation of Coating Adhesion" An acrylic polyurethane coating (NYPORIN K, manufactured by Shendong Coatings Co., Ltd.) was applied to the demolded surface of the CFRP prepreg after the demolding test using a spray gun and dried at room temperature for 12 hours. Then, the adhesion between the coating and the prepreg was evaluated using a cross-cutting test according to JIS K5600. Specifically, a 5×5 grid was formed on the coating with each square measuring 2 mm longitudinally and 2 mm laterally using a cutter. CELLOTAPE (registered trademark) was then affixed to the gridded coating and peeled off by pressing with a finger. The coating residue rate was calculated based on the grid remaining on the prepreg, and the results are categorized as follows.

[0251] ◎: The coating residue rate is over 80% (excellent adhesion). ○: The coating residue rate is over 60-80% (good non-transferability). △: The coating residue rate is 20-60% or more (poor non-transferability). ×: Coating residue rate is less than 20% (very poor non-transferability). Table 1 Based on the above results, the fluorosilicone compounds of the present invention exhibit good mold release and non-transfer properties. In contrast, the compounds of the comparative examples did not exhibit any effect on mold release or non-transfer properties.

[0252] Industrial availability The fluorosilicone compounds of the present invention can be effectively used as mold release agents.

Claims

1. A fluoro-silicone compound represented by the formula (I) : ###0001### wherein X and Y are each independently a divalent organic group, m is an integer of 1 to 100, n is an integer of 1 to 50, o is an integer of 0 to 200, and the order of presence of each repeating unit marked with m, n and o in parentheses is arbitrary.

2. The fluoro-silicone compound according to claim 1, wherein: ###0002### R A CF3-, CF3O-, CF3NH-, CF3CH2NH-, (CF3)2N-, (CF3CH2)2N-, CF3S-, CF3C(=0)-, CF3CH2C(=0)-, CF3C(=0)0-, CF3CH2OC(=0)-, CF3CONH-, CF3CH2CONH-, 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 substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, R 3 and R 10 are each independently substituted or unsubstituted alkyl, substituted or unsubstituted aryl, R A -X-, or R Si -Y-, 3. The fluoro-silicone compound according to claim 1 or 2, wherein: ###0003### R Si R is a monovalent radical comprising a Si atom to which a hydroxyl group or a hydrolyzable group is bonded, 4. The fluoro-silicone compound according to any one of claims 1 to 3, wherein: ###0004### 5. The fluoro-silicone compound according to any one of claims 1 to 4, wherein: ###0005### wherein a1 is an integer of 0 to 10, b1 is an integer of 0 to 200, c1 is an integer of 0 to 200, and d1 is an integer of 0 to 10, and the order of presence of each repeating unit marked with the symbols a1, b1, c1 and d1 in parentheses is arbitrary.

6. The fluoro-silicone compound according to any one of claims 1 to 5, wherein: ###0006### wherein a1 is 0 or 1, c1 is an integer of 1 to 36, and d1 is 0 or 1.

7. The fluoro-silicone compound according to any one of claims 1 to 6, wherein: Y is an alkylene group or an alkyloxyalkylene group.

8. The fluoro-silicone compound according to any one of claims 1 to 7, wherein: ###0007### in the formulae (SI), (S2), (S3), (S4) and (S5), t are each independently an integer of 2 or more, pi are each independently an integer of 0 to 3, qi are each independently an integer of 0 to 3, ri are each independently an integer of 0 to 3, pi' are each independently an integer of 0 to 3, qi' are each independently an integer of 0 to 3, ri' are each independently an integer of 0 to 3, qi" are each independently an integer of 0 to 3, ri" are each independently an integer of 0 to 3, ki are each independently an integer of 0 to 3, li are each independently an integer of 0 to 3, mi are each independently an integer of 0 to 3, p2 are each independently an integer of 0 to 3, q2 are each independently an integer of 0 to 3, r2 are each independently an integer of 0 to 3, q2' are each independently an integer of 0 to 3, r2' are each independently an integer of 0 to 3, n2 are each independently an integer of 0 to 3, k2 are each independently an integer of 0 to 3, l2 are each independently an integer of 0 to 3, m2 are each independently an integer of 0 to 3, k3 is 1 or 2, and l3 is 0 or 1, and wherein in the formula (SI), (S2), (S3), (S4) or (S5), there are at least 2 Si atoms to which a hydroxyl group or a hydrolyzable group is bonded. R A CF3O", CF3NH" or (CF3)2N".

9. A mold release composition, characterized by: ###0008### containing the fluoro-silicone compound according to any one of claims 1 to 8. R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are each independently C 1－4 alkyl.

10. The mold release composition according to claim 9, characterized by: ###0009### further containing a liquid medium selected from at least one of water and an organic solvent. R 3 and R 10 are each independently C 1－4 alkyl.

11. The mold release composition according to claim 9 or 10, characterized by: ###0010### being a solution or an aerosol containing an organic solvent, or an aqueous emulsion containing water. X is -(Ar) a1 -(CH2) b1 -(CH2) c1 -(O) d1 -(CH2) ​ Ar is a divalent aromatic group which can be substituted by a fluorine atom or R A substituted by a fluorine atom or R ​ ​ ​ ​ ​ ​ X is -(Ar) a1 -(O) d1 -(CH2) c1 groups shown below, ​ Ar is a divalent aromatic group which can be substituted by a fluorine atom or R A a divalent aromatic group which can be substituted by a fluorine atom or R ​ ​ ​ ​ ​ ​ R Si a group represented by the following formula (S1), (S2), (S3), (S4) or (S5), ​ R 11 are each independently hydroxyl or a hydrolyzable group, R 12 each independently is a monovalent organic radical, n1 is an integer of 0 to 3 in each (SiR 11 n1 R 12 3－n1 ) unit is independently 0 to 3. X 11 are each independently a single bond or a divalent organic group, R 13 each independently is a hydrogen atom or a monovalent organic group, ​ R 14 each independently is a hydrogen atom, a halogen atom or -X 11 -SiR 11 n1 R 12 3－n1 , R 15 each independently is 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 -Z 1 -SiR 21 p1 R 22 q1 R 23 r1 , Z 1 each independently is a divalent organic radical, R 21 each independently -Z 1' -SiR 21' p1' R 22' q1' R 23' r1' , R 22 are each independently hydroxyl or a hydrolyzable group, R 23 each independently is a monovalent organic radical, ​ ​ ​ Z 1' each independently is a divalent organic radical, R 21' are each independently -Z 1'' -SiR 22'' q1'' R 23'' r1'' , R 22' are each independently hydroxyl or a hydrolyzable group, R 23' are each independently a monovalent organic radical, ​ ​ ​ Z 1'' each independently is a divalent organic radical, R 22'' are each independently hydroxyl or a hydrolyzable group, R 23'' each independently is a monovalent organic radical, ​ ​ R b1 are each independently hydroxyl or a hydrolyzable group, R c1 each independently is a monovalent organic radical, ​ ​ ​ R d1 each independently -Z 2 -CR 31 p2 R 32 q2 R 33 r2 , Z 2 are each independently a single bond, an oxygen atom, or a divalent organic group, R 31 are each independently -Z 2' -CR 32' q2' R 33' r2' , R 32 are each independently -Z 3 -SiR 34 n2 R 35 3－n2 , R 33 each independently is a hydrogen atom, a hydroxyl group, or a monovalent organic group, ​ ​ ​ Z 2' are each independently a single bond, an oxygen atom, or a divalent organic group, R 32' are each independently -Z 3 -SiR 34 n2 R 35 3－n2 , R 33' each independently is a hydrogen atom, a hydroxyl group, or a monovalent organic group, ​ ​ Z 3 are each independently a single bond, an oxygen atom, or a divalent organic group, R 34 are each independently hydroxyl or a hydrolyzable group, R 35 each independently is a monovalent organic radical, ​ R e1 are each independently -Z 3 -SiR 34 n2 R 35 3－n2 , R f1 each independently is a hydrogen atom, a hydroxyl group, or a monovalent organic group, ​ ​ ​ R g1 and R h1 are each independently -Z 4 -SiR 11 n1 R 12 3－n1 , -Z 4 -SiR a1 k1 R b1 l1 R c1 m1 or -Z 4 -CR d1 k2 R e1 l2 R f1 m2 , Z 4 are each independently a single bond, an oxygen atom, or a divalent organic group, ​ ​ ​ ​ ​ ​ ​ ​ ​ 12. The mold release composition according to any one of claims 9 to 11, wherein: 0.05 parts by weight to 10 parts by weight relative to 100 parts by weight of the fluoro silicone compound (I).

13. The mold release composition according to any one of claims 9 to 12, wherein: 0.1 parts by weight to 99 parts by weight relative to 100 parts of the fluoro silicone compound (I).

14. A film, wherein: The film is obtained from the mold release composition according to any one of claims 9 to 13.

15. A method for forming a release agent film, characterized by including: (i) a step of applying the mold release composition according to any one of claims 9 to 13 to the inner surface of a molding die to form a film of the mold release composition.

16. A method for producing a molded body, characterized by including: (i) a step of applying the mold release composition according to any one of claims 9 to 13 to the inner surface of a molding die to form a film of the mold release composition; (ii) a step of filling a molding composition into the molding die having the film of the mold release composition to obtain a molded body; and (iii) a step of taking out the molded body from the molding die.

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