Polyorganosiloxane

Abstract

The present invention provides a polyorganosiloxane contained in a mold release agent that exhibits better release properties from resins and the like. [Solution] A polyorganosiloxane represented by formula (11) or formula (12). Each reference numeral is as described in the specification. TIFF2026083361000060.tif66138

Description

[Technical Field]

[0001] This disclosure relates to polyorganosiloxanes. [Background technology]

[0002] When molding synthetic resins, rubber, etc., a release agent is applied to the inner surface of the mold (die) in advance to improve the release properties between the molded synthetic resin, etc. and the mold (for example, Patent Document 1). [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Japanese Patent Publication No. 2011-121367 [Overview of the project] [Problems that the invention aims to solve]

[0004] The present disclosure aims to provide a polyorganosiloxane contained in a mold release agent that exhibits better release properties from resins and the like, and also good adhesion to molds. [Means for solving the problem]

[0005] This disclosure provides the following [1] to

[28] . [1] Formula (11): [ka] [In formula: R 1 Each of these is independently a hydrogen atom or a monovalent organic group; R 2 Each of these is independently a hydrogen atom or a monovalent organic group; R 4 Each of these is independently a hydrogen atom or a monovalent organic group; R 5is, independently of each other, a hydrogen atom or a monovalent organic group; R 6 is, independently of each other, a hydrogen atom or a monovalent organic group; R Si is, independently of each other, -(O-SiR 7 2) m -OSiR 1 2R 2 ; [[ID=-18]]R 7 [[ID=-20]]is, independently of each other, a monovalent organic group or R Si’ ; R Si’ is synonymous with R Si ;[[ID=-29]] m is an integer of 0 or more; However, at least one of R 1 R 2 R 4 R 5 R 6 and R 7 is a group represented by formula (2):

Chemical formula

Chemical formula

化

Chemical formula

Chemical formula

[10] Y 1 The polyorganosiloxane described in any one of [1] to [9], which does not contain esters, secondary amines, amides, ethers, thioethers, or thioesters.

[11] Y 1 The polyorganosiloxane described in any one of [1] to

[10] , which does not contain a group represented by -CH2-N=CH-.

[12] Y 1 C 1-20 A polyorganosiloxane described in any one of [1] to

[10] , which is an alkylene group.

[13] n1 is 3 or greater, and is a polyorganosiloxane as described in any one of [1] to

[12] .

[14] A polyorganosiloxane according to any one of [1] to

[13] , which does not contain a fluorine atom.

[15] A polyorganosiloxane described in any of the following [1] to

[14] . JPEG2026083361000008.jpg2577[In the formula, n is 34.] JPEG2026083361000009.jpg2486 [In the formula, n=34.] JPEG2026083361000010.jpg4769 [In the equation, x=27, y=2, and z=1.]

[16] A composition comprising a polyorganosiloxane described in any one of [1] to

[15] .

[17] The composition according to

[16] , further comprising a solvent.

[18] The solvent is an organic solvent, as described in

[17] .

[19] The solvent is an aqueous medium, the composition as described in

[17] .

[20] Furthermore, the composition according to any one of

[16] to

[20] , comprising an emulsifier. [twenty one] Furthermore, the composition according to

[20] further comprises an aqueous medium. [twenty two] Furthermore, the composition according to

[16] , further comprising an additive. [twenty three] A composition according to any one of

[16] to

[22] , comprising a catalyst, a crosslinking agent, a thickening agent, or a pH adjuster. [twenty four] Furthermore, the composition according to

[23] further comprises an organic solvent. [twenty five] Furthermore, the composition according to

[23] further comprises an aqueous medium.

[26] A composition according to any one of

[16] to

[25] , which is a mold release agent or a water-repellent and oil-repellent agent.

[27] A molding method for processing a molding material using a mold, A molding method wherein the mold is surface-treated with the composition described in any one of

[16] to

[26] .

[28] The molding material is a thermosetting resin, as described in

[27] .

[29] The molding method according to

[28] , wherein the thermosetting resin is a carbon fiber composite material. [Effects of the Invention]

[0006] According to this disclosure, it is possible to provide a polyorganosiloxane contained in a mold release agent that exhibits better release properties from resins and the like, and good adhesion to molds. [Modes for carrying out the invention]

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

[0008] As used herein, "hydrocarbon group" means a group containing carbon and hydrogen, from which one hydrogen atom has been removed from the molecule. Such hydrocarbon groups are not particularly limited, but include hydrocarbon groups having 1 to 20 carbon atoms, which may be substituted with one or more substituents, such as aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The above-mentioned "aliphatic hydrocarbon group" may be linear, branched, or cyclic, and may be saturated or unsaturated. Furthermore, the hydrocarbon group may contain one or more ring structures.

[0009] In the use herein, the substituents of the "hydrocarbon group" are not particularly limited, but include, for example, halogen atoms; C, which may be substituted with one or more halogen atoms. 1-6 Alkyl alkyl group, C 2-6 Alkenyl group, C 2-6 Alkynyl group, C 3-10 Cycloalkyl groups, C 3-10Unsaturated cycloalkyl group, 5-10 membered heterocyclyl group, 5-10 membered unsaturated heterocyclyl group, C 6-10 Examples include one or more groups selected from aryl groups and 5- to 10-membered heteroaryl groups.

[0010] In this specification, alkyl groups and phenyl groups may be unsubstituted or substituted. Substituents for such groups are not particularly limited, but include, for example, halogen atoms and C 1-6 Alkyl alkyl group, C 2-6 Alkenyl group and C 2-6 One or more groups selected from alkynyl groups are examples.

[0011] [Polyorganosiloxane] The polyorganosiloxanes of this disclosure are given by the following formula (11): [ka] or Formula (12) below: [ka] It is represented as follows.

[0012] In equation (11), R 1 Each of these is independently a hydrogen atom or a monovalent organic group; R 2 Each of these is independently a hydrogen atom or a monovalent organic group; R 4 Each of these is independently a hydrogen atom or a monovalent organic group; R 5 Each of these is independently a hydrogen atom or a monovalent organic group; R 6 Each of these is independently a hydrogen atom or a monovalent organic group; R Si These are, independently, -(O-SiR 7 2) m -OSiR 1 2R 2 and; R 7 Each of these is independently a monovalent organic group or R Si’ and; R Si’ R Si It is synonymous with; m is a non-negative integer; However, R 1 , R 2 , R 4 , R 5 , R 6 and R 7 At least one of them is equation (2): [ka] It is a base represented by; X 1 is a hydrogen atom or a protecting group; Y 1 These are single bonds or 2-10 valent organic groups; n1 is an integer greater than or equal to 2; a is a non-negative integer; b is a non-negative integer; c is a non-negative integer; The sum of a, b, and c is an integer greater than or equal to 2; The order in which the repeating units labeled a, b, and c are enclosed in parentheses is arbitrary within the expression.

[0013] In equation (12), R 4 Each of these is independently a hydrogen atom or a monovalent organic group; R 5 Each of these is independently a hydrogen atom or a monovalent organic group; However, R 4 and R 5 At least one of them is equation (2): [ka] It is a base represented by; X 1 is a hydrogen atom or a protecting group; Y 1is a single bond or an organic group having a valence of 2 to 10; n1 is an integer of 2 or more; d is an integer of 1 or more.

[0014] The above compound can be provided on a substrate to form a surface treatment layer (cured layer), and a resin such as a carbon fiber composite material can be provided on the surface treatment layer for use. X 1 When X is a hydrogen atom, it is considered that the oxygen atom of the group represented by the formula (2) interacts with the surface portion (for example, metal) of the substrate. On the other hand, since the -Si-O- group in the formula (11) or the formula (12) has water repellency, the bonding strength with the resin is not very good. Thus, the above compound can function as a release agent that suppresses the bonding property between the substrate and the resin. Furthermore, due to the good adhesiveness to the substrate, it can adhere to the substrate and function as a release agent that suppresses the bonding property between the substrate and the resin. Incidentally, when X 1 is a protecting group, since the protecting group is a group that protects a hydroxyl group, the surface treatment layer is formed after removing the protecting group by some reaction.

[0015] (Formula (11))

Chemical formula

[0016] a is an integer of 0 or more, preferably an integer of 0 to 1,000, more preferably an integer of 10 to 300, still more preferably an integer of 10 to 150, for example, an integer of 15 to 70.

[0017] In one aspect, a is an integer of 10 to 1,000.

[0018] b is an integer of 0 or more, preferably an integer of 0 to 1,000, more preferably an integer of 10 to 300, still more preferably an integer of 10 to 150, for example, an integer of 15 to 70.

[0019] c is an integer of 0 or more, preferably an integer from 0 to 1,000, more preferably an integer from 10 to 300, still more preferably an integer from 10 to 150, and for example, an integer from 15 to 70.

[0020] The sum of a, b, and c is an integer of 2 or more, preferably an integer of 10 or more, more preferably an integer of 15 or more. The sum of a, b, and c is, for example, an integer of 3,000 or less, specifically, an integer of 1,500 or less, more specifically an integer of 1,000 or less, and particularly specifically, an integer of 300 or less, and for example, an integer of 100 or less.

[0021] In one aspect, the sum of a, b, and c may be an integer from 2 to 3,000, may be an integer from 2 to 1,500, or may be an integer from 10 to 1,000.

[0022] In one aspect, the sum of a, b, and c may be an integer from 2 to 1,000, may be an integer from 10 to 300, or may be an integer from 15 to 100.

[0023] The order of existence of the repeating units enclosed in parentheses with a, b, and c is arbitrary in formula (11).

[0024] In one aspect, a is an integer from 1 to 1,000, and b and c are 0.

[0025] In one aspect, b is an integer from 1 to 1,000, and a and c are 0.

[0026] In one aspect, c is an integer from 1 to 1,000, and a and b are 0.

[0027] R 1 is each independently a hydrogen atom or a monovalent organic group. R 1 is, in one aspect, a hydrogen atom. R 1 is, in one aspect, a monovalent organic group.

[0028] The above "monovalent organic group" is preferably C 1-20 Alkyl groups, groups having aryl groups, carbon-carbon double bonds, groups having phenyl groups, SiR 11 3-C 1-20 Alkylene group-, or Rf-ZC 1-20 It is an alkylene group, for example, C 1-20 It is an alkyl group.

[0029] C above 1-20 The alkyl group is preferably C 1-10 It is an alkyl group, more preferably C 1-6 These are alkyl groups, such as methyl, ethyl, propyl, and butyl groups.

[0030] The group having the aryl group is preferably C 6-10 C containing an aryl group 1-16 It is a monovalent hydrocarbon group. For example, an aryl group is a phenyl group, and a group having an aryl group is -(CH2) n2 It is represented as -Ph, where Ph represents a phenyl group. n2 is an integer from 0 to 20, for example, an integer from 1 to 10.

[0031] The above-mentioned groups having a carbon-carbon double bond are preferably vinyl groups, allyl groups, butenyl groups, pentenyl groups, and hexenyl groups. For example, the carbon-carbon double bond is located at the terminal portion, in other words, at the portion furthest from the Si atom to which the group having the carbon-carbon double bond is attached.

[0032] The group having the phenyl group is preferably a phenyl group or a benzyl group.

[0033] The above SiR 11 3-C 1-20 The alkylene group is preferably SiR 11 3-C 1-10 Alkylene group -, more preferably SiR 11 3-C 1-5 It is an alkylene group, for example, a (SiCH3)3-CH2CH2- group.

[0034] R 11 Each of them is independent of C 1-20 It is an alkyl group, preferably C 1-6 It is an alkyl group, and more preferably a methyl group.

[0035] The above Rf-ZC 1-20 Rf in the alkylene group is a C having at least one fluorine atom. 1-16 It is an alkyl group. 1-16 The alkyl group may be linear or branched, preferably linear or branched C 1-6 Alkyl groups, especially C 1-3 It is an alkyl group, more preferably a linear C 1-6 Alkyl groups, especially C 1-3 It is an alkyl group.

[0036] The above Rf is CF2H-C 1-15 It may also be a perfluoroalkylene group, C 1-16 A perfluoroalkyl group may also be used.

[0037] C above 1-16 The perfluoroalkyl group may be linear or branched, preferably linear or branched C 1-6 Perfluoroalkyl groups, especially C 1-3 A perfluoroalkyl group, more preferably a linear C 1-6 Perfluoroalkyl groups, especially C 1-3 Perfluoroalkyl groups, specifically -CF3, -CF2CF3, or -CF2CF2CF3.

[0038] The above Rf-ZC 1-20 C at alkylene group 1-20 The alkylene group is preferably C 1-10 It is an alkylene group, and more C 1-6 It is an alkylene group.

[0039] Z is O, C(=O)NR 9 , NR9 C(=O), C(=O)O, OC(=O), NR 9 C(=O)O, OC(=O)NR 9 、or NR 9 C(=O)NR 9 is. Note that the left side of Z is the Rf group and the right side is C 1-20 is bonded to the alkylene group, respectively. R 9 is each independently a hydrogen atom, a phenyl group or a C 1-6 alkyl group, preferably a hydrogen atom.

[0040] R 2 is each independently a hydrogen atom or a monovalent organic group. R 2 is, in one embodiment, a hydrogen atom. R 2 is, in one embodiment, a monovalent organic group. The monovalent organic group is R 1 has the same meaning as.

[0041] R 4 is each independently a hydrogen atom or a monovalent organic group. R 4 is, in one embodiment, a hydrogen atom. R 4 is, in one embodiment, a monovalent organic group. The monovalent organic group is R 1 has the same meaning as.

[0042] R 5 is each independently a hydrogen atom or a monovalent organic group. R 5 is, in one embodiment, a hydrogen atom. R 5 is, in one embodiment, a monovalent organic group. The monovalent organic group is R 1 has the same meaning as.

[0043] R 6 is each independently a hydrogen atom or a monovalent organic group. R 6 is, in one embodiment, a hydrogen atom. R 6 is, in one embodiment, a monovalent organic group. The monovalent organic group is R 1 has the same meaning as.

[0044] R Si These are, independently, -(O-SiR 7 2) m -OSiR 1 2R 2 That is. R 1 and R 2 These terms are equivalent to the above.

[0045] R 7 In one embodiment, it is a monovalent organic group. 7 In one direct route, R Si’ Therefore, a monovalent organic group is R 1 It is synonymous with [the above].

[0046] R Si’ R Si It is synonymous with [the above].

[0047] R as described in equation (11) Si Medium, -OSiR 1 2R 2 This can be up to 300, and preferably 1 to 100.

[0048] m is an integer greater than or equal to 0, preferably an integer between 0 and 1,000, and more preferably an integer between 0 and 100.

[0049] R 1 , R 2 , R 4 , R 5 , R 6 and R 7 At least one of them is equation (2): [ka] It is a base represented by .

[0050] Preferably, R 1 , R 2 , R 4 , R 5 , R 6 and R 7 In this, at least one is a base represented by formula (2), Of the other groups (i.e., groups other than those represented by formula (2)), R 1 , R 2 , R 4 , R 5 and R 6 Each of these is independently a monovalent organic group that does not contain a hydrogen atom or a group represented by formula (2), R 7 Each of them is independent of R Si’ Alternatively, a monovalent organic group that does not contain the group represented by formula (2), A monovalent organic group that does not contain the group represented by formula (2) above is C 1-20 Alkyl groups, groups having aryl groups, carbon-carbon double bonds, groups having phenyl groups, SiR 11 3-C 1-20 Alkylene group-, or Rf-ZC 1-20 It is an alkylene group, R Si’ R Si It is synonymous with [the above].

[0051] In one embodiment, R 1 and R 2 At least one of these is a base represented by formula (2).

[0052] In one embodiment, polyorganosiloxanes are represented by formula (13). [ka]

[0053] In equation (13), the sum of a1, a2, and a3 is a. The sum of a1, a2, and a3 is an integer greater than or equal to 10, and the order of existence of the repeating units a1, a2, a3, b, and c, enclosed in parentheses, is arbitrary within the equation.

[0054] a1 is a non-negative integer, for example, an integer between 0 and 100.

[0055] a2 is a non-negative integer, for example, an integer between 0 and 100.

[0056] a3 is an integer greater than or equal to 0, preferably an integer greater than or equal to 1. For example, a3 is an integer between 0 and 100, specifically an integer between 1 and 100.

[0057] In one embodiment, a1 is an integer between 10 and 150, and a2 and a3 are 0.

[0058] In one embodiment, a1 is an integer between 10 and 150, a2 is 0, and a3 is 1.

[0059] In one embodiment, a1 is an integer between 0 and 300, a2 is an integer between 0 and 300, and a3 is an integer between 1 and 300, preferably a1 is an integer between 0 and 100, a2 is an integer between 0 and 100, and a3 is an integer between 1 and 100.

[0060] In equation (13), b, c, R 1 , R 2 , R 6 and R Si These terms are equivalent to the above.

[0061] R 41 , R 42 and R 43 is R 4 This is an example. 51 , R 52 and R 53 is R 5 This is one example.

[0062] R 41 Each of these is independently a hydrogen atom or C 1-20 It is an alkyl group, preferably C 1-10 It is an alkyl group, and more preferably C 1-6 It is an alkyl group, such as a methyl group, ethyl group, propyl group, or butyl group, and specifically a methyl group.

[0063] R 51 Each of these is independently a hydrogen atom or C 1-20 It is an alkyl group, preferably C 1-10It is an alkyl group, more preferably C 1-6 It is an alkyl group, such as a methyl group, ethyl group, propyl group, or butyl group, and specifically a methyl group.

[0064] R 42 These are, independently, a group having an aryl group, a group having a carbon-carbon double bond, and SiR 11 3-C 1-20 Alkylene group-, or Rf-ZC 1-20 It is an alkylene group. 11 Rf and Z have the same meaning as described above.

[0065] R 52 These are, independently, hydrogen atoms and C 1-20 Alkyl groups, groups having aryl groups, carbon-carbon double bonds, groups having phenyl groups, SiR 11 3-C 1-20 Alkylene group-, or Rf-ZC 1-20 It is an alkylene group. 11 Rf and Z have the same meaning as described above.

[0066] In one embodiment, R 42 These are, independently, a group having an aryl group, a group having a carbon-carbon double bond, and SiR 11 3-C 1-20 Alkylene group-, or Rf-ZC 1-20 It is an alkylene group, R 52 C 1-20 It is an alkyl group.

[0067] In one embodiment, R 42 and R 52 These are, independently, a group having an aryl group, a group having a carbon-carbon double bond, and SiR 11 3-C 1-20 Alkylene group-, or Rf-ZC 1-20 It is an alkylene group.

[0068] R 43 This is the base represented by equation (2).

[0069] R 53 These are, independently, hydrogen atoms and C 1-20 It is an alkyl group or a group represented by formula (2).

[0070] In one embodiment, R 43 is a group represented by formula (2), and R 53 Each of these is independently a hydrogen atom or C 1-20 It is an alkyl group.

[0071] In one embodiment, R 43 and R 53 These are each independent bases represented by equation (2).

[0072] In a preferred embodiment, in formula (11), R 1 Each of these is independently a hydrogen atom or a monovalent organic group; R 2 Each of these is independently a hydrogen atom or a monovalent organic group; However, R 1 and R 2 At least one of them is a base represented by formula (2), R 4 Each of these is independently a hydrogen atom or a monovalent organic group; R 5 Each of these is independently a hydrogen atom or a monovalent organic group; R 6 Each of these is independently a hydrogen atom or a monovalent organic group; R Si These are, independently, -(O-SiR 7 2) m -OSiR 1 2R 2 and; R 7 Each of these is independently a monovalent organic group or R Si’ and; R Si’ R Si It is synonymous with; m is a non-negative integer; a is a non-negative integer; b is a non-negative integer; c is a non-negative integer; The sum of a, b, and c is an integer greater than or equal to 10; The order in which the repeating units labeled a, b, and c are enclosed in parentheses is arbitrary within the expression.

[0073] In another preferred embodiment, the polyorganosiloxane of formula (11) is represented by formula (13), In formula (13): R 1 Each of these is independently a hydrogen atom or a monovalent organic group; R 2 Each of these is independently a hydrogen atom or a monovalent organic group; R 6 Each of these is independently a hydrogen atom or a monovalent organic group; R Si These are, independently, -(O-SiR 7 2) m -OSiR 1 2R 2 and; R 7 Each of these is independently a monovalent organic group or R Si’ and; R Si’ R Si It is synonymous with; m is a non-negative integer; R 41 Each of these is independently a hydrogen atom, or C 1-20 It is an alkyl group; R 51 Each of these is independently a hydrogen atom, or C 1-20 It is an alkyl group; R 42 These are, independently, a group having an aryl group, a group having a carbon-carbon double bond, and SiR 11 3-C 1-20 Alkylene group-, or Rf-ZC 1-20 It is an alkylene group; R 11 Each of them is independent of C 1-20 It is an alkyl group; Rf is a C having at least one fluorine atom. 1-16 It is an alkyl group; Z is O, C(=O)NR 9 , NR 9 C(=O), C(=O)O, OC(=O), NR 9 C(=O)O, OC(=O)NR 9 , or NR 9 C(=O)NR 9 and; R 9 Each of these is independently a hydrogen atom, a phenyl group, or C 1-6 It is an alkyl group; R 52 These are, independently, hydrogen atoms and C 1-20 Alkyl groups, groups having aryl groups, carbon-carbon double bonds, groups having phenyl groups, SiR 11 3-C 1-20 Alkylene group-, or Rf-ZC 1-20 It is an alkylene group; R 43 These are, independently, bases represented by equation (2); R 53 These are, independently, hydrogen atoms and C 1-20 It is an alkyl group or a group represented by formula (2); a1 is a non-negative integer; a2 is a non-negative integer; a3 is an integer greater than or equal to 1; However, the sum of a1, a2, and a3 is a; a is 10 or greater; b and c are each non-negative integers; The order in which the repeating units, labeled a1, a2, a3, b, and c and enclosed in parentheses, exist within the expression is arbitrary.

[0074] Examples of polyorganosiloxanes of formula (11) include the following structures. [ka] n=34 [ka] n=34 [ka] x=27, y=2, z=1

[0075] (Formula (12)) Formula (12) represents the following cyclic siloxane compound. [ka]

[0076] d is an integer greater than or equal to 1, preferably an integer between 10 and 1,000, more preferably an integer between 10 and 300, and even more preferably an integer between 10 and 100.

[0077] In one embodiment, d is an integer between 10 and 1,000.

[0078] R in equation (12) 4 and R 5 These terms are equivalent to the above.

[0079] In equation (12), R 4 and R 5 Preferably, at least one of the groups is represented by formula (2), and the other groups are, independently, a hydrogen atom, C 1-20 Alkyl groups, groups having aryl groups, carbon-carbon double bonds, groups having phenyl groups, SiR 11 3-C 1-20 Alkylene group-, or Rf-ZC 1-20 It is an alkylene group. 11 Rf and Z have the same meaning as described above.

[0080] C above 1-20 The alkyl group is preferably C 1-10 It is an alkyl group, more preferably C 1-6 These are alkyl groups, such as methyl, ethyl, propyl, and butyl groups.

[0081] The group having the aryl group is preferably C 6-10 C containing an aryl group 1-16 It is a monovalent hydrocarbon group. For example, an aryl group is a phenyl group, and a group having an aryl group is -(CH2) n2 It is represented as -Ph, where Ph represents a phenyl group. n2 is an integer from 0 to 20, for example, an integer from 1 to 10.

[0082] The above-mentioned groups having a carbon-carbon double bond are preferably vinyl groups, allyl groups, butenyl groups, pentenyl groups, and hexenyl groups. For example, the carbon-carbon double bond is located at the terminal portion, in other words, at the portion furthest from the Si atom to which the group having the carbon-carbon double bond is attached.

[0083] The group having the phenyl group is preferably a phenyl group or a benzyl group.

[0084] The above SiR 11 3-C 1-20 The alkylene group is preferably SiR 11 3-C 1-10 Alkylene group -, more preferably SiR 11 3-C 1-5 It is an alkylene group, for example, a (SiCH3)3-CH2CH2- group. R 11 Each of them is independent of C 1-20 It is an alkyl group, preferably C 1-6 It is an alkyl group, and more preferably a methyl group.

[0085] The above Rf-ZC 1-20 Rf in the alkylene group is a C having at least one fluorine atom. 1-16 It is an alkyl group. 1-16 The alkyl group may be linear or branched, preferably linear or branched C 1-6 Alkyl groups, especially C 1-3 It is an alkyl group, more preferably a linear C1-6 Alkyl groups, especially C 1-3 It is an alkyl group.

[0086] The above Rf is CF2H-C 1-15 It may also be a perfluoroalkylene group, C 1-16 A perfluoroalkyl group may also be used.

[0087] C above 1-16 The perfluoroalkyl group may be linear or branched, preferably linear or branched C 1-6 Perfluoroalkyl groups, especially C 1-3 A perfluoroalkyl group, more preferably a linear C 1-6 Perfluoroalkyl groups, especially C 1-3 Perfluoroalkyl groups, specifically -CF3, -CF2CF3, or -CF2CF2CF3.

[0088] The above Rf-ZC 1-20 C at alkylene group 1-20 The alkylene group is preferably C 1-10 It is an alkylene group, and more C 1-6 It is an alkylene group.

[0089] Z is O, C(=O)NR 9 , NR 9 C(=O), C(=O)O, OC(=O), NR 9 C(=O)O, OC(=O)NR 9 , or NR 9 C(=O)NR 9 That is the case. Note that the left side of Z is an Rf group, and the right side is C. 1-20 They bond to the alkylene group, respectively. R 9 Each of these is independently a hydrogen atom, a phenyl group, or C 1-6 It is an alkyl group, preferably a hydrogen atom.

[0090] Examples of polyorganosiloxanes of formula (12) include the following structures. [ka] R 4 and R 5 R 44 It is represented as R 44 Each of the groups consists of at least one group represented by formula (2), and the other groups are, independently of each other, a hydrogen atom, C 1-20 Alkyl groups, groups having aryl groups, carbon-carbon double bonds, groups having phenyl groups, SiR 11 3-C 1-20 Alkylene group-, or Rf-ZC 1-20 It is an alkylene group.

[0091] R 44 Preferably, one of the groups is represented by formula (2), and the other groups are each independently a hydrogen atom, C 1-20 Alkyl groups, groups having aryl groups, carbon-carbon double bonds, groups having phenyl groups, SiR 11 3-C 1-20 Alkylene group-, or Rf-ZC 1-20 It is an alkylene group.

[0092] (Formula (2)) [ka]

[0093] X 1 is a hydrogen atom or a protecting group. In one embodiment, X 1 is a hydrogen atom. In one embodiment, X 1 This is a protecting group.

[0094] Protecting groups are groups that protect hydroxyl groups. Examples of protecting groups include ether-based protecting groups (e.g., benzyl group, allyl group, methyl group, p-methoxybenzyl group, triphenylmethyl group, etc.), silyl-based protecting groups (e.g., trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, triisopropylsilyl group, tert-butyldiphenylsilyl group, etc.), acetal-based protecting groups (e.g., 2-tetrahydropyranyl group, methoxymethyl group, methoxyethoxymethyl group, benzylidene acetal group, etc.), acyl-based protecting groups (e.g., benzoyl group, acetyl group, pivaloyl group, etc.), and cyclic carbonate groups.

[0095] The above protecting group can be removed, for example, by a reaction using an acid. Examples of acids include hydrochloric acid, sulfuric acid, and trifluoroacetic acid.

[0096] n1 is an integer greater than or equal to 2, and there is no particular upper limit, but for example, it is 5.

[0097] If n1 is 2, then -OX 1 It is located at the 2,3, 2,4, 2,5, 2,6, 3,4, or 3,5 positions of the phenyl group. Specifically, the group represented by formula (2) is one of the following structures. [ka]

[0098] If n1 is 3, then -OX 1 It can be present at the 2,3,4, 2,3,5, 2,3,6, 3,4,5, or 3,4,6 positions of the phenyl group. Specifically, formula (2) is one of the following structures. [ka]

[0099] If n1 is 4, then -OX 1It can be located at the 2,3,4,5, 2,3,4,6, or 2,3,5,6 positions of the phenyl group. Specifically, formula (2) is one of the following structures. [ka]

[0100] If n1 is 5, then -OX 1 It can be located at the 2, 3, 4, 5, and 6 positions of the phenyl group. [ka]

[0101] Preferably, n1 is 3 or greater, and more preferably 3.

[0102] Preferably, n1 is 3, -OX 1 They are located in 3rd, 4th, and 5th place.

[0103] Y 1 It is a linker that bonds a Si atom to a benzene ring, and is a single bond or a 2-10 valent organic group. 1 The left side is bonded to a Si atom, and the right side is bonded to a benzene ring.

[0104] Y 1 Preferably, it is a 2- to 10-valent organic group.

[0105] In one embodiment, Y 1 These are thioethers (-S-) and amides (-C(=O)NR 94 - is R 94 Each of these is independently a hydrogen atom, a phenyl group, or C 1-6 Represents an alkyl group (preferably a methyl group).

[0106] Y 1 Preferably, each is independent of the others. -(R 91 ) p1 -(X a ) q1 -R 92 - It is represented as follows: 1 The left side is bonded to a Si atom, and the right side is bonded to a phenyl group. R 91 This is a single bond, -(CH2) p2 - or o-, m- or p-phenylene group, preferably -(CH2) p2 - is p2 is an integer from 1 to 20, preferably an integer from 1 to 6, more preferably an integer from 1 to 3, and even more preferably 1 or 2. X a is, -(X b ) q2 - represents, X b These are, independently, -O-, -S-, o-, m- or p-phenylene groups, -(OR 95 ) p4 -, -C(O)O-, -Si(R 93 )2-,-(Si(R 93 )2O) p5 -Si(R 93 )2-, -CONR 94 -, -O-CONR 94 -, -NR 94 -and-(CH2) p6 - Represents a base selected from a group consisting of -. R 93 These are, independently, a phenyl group and a C 1-6 Alkyl alkyl group or C 1-6 Represents an alkoxy group, preferably a phenyl group or C 1-6 It is an alkyl group, and more preferably a methyl group. R 94 Each of these is independently a hydrogen atom, a phenyl group, or C 1-6 Represents an alkyl group (preferably a methyl group). R 95 Each of them is independent of C 1-6 It is an alkylene group. Each of the p4 values ​​is an independent integer between 1 and 5. Each of the p5s is an integer between 1 and 100, preferably between 1 and 20, independently. Each of the p6s is an integer between 1 and 20, preferably between 1 and 6, and more preferably between 1 and 3. q2 is an integer between 1 and 10, preferably between 1 and 5, and more preferably between 1 and 3. p1 is either 0 or 1. q1 is either 0 or 1. The order in which each repeating unit, denoted as p1 or q1 and enclosed in parentheses, exists is arbitrary. Here, at least one of p1 and q1 is 1. R 92 This is a single bond, -(CH2) p3 - or o-, m- or p-phenylene group, preferably -(CH2) p3 - is p3 is an integer between 1 and 20, preferably between 2 and 6, and more preferably between 2 and 3. Here, Y 1 (typically Y 1 The hydrogen atom of the fluorine atom, C 1-3 Alkyl and C 1-3 It may be substituted with one or more substituents selected from fluoroalkyl groups. In a preferred embodiment, Y 1 These groups are not substituted by these groups.

[0107] In one embodiment, Y 1 Each of them operates independently. -(R 91 ) p1 -(X a ) q1 - It is represented as follows. R 91 , X a p1 and q1 have the same meaning as described above.

[0108] In one embodiment, Y 1 It does not contain the group represented by -NHC(=O)-.

[0109] In one embodiment, Y 1It does not contain esters, secondary amines, amides, ethers, thioethers, or thioesters. An example of an ester is -CO-O-. An example of a secondary amine is -NHCH3. Examples of amides include -CO-NH-. Examples of ethers include -O-CH3. An example of a thioether is -CH2-SCH3. Examples of thioesters include -CH2-CO-SCH3.

[0110] In one embodiment, Y 1 It does not contain the group represented by -CH2-NH-.

[0111] In one embodiment, Y 1 It does not contain the group represented by -CH2-N=CH-.

[0112] Y 1 is more C 1-20 It is an alkylene group, and more preferably C 1-10 It is an alkylene group, and particularly preferably C 1-5 It is an alkylene group, for example, a C3 alkylene group.

[0113] In one embodiment, organosiloxane is represented by formula (13), One R 2 is a base represented by equation (2); Other R 1 , R 2 , R 41 and R 51 Each of these is independently a hydrogen atom or C 1-20 It is an alkyl group; R 41 and R 51 Each of these is independently a hydrogen atom or C 1-20 It is an alkyl group; a1 is an integer between 1 and 300, and a2, a3, b, and c are 0.

[0114] In the above embodiment, for example, One R 2 is a base represented by equation (2); Other R 1 , R 2 R 41 and R 51 It is a methyl group; a1 is an integer between 1 and 300, and a2, a3, b, and c are 0.

[0115] In the above embodiment, as another example, One R 2 is a base represented by equation (2); Another one R 2 It is a C4 alkyl group; R 1 , R 41 and R 51 It is a methyl group; a1 is an integer between 1 and 300, and a2, a3, b, and c are 0. For example, equation (13) can be expressed as equation (14), and R 1a is a group represented by formula (2), and R 1b It is a C4 alkyl group. [ka]

[0116] In one embodiment, R 2 These are, independently, bases represented by equation (2); R 1 , R 41 and R 51 Each of these is independently a hydrogen atom or C 1-20 It is an alkyl group; a1 is an integer between 1 and 300, and a2, a3, b, and c are 0. For example, R 2a and R 2b These are each independent bases represented by equation (2). [ka]

[0117] In the above embodiment, for example, R 2a and R 2b These are, independently, bases represented by equation (2); R 1 , R 41 and R 51 It is a methyl group; a1 is an integer between 1 and 300, and a2, a3, b, and c are 0.

[0118] In one embodiment, organosiloxanes are represented by formula (13). R 1 , R 2 , R 41 , R 51 , R 52 and R 53 is a methyl group; R 42 is SiR 11 3-C 1-20 It is an alkylene group; R 11 It is a methyl group; R 43 is a base represented by equation (2); a1 is an integer between 0 and 300; a2 is an integer between 0 and 300; a3 is 1; The sum of a1, a2, and a3 is an integer greater than or equal to 10; b and c are 0; The order in which the repeating units, labeled a1, a2, a3, b, and c and enclosed in parentheses, exist within the expression is arbitrary.

[0119] In one embodiment, the polyorganosiloxane of formula (1) does not contain a fluorine atom.

[0120] In one embodiment, the polyorganosiloxane of formula (1) contains a fluorine atom.

[0121] [Composition] This section describes compositions (release agents) containing polyorganosiloxanes.

[0122] (solvent) The above composition preferably contains a solvent.

[0123] In one embodiment, the solvent includes an organic solvent, for example, the solvent consists solely of an organic solvent.

[0124] Examples of organic 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 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 low boiling point (at most 150°C) silicone solvents such as hexamethyldisiloxane and heptamethyltrisiloxane.

[0125] In one embodiment, the solvent includes an aqueous medium, where the aqueous medium refers to water alone or a mixture of water and an organic solvent.

[0126] When the solvent is an aqueous medium, the organic solvent contained in the solvent may be a water-miscible organic solvent. The amount of water-miscible organic solvent may be 30 parts by mass or less, for example, 10 parts by mass or less (preferably 0.1 parts by mass or more), per 100 parts by mass of solvent. Examples of water-miscible organic solvents include alcohols such as ethanol, propyl alcohol, and isopropyl alcohol; and ethers.

[0127] In one aspect, the solvent is water.

[0128] The solvent may be present in 70 to 90 parts by mass, or 90 to 99 parts by mass, per 100 parts by mass of the composition.

[0129] (Other ingredients) The above composition may further contain other components. Examples of other components include emulsifiers, additives, and silicone compounds.

[0130] As an emulsifier, at least one selected from nonionic emulsifiers, cationic emulsifiers, anionic emulsifiers, and amphoteric emulsifiers may be used. As the emulsifier, compounds with structures other than those described as polyorganosiloxanes may be used. In particular, when the solvent is an aqueous medium, the polyorganosiloxane can be dissolved, dispersed, or suspended by adding an emulsifier.

[0131] Examples of the emulsifiers mentioned above include nonionic emulsifiers such as aliphatic alcohols, ethoxylated aliphatic alcohols, ethoxylated oxo alcohols and other alcohol ethers, aliphatic amines (e.g., dimethylalkylamines), fatty acid alkanolamides, glycerol esters or polyglycerol esters, or sorbitol esters, as well as alcohol-fatty acid esters; cationic surfactants such as quaternary ammonium salts and alkylamine salts; anionic emulsifiers such as alkyl ether carboxylates, alkyl sulfates, fatty alcohol ethoxylate ether sulfates, α-olefin sulfonates, alkyl phosphates, and alkyl sulfosuccinates; and amphoteric emulsifiers. These emulsifiers may be used individually or in combination. The emulsifier may be included in the composition in an amount of, for example, 0.5 to 20 parts by mass, specifically 1 to 10 parts by mass, per 100 parts by mass of the composition.

[0132] Examples of additives include catalysts, crosslinking agents, thickeners, pH adjusters, silicon-containing compounds, waxes, acrylic emulsions, fluorine-containing polymers, drying rate regulators, film-forming aids, compatibilizers, antifreeze agents, viscosity modifiers, UV absorbers, antioxidants, defoaming agents, texture modifiers, slipperiness modifiers, antistatic agents, hydrophilic agents, antibacterial agents, preservatives, insecticides, fragrances, flame retardants, and alcohols (e.g., 2-aminoethanol, methanol, etc.). Specifically, examples include catalysts, crosslinking agents, thickeners, or pH adjusters.

[0133] Examples of the catalysts mentioned above include organometallic salts (preferably having 1 to 30 carbon atoms), such as organotitanium compounds such as titanium ethyl acetate and titanium triethanolamine, dibutyltin dilaurate, dibutyltin diacetate, tetrabutyl titanate (butoxytitanium), tetraisopropyl titanate (isopropoxytitanium), bis-(acetylacetonyl)-diisopropyl titanate, bis(ethylacetoacetate)diisopropyl titanate {bis(ethylacetoacetate)diisopropoxytitanium}, other chelates of titanium and zirconium, acids (especially organic acids having 1 to 10 carbon atoms), such as acetic acid or propionic acid, and carboxylates.

[0134] Examples of the crosslinking agents mentioned above include silane coupling agents such as methyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, and 3-aminopropyltrimethoxysilane, as well as blocked isocyanates.

[0135] Examples of the thickening agents mentioned above include cellulose-based thickeners such as cellulose gum, methylcellulose, ethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, hydrophobized hydroxypropylmethylcellulose, sodium cellulose sulfate, and cellulose powder; highly polymerized polyethylene glycol; plant-based thickeners such as gum arabic, locust bean gum, tara gum, guar gum, glucomannan, xanthan gum, pectin, and agar; starches such as starch, carboxymethyl starch, and methylhydroxypropyl starch; alginic acid-based polymers such as sodium alginate and propylene glycol alginate; and polymers such as carboxyvinyl polymer, acrylic acid / alkyl methacrylate copolymer, acrylates / alkyl acrylate crosspolymer, sodium polyacrylate, and polyurethane.

[0136] The above pH adjusters include formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, palmitic acid, margaric acid, stearic acid, oleic acid, linoleic acid, linolenic acid, arachidonic acid, docosahexaenoic acid, eicosapentaenoic acid, lactic acid, malic acid, citric acid, benzoic acid, phthalic acid, isophthalic acid, terephthalic acid, salicylic acid, gallic acid, melitic acid, cinnamic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, fumaric acid, maleic acid, aconitic acid, amino acids, anthracite. Examples include carboxylic acids such as nilic acid, organic acids such as sulfonic acids and organic phosphonic acids; inorganic acids such as nitric acid, carbonic acid, hydrochloric acid, phosphoric acid, hypophosphorous acid, phosphorous acid, phosphonic acid, boric acid, hydrofluoric acid, orthophosphoric acid, pyrophosphoric acid, polyphosphoric acid, metaphosphoric acid, and hexametaphosphoric acid; alkali metal hydroxides such as potassium hydroxide (KOH) and sodium hydroxide (NaOH); alkali metal carbonates such as potassium carbonate (K2CO3) and sodium carbonate (Na2CO3); hydroxides of group 2 elements; ammonia (ammonium hydroxide); and organic bases such as quaternary ammonium hydroxide compounds.

[0137] In one embodiment, the composition comprises an emulsifier and an aqueous solvent.

[0138] In one embodiment, the composition comprises at least one of a catalyst, a crosslinking agent, a thickening agent, and a pH adjuster, and an organic solvent.

[0139] In one embodiment, the composition comprises at least one of a catalyst, a crosslinking agent, a thickening agent, and a pH adjuster, and an aqueous medium.

[0140] In one embodiment, the composition of the present disclosure comprises a linear or cyclic siloxane compound having a number average molecular weight of 1,000 or less (hereinafter sometimes referred to as "siloxane compound with a molecular weight of 1,000 or less"). The number average molecular weight can be determined, for example, by converting it to polystyrene in gel permeation chromatography (GPC) analysis using tetrahydrofuran or the like as the developing solvent. Note that the siloxane compound with a molecular weight of 1,000 or less is different from the polyorganosiloxane represented by formula (11) or formula (12).

[0141] The siloxane compounds with a molecular weight of 1,000 or less mentioned above include the following siloxane compounds (B1) to (B3): Octamethylcyclotetrasiloxane (B1); Decamethylcyclopentasiloxane (B2); Dodecamethylcyclohexasiloxane (B3); At least one of these can be listed.

[0142] The above siloxane compound (B1) is octamethylcyclotetrasiloxane, represented by the following formula. TIFF2026083361000030.tif4342

[0143] The above siloxane compound (B2) is decamethylcyclopentasiloxane, represented by the following formula. TIFF2026083361000031.tif4654

[0144] The above siloxane compound (B3) is dodecamethylcyclohexasiloxane, represented by the following formula. TIFF2026083361000032.tif4247

[0145] The above siloxane compounds (B1) to (B3) may be present in an amount of 0 to 10,000 ppm by mass relative to the polyorganosiloxane.

[0146] In one embodiment, the composition of the present disclosure is substantially free of the siloxane compounds (B1) to (B3). In this disclosure, "substantially free of siloxane compounds (B1) to (B3)" means that the content of siloxane compounds (B1) to (B3) in the composition is below the detection limit by gas chromatography or gas chromatography-mass spectrometry, relative to the content of polyorganosiloxane. For example, the content of siloxane compounds (B1) to (B3) is 3 ppm by mass or less, 2 ppm by mass or less, or 1 ppm by mass or less, respectively, relative to the content of polyorganosiloxane in the composition.

[0147] The content of siloxane compounds (B1) to (B3) relative to the polyorganosiloxane content in the composition of this disclosure can be measured by gas chromatography or gas chromatography-mass spectrometry. Specifically, 0.1 g of the sample to be measured is added to 10 mL of acetone and shaken for about 2 hours. The resulting solution is measured by gas chromatography or gas chromatography-mass spectrometry.

[0148] The compositions of this disclosure may contain a polyorganosiloxane, and the content of at least one of the siloxane compounds (B1) to (B3) may be 10,000 ppm by mass or less. The polyorganosiloxane and the siloxane compounds (B1) to (B3) may be intentionally mixed. The raw materials for the polyorganosiloxane or compounds derived from said raw materials that correspond to the siloxane compounds (B1) to (B3) may remain and coexist with the polyorganosiloxane.

[0149] Siloxane compounds (B1) to (B3) in the raw materials for polyorganosiloxane or compounds derived from said raw materials can be removed by known methods such as distillation, vacuum distillation, and thin-film distillation. For example, by bubbling nitrogen gas through the raw materials for polyorganosiloxane or compounds derived from said raw materials and distilling them off under reduced pressure at 80 to 150°C for 5 to 40 hours at a pressure of 100 mmHg or less, the amount of siloxane compounds (B1) to (B3) in the raw materials for polyorganosiloxane or compounds derived from said raw materials can be reduced to 10,000 ppm by mass or less.

[0150] The siloxane compound with a molecular weight of 1,000 or less may include at least one of the compounds (C1) to (C3) shown below.

[0151] The above compound (C1) is octamethyltrisiloxane, represented by the following formula. TIFF2026083361000033.tif2378

[0152] The above compound (C2) is a decamethyltetrasiloxane represented by the following formula. TIFF2026083361000034.tif2683

[0153] The above compound (C3) is 1,1,1,3,5,5,5-heptamethyl-3-[(trimethylsilyl)oxy]trisiloxane, represented by the following formula. TIFF2026083361000035.tif2560

[0154] The total content of compounds (C1) to (C3) may be 0 to 1,000 ppm by mass relative to the content of the polyorganosiloxane.

[0155] In one embodiment, the composition of the present disclosure is substantially free of the compounds (C1) to (C3). In this disclosure, "substantially free of compounds (C1) to (C3)" means that the content of compounds (C1) to (C3) in the composition is below the detection limit by gas chromatography or gas chromatography-mass spectrometry, relative to the content of polyorganosiloxane. For example, the content of compounds (C1) to (C3) is 3 ppm by mass or less, 2 ppm by mass or less, or 1 ppm by mass or less, respectively, relative to the content of polyorganosiloxane in the composition.

[0156] The content of compounds (C1) to (C3) in the composition of this disclosure relative to the content of polyorganosiloxane can be measured by gas chromatography or gas chromatography-mass spectrometry, similar to the content of siloxane compounds (B1) to (B3).

[0157] The above-mentioned other components may be included in amounts of, for example, 0.1 to 20 parts by mass, specifically 0.5 to 10 parts by mass, per 100 parts by mass of the above composition.

[0158] The above compositions may further include phosphoric acid or salts derived therefrom. By including such phosphoric acid or a salt thereof, the compositions of this disclosure can exhibit good mold release properties.

[0159] The concentration of the phosphoric acid or its salt is preferably 10 ppm by mass or less, more preferably 1 ppm by mass or less, more preferably 0.5 ppm by mass or less, and even more preferably 0.1 ppm by mass or less, per 100 parts by mass of the composition. The concentration of the phosphoric acid or its salt may be, for example, 0 to 1 ppm by mass, more specifically 0 to 0.5 ppm by mass, and more specifically 0 to 0.1 ppm by mass.

[0160] The above composition may be in the form of a solution, emulsion, suspension, aerosol, or the like.

[0161] In one embodiment, the composition is in solution form. In this embodiment, the composition is dissolved in a solution. This embodiment is preferred because it is easily volatile and allows for good work efficiency. However, a portion of the composition may not be dissolved in the solution.

[0162] In one embodiment, the composition is in emulsion form. This embodiment is preferred in terms of being environmentally friendly and safe for humans, from the viewpoint of volatility organic compound (VOC) regulations. In this case, the composition preferably contains an emulsifier as one of the other components.

[0163] In one embodiment, the composition is in aerosol form. In this case, it can be filled into an aerosol can using a propellant. Examples of propellants include LPG, dimethyl ether, and carbon dioxide. The amount of propellant is usually 10 to 95% by weight, preferably 20 to 90% by weight, and more preferably 30 to 90% by weight, relative to the total amount of release agent and propellant. If the amount of propellant is 10% by weight or more, better spraying is possible and a more uniform layer of release agent tends to be obtained. Also, if the amount of propellant is 95% by weight or less, the thickness of the layer formed from the composition tends not to become too thin, and the release properties do not tend to decrease too much.

[0164] The specific gravity of the above composition may be in the range of 0.8 to 1.2 or in the range of 0.9 to 1.1 at 25°C. The specific gravity can be measured using a float-type hydrometer.

[0165] The above composition preferably has a pH in the range of 8.0 to 12.0, and more preferably in the range of 9.0 to 11.0.

[0166] The above composition can be used as a mold release agent or a water-repellent and oil-repellent agent.

[0167] The above compositions can be prepared using methods known in the art.

[0168] The above composition can be used as an internal or external release agent. It is preferable that the above composition be used as an external release agent.

[0169] When the above composition is used as an external release agent, it can usually be used as follows: The composition (release agent) is applied to the inner surface of the mold, and if it contains a solvent, the solvent, etc., is dried and removed, after which a layer formed from the release agent is provided on the mold. The molding composition is filled into the mold to form the molding material, and the molding material is removed from the mold.

[0170] The above composition is surface-treated on the surface of a base material such as a metal mold made of aluminum, stainless steel, or iron, an epoxy resin mold or a wooden mold, or a nickel electroformed or chrome-plated mold, and a mold is provided.

[0171] [Molding method] An example of a molding method using the above composition is shown. Note that the following description is merely an example, and other methods may be used.

[0172] First, the substrate to be included in the mold is prepared. This substrate is surface-treated using the above composition to form a surface treatment layer (release layer). Heating may be performed as needed, for example, at 100 to 300°C. The heating time is not particularly limited, but for example, it is performed for 0 to 30 minutes. This forms the mold.

[0173] The molded material is processed using the obtained mold. At this time, a surface treatment layer formed from the above composition is bonded to the molded material.

[0174] Examples of molding materials include rubbers such as urethane rubber, H-NBR (hydrogenated nitrile rubber), NBR (nitrile rubber), silicone rubber, EPDM (ethylene-propylene-diene rubber), CR (chloroprene rubber), NR (natural rubber), fluororubber, SBR (styrene-butadiene rubber), BR (butadiene rubber), IIR (isobutylene-isoprene rubber), and IR (isoprene rubber); thermosetting resins such as urethane foam, epoxy resin, phenolic resin, and FRP (fiber-reinforced plastic; for example, CFRP (carbon fiber reinforced polymer) and GFRP (glass fiber reinforced plastic)); and thermoplastic resins such as ABS (acrylonitrile-butadiene-styrene copolymer synthetic resin), polycarbonate, and PBT (polybutylene terephthalate resin). Specifically, thermosetting resins such as urethane foam, epoxy resin, phenolic resin, and FRP include, for example, CFRP, which is epoxy resin with carbon fibers added as a reinforcing material.

[0175] The above molding can be performed using a molding machine. Examples of molding machines include autoclave molding, press molding, RTM (Resin Transfer Molding), filament winding molding, and injection molding, and specifically, press molding can be used. In press molding, a prepreg, which is a sheet that has been impregnated with resin in advance, is pressed with a press machine, which can shorten the molding cycle.

[0176] The above describes in detail the method for manufacturing a treated substrate having a surface treatment layer, and the substrate obtained by this method. However, the manufacturing method and substrate of this disclosure are not limited to those exemplified above. [Examples]

[0177] The present disclosure will be described below with reference to examples, but the present disclosure is not limited to the following examples.

[0178] In the following, Me represents a methyl group, and MOM represents a CH3OCH2- group.

[0179] (Synthesis Example 1: Synthesis of terminally gallol group-modified silicone) 5.00 g of organohydrogenpolysiloxane represented by formula (a), 0.50 g of vinylgallol MOM protected compound represented by formula (b), and 5.62 mL of anhydrous tetrahydrofuran were placed in a glass flask, and the flask was purged with nitrogen. 0.05 mL of xylene solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum concentration 2 wt%) was added to the flask, and the mixture was stirred at room temperature for 6 hours. 1 The disappearance of the hydrosilyl group peak in the starting material was confirmed by 1H-NMR, thus confirming the progress of the reaction. [ka] [ka]

[0180] Subsequently, 0.25 g of activated carbon was added to the flask and stirred for 16 hours, after which the activated carbon was removed by pressure filtration. Then, 3.00 mL of 6N hydrochloric acid aqueous solution and 8.00 mL of methanol were added to the flask and stirred at room temperature for 24 hours. 1 The reaction was confirmed by observing the disappearance of the MOM group peak using 1H-NMR. The hydrochloric acid was neutralized by adding aqueous sodium carbonate solution, and tetrahydrofuran and methanol were removed by vacuum distillation. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried, and the solvent was removed to obtain 4.12 g of the target product represented by formula (x1). In formula (x1), n ​​was 34. [ka]

[0181] (Synthesis Example 2: Synthesis of gallol group-modified silicone at both ends) 5.00 g of organohydrogenpolysiloxane represented by formula (c), 1.09 g of vinylgallol MOM protected compound represented by formula (b), and 5.62 mL of anhydrous tetrahydrofuran were placed in a glass flask, and the flask was purged with nitrogen. 0.05 mL of a xylene solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum concentration 2 wt%) was added to the flask, and the mixture was stirred at room temperature for 6 hours. 1 The disappearance of the hydrosilyl group peak in the starting material was confirmed by 1H-NMR, thus confirming the progress of the reaction. [ka]

[0182] Subsequently, 0.25 g of activated carbon was added to the flask and stirred for 16 hours, after which the activated carbon was removed by pressure filtration. Then, 6.00 mL of 6N hydrochloric acid aqueous solution and 10.00 mL of methanol were added to the flask and stirred at room temperature for 24 hours. At this point, the disappearance of the MOM group peak was confirmed by 1H-NMR, confirming the progress of the reaction. Hydrochloric acid was neutralized by adding sodium carbonate aqueous solution, and tetrahydrofuran and methanol were removed by vacuum distillation. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried, and the solvent was removed to obtain 4.68 g of the target product represented by formula (x2). In formula (x2), n was 34. [ka]

[0183] (Synthesis Example 3: Synthesis of Side-Chain Gallol Group Modified Silicone) 3.00 g of organohydrogenpolysiloxane represented by formula (d), 0.29 g of vinylgallol MOM protected compound represented by formula (b), and 3.37 mL of anhydrous tetrahydrofuran were placed in a glass flask, and the flask was purged with nitrogen. 0.03 mL of a xylene solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum concentration 2 wt%) was added to the flask, and the mixture was stirred at room temperature for 6 hours. 1The disappearance of the vinyl group peak in the starting material was confirmed by 1H-NMR, thus confirming the progress of the reaction. [ka]

[0184] Subsequently, 0.34 mL of vinyltrimethylsilyl was placed in the flask, and 0.03 mL of a xylene solution of gold-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum concentration 2 wt%) was added to the flask, and the mixture was stirred at room temperature for 6 hours. 1 The reaction was confirmed by observing the disappearance of the hydrosilyl group peak in the starting material via 1H-NMR. 0.30 g of activated carbon was added and stirred for 16 hours, after which the activated carbon was removed by pressure filtration. Then, 3.00 mL of 6N hydrochloric acid aqueous solution and 8.00 mL of methanol were added to the flask and stirred at room temperature for 24 hours. At this point, the reaction was confirmed by observing the disappearance of the MOM group peak via 1H-NMR. Hydrochloric acid was neutralized with sodium carbonate aqueous solution, and tetrahydrofuran and methanol were removed by vacuum distillation. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried, and the solvent was removed to obtain 2.48 g of the target product represented by formula (x3). In formula (x3), x=29, y=2, and z=1. [ka]

[0185] (Synthesis Example 4: Synthesis of Trimethoxysilane-Modified Silicone) 3.00 g of organohydrogenpolysiloxane represented by formula (a) and 0.16 mL of vinyltrimethoxysilane were placed in a glass flask, and the flask was purged with nitrogen. 0.03 mL of a xylene solution of gold-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum concentration 2 wt%) was added to the flask, and the mixture was stirred at room temperature for 6 hours. 1 The disappearance of the hydrosilyl group peak in the starting material was confirmed by 1H-NMR, thus confirming the progress of the reaction.

[0186] Subsequently, 0.13 g of activated carbon was added and stirred for 16 hours. After removing the activated carbon by pressure filtration, 2.64 g of the target substance represented by equation (x4) was obtained. In equation (x4), n was 34. [ka]

[0187] (Synthesis Example 5: Synthesis of Side-Chain Amino-Modified Silicones) In a glass flask, 3.00 g of hexamethylcyclotrisiloxane, 3.37 mL of anhydrous tetrahydrofuran, and 0.3 mL of triazabicyclo[4,4,0]deca-5-ene (0.4 g / mL aqueous solution) were charged and stirred at 40°C for 2 hours. Then, 0.09 mL of 3-(2-aminoethylamino)propyldimethoxysilane was added and stirred at 40°C for 2 hours, followed by the addition of 0.09 mL of hexamethyldisiloxane and stirring at 40°C for 2 hours. After that, tetrahydrofuran was removed by vacuum distillation to obtain 2.38 g of the target product represented by formula (x5). In formula (x5), x=29 and y=1.

[0188] Subsequently, tetrahydrofuran was removed by vacuum distillation to obtain 2.38 g of the target product represented by equation (x5). In equation (x5), x=29 and y=1. [ka]

[0189] (Synthesis Example 6: Synthesis of Side-Chain Epoxy Modified Silicone) 3.00 g of organohydrogenpolysiloxane represented by formula (d), 0.14 mL of 1,2-epoxy-5-hexene, and 3.47 mL of toluene were placed in a glass flask, and the flask was purged with nitrogen. 0.03 mL of a xylene solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum concentration 2 wt%) was added to the flask, and the mixture was stirred at 80°C for 24 hours. 1 The disappearance of the vinyl group peak in the starting material was confirmed by 1H-NMR, thus confirming the progress of the reaction.

[0190] Subsequently, 0.34 mL of vinyltrimethylsilyl was placed in the flask, and 0.03 mL of a xylene solution of gold-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum concentration 2 wt%) was added to the flask, and the mixture was stirred at room temperature for 6 hours. 1 The reaction was confirmed by observing the disappearance of the hydrosilyl group peak in the starting material via 1H-NMR. 0.30 g of activated carbon was added and the mixture was stirred for 16 hours, after which the activated carbon was removed by pressure filtration. Subsequently, toluene was removed by vacuum distillation to obtain 2.45 g of the target product represented by formula (x6). In formula (x6), x=29, y=2, and z=1. [ka]

[0191] (Synthesis Example 7: Synthesis of Side-Chain Trimethoxysilane-Modified Fluorosilicone) 5.00 g of organohydrogenpolysiloxane represented by formula (e) and 2.22 mL of vinyltrimethoxysilane were charged into a glass flask, and 5.62 mL of anhydrous tetrahydrofuran was added, and the flask was purged with nitrogen. 0.08 mL of a xylene solution of gold-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum concentration 2 wt%) was added to the flask and stirred at room temperature for 18 hours. 1 ¹H-NMR confirmed the disappearance of the hydrosilyl group peak, indicating that the entire amount of vinyltrimethoxysilane had reacted. [ka]

[0192] Subsequently, 4.56 mL of 5FP-AE represented by formula (f) was placed in the flask, and 0.10 mL of xylene solution of gold-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum concentration 2 wt%) was added to the flask, and the mixture was stirred at room temperature for 18 hours. 1The reaction was confirmed by observing the disappearance of the hydrosilyl group peak using 1H-NMR. Subsequently, 0.90 g of activated carbon was added and the mixture was stirred for 16 hours, after which the activated carbon was removed by pressure filtration. Tetrahydrofuran was then removed by vacuum distillation to obtain 10.64 g of the target product represented by equation (x7). In equation (x7), x=30, y=15, and z=30. [ka] [ka]

[0193] (Example 1) The solution was prepared by combining 0.5% by weight of a one-terminated gallol group-modified silicone represented by formula (x1) obtained in Synthesis Example 1 with 95.0% by weight of isohexane as a diluent.

[0194] (Example 2) The mixture was prepared to consist of 0.5% by weight of the terminally gallol group-modified silicone represented by formula (x2) obtained in Synthesis Example 2, and 95.0% by weight of the diluent isohexane.

[0195] (Example 3) The mixture was prepared to consist of 0.5% by weight of the side-chain gallol group-modified silicone represented by formula (x3) obtained in Synthesis Example 3, and 95.0% by weight of the diluent isohexane.

[0196] (Example 4) The procedure was the same as in Example 3, except that the solvent was changed to water.

[0197] (Comparative Example 1) The solution was prepared to consist of 0.5% by weight of a one-terminated trimethoxysilane-modified silicone represented by formula (x4) obtained in Synthesis Example 4, and 95.0% by weight of isohexane as a diluent.

[0198] (Comparative Example 2) The mixture was prepared to consist of 0.5% by weight of the side-chain amino-modified silicone represented by formula (x5) obtained in Synthesis Example 5, and 95.0% by weight of the diluent isohexane.

[0199] (Comparative Example 3) The mixture was prepared to consist of 0.5% by weight of the side-chain epoxy-modified silicone represented by formula (x6) obtained in Synthesis Example 6, and 95.0% by weight of the diluent isohexane.

[0200] (Comparative Example 4) The mixture was prepared to consist of 0.5% by weight of the side-chain trimethoxysilane-modified fluorosilicone represented by formula (x7) obtained in Synthesis Example 7, 49.75% by weight of the diluting solvent isohexane, and 49.75% by weight of isopropyl alcohol.

[0201] (Comparative Example 5) The procedure was the same as in Comparative Example 4, except that the solvent was changed to water.

[0202] [Method for evaluating mold release properties] A release agent was applied to an aluminum substrate and heated and cured at 150°C for 15 minutes to create a release agent coating. A CFRP prepreg was placed on a release agent coating, and a heat-resistant adhesive tape was applied on top of it. Then, an aluminum substrate was placed on the heat-resistant adhesive tape, sandwiching the release agent coating, prepreg, and heat-resistant adhesive tape between the aluminum substrates. The mixture was then heat-molded at 150°C using a heat press. Afterward, the molded heat-resistant adhesive tape was lifted using a push-bull gauge. This caused the release agent coating and prepreg to separate. The peak value at the time of separation was measured and defined as the initial release property (N).

[0203] The results are shown in the table below.

[0204] [Table 1]

[0205] As shown in Table 1, it was found that using gallol groups resulted in reduced initial peelability and lower adhesion to CFRP. In Comparative Examples 1-3, modified sites other than gallol groups were used, resulting in increased initial delamination. In other words, the bonding properties with CFRP improved, making delamination more difficult. In Comparative Example 4, fluorosilicone was used, resulting in improved adhesion with CFRP and reduced peeling. Both Example 4 and Comparative Example 5 were investigated using emulsion-type materials. It was found that Example 4 exhibited lower initial peelability and lower adhesion to CFRP. [Industrial applicability]

[0206] According to this disclosure, it is possible to provide a polyorganosiloxane contained in a mold release agent that exhibits better release properties from synthetic resins and the like after molding.

Claims

1. Formula (11) below: 【Chemistry 1】 [In the formula: R １ Each of these is independently a hydrogen atom or a monovalent organic group; R ２ Each of these is independently a hydrogen atom or a monovalent organic group; R ４ Each of these is independently a hydrogen atom or a monovalent organic group; R ５ Each of these is independently a hydrogen atom or a monovalent organic group; R ６ Each of these is independently a hydrogen atom or a monovalent organic group; R Ｓｉ is, independently of each other, -(O-SiR ７ ２ ), ｍ -OSiR １ ２ R ２ ; R ７ Each of these is independently a monovalent organic group or R Ｓｉ’ And; R Ｓｉ’ R Ｓｉ It is synonymous with; m is a non-negative integer; However, R １ , R ２ , R ４ , R ５ , R ６ and R ７ At least one of them is equation (2): 【Chemistry 2】 It is a base represented by; X １ is a hydrogen atom or a protecting group; Y １ These are single bonds or divalent to decavalent organic groups; n1 is an integer greater than or equal to 2; a is a non-negative integer; b is a non-negative integer; c is a non-negative integer; The sum of a, b, and c is an integer greater than or equal to 2; The order in which the repeating units labeled a, b, and c are enclosed in parentheses is arbitrary within the expression. or Formula (12) below: 【Transformation 3】 [In the formula: R ４ Each of these is independently a hydrogen atom or a monovalent organic group; R ５ Each of these is independently a hydrogen atom or a monovalent organic group; However, R ４ and R ５ At least one of them is a base represented by formula (2); d is an integer greater than or equal to 1. A polyorganosiloxane represented by [a specific symbol / method].

2. The polyorganosiloxane according to claim 1, wherein a is an integer between 10 and 1,000.

3. In equation (11), R １ , R ２ , R ４ , R ５ , R ６ and R ７ At least one of them is equation (2): 【Chemistry 4】 [In the formula: X １ is a hydrogen atom or a protecting group; Y １ These are single bonds or divalent to decavalent organic groups; n1 is an integer greater than or equal to 2. It is a base represented by, Among the other groups, R １ , R ２ , R ４ , R ５ and R ６ Each of these is independently a monovalent organic group that does not contain a hydrogen atom or a group represented by formula (2), R ７ Each of them is independent of R Ｓｉ’ Or a monovalent organic group that does not contain the group represented by formula (2), A monovalent organic group that does not contain the group represented by formula (2) above is C １－２０ Alkyl groups, groups having aryl groups, carbon-carbon double bonds, groups having phenyl groups, SiR １１ ３ -C １－２０ Alkylene group - or Rf-Z-C １－２０ It is an alkylene group. R １１ Each of them is independent of C １－２０ It is an alkyl group, Rf is a C having at least one fluorine atom. １－１６ It is an alkyl group, Z is O, C(=O)NR ９ , NR ９ C(=O), C(=O)O, OC(=O), NR ９ C(=O)O, OC(=O)NR ９ , or NR ９ C(=O)NR ９ And, R ９ Each of these is independently a hydrogen atom, a phenyl group, or C １－６ It is an alkyl group. The polyorganosiloxane according to claim 1.

4. In equation (11), R １ and R ２ At least one of them is equation (2): 【Transformation 5】 [In the formula: X １ is a hydrogen atom or a protecting group; Y １ These are single bonds or divalent to decavalent organic groups; n1 is an integer greater than or equal to 2. The base represented by The polyorganosiloxane according to claim 1.

5. The polyorganosiloxane of formula (11) is given by formula (13): 【Transformation 6】 It is represented as, In formula (13): R １ , R ２ , R ６ and R Ｓｉ These are equivalent to the above; R ４１ Each of these is independently a hydrogen atom, or C １－２０ It is an alkyl group; R ５１ Each of these is independently a hydrogen atom, or C １－２０ It is an alkyl group; R ４２ These are, independently, a group having an aryl group, a group having a carbon-carbon double bond, and SiR １１ ３ -C １－２０ Alkylene group - or Rf-Z-C １－２０ It is an alkylene group; R １１ Each of them is independent of C １－２０ It is an alkyl group; Rf is a C having at least one fluorine atom. １－１６ It is an alkyl group; Z is O, C(=O)NR ９ , NR ９ C(=O), C(=O)O, OC(=O), NR ９ C(=O)O, OC(=O)NR ９ , or NR ９ C(=O)NR ９ And; R ９ Each of these is independently a hydrogen atom, a phenyl group, or C １－６ It is an alkyl group; R ５２ is, independently of each other, a hydrogen atom, C １－２０ alkyl group, a group having an aryl group, a group having a carbon-carbon double bond, a group having a phenyl group, SiR １１ ３ -C １－２０ alkylene group-, or Rf-Z-C １－２０ alkylene group-; R ４３ These are, independently, equation (2): 【Transformation 7】 It is a base represented by; X １ is a hydrogen atom or a protecting group; Y １ These are single bonds or divalent to decavalent organic groups; n1 is an integer greater than or equal to 2; R ５３ is, independently of each other, a hydrogen atom, C １－２０ alkyl group or a group represented by the formula (2); a1 is a non-negative integer; a2 is a non-negative integer; a3 is an integer greater than or equal to 1; However, the sum of a1, a2, and a3 is a; a is 10 or more; b and c are equivalent to the above; The order in which the repeating units a1, a2, a3, b, and c are enclosed in parentheses is arbitrary within the formula. The polyorganosiloxane according to claim 1.

6. In equation (12), R ４ and R ５ Of these, at least one is a group represented by formula (2), and the other groups are, independently of each other, a hydrogen atom, C １－２０ Alkyl groups, groups having aryl groups, carbon-carbon double bonds, groups having phenyl groups, SiR １１ ３ -C １－２０ Alkylene group - or Rf-Z-C １－２０ It is an alkylene group. R １１ Each of them is independent of C １－２０ It is an alkyl group, Rf is a C having at least one fluorine atom. １－１６ It is an alkyl group, Z is O, C(=O)NR ９ , NR ９ C(=O), C(=O)O, OC(=O), NR ９ C(=O)O, OC(=O)NR ９ , or NR ９ C(=O)NR ９ And, R ９ Each of these is independently a hydrogen atom, a phenyl group, or C １－６ It is an alkyl group. The polyorganosiloxane according to claim 1.

7. The polyorganosiloxane according to claim 1, wherein d is an integer between 10 and 1,000.

8. Y １ Each of them is independent of -(R ９１ ) ｐ１ - (X ａ ) ｑ１ -R ９２ It is represented by -, R ９１ is a single bond, -(CH ２ ) ｐ２ - or o-, m- or p-phenylene group, p2 is an integer between 1 and 20. X ａ is, -(X ｂ ) ｑ２ - represents, X ｂ These are, independently, -O-, -S-, o-, m- or p-phenylene groups, -(OR ９５ ) ｐ４ -, -C(O)O-, -Si(R ９３ ) ２ -, -(Si(R ９３ ) ２ O) ｐ５ -Si(R ９３ ) ２ -, -CONR ９４ -, -O-CONR ９４ -, -NR ９４ - and - (CH ２ ) ｐ６ - represents a group selected from the group consisting of, R ９３ Each of these independently consists of a phenyl group and a C １－６ Alkyl alkyl group or C １－６ Represents an alkoxy group, R ９４ Each of these is independently a hydrogen atom, a phenyl group, or C １－６ Represents an alkyl group, R ９５ Each of them is independent of C １－６ It is an alkylene group, p4 are each an independent integer between 1 and 5. p5 are each an independent integer between 1 and 100. p6 are each an integer between 1 and 20, independently of each other. q2 is an integer between 1 and 10. p1 is either 0 or 1. q1 is either 0 or 1. The order of existence of each repeating unit, which is denoted as p1 or q1 and enclosed in parentheses, is arbitrary. Here, at least one of p1 and q1 is 1, R ９２ is a single bond, -(CH ２ ) ｐ３ Represents a - or o-, m- or p-phenylene group, p3 is an integer between 1 and 20. The polyorganosiloxane according to claim 1.

9. Y １ The polyorganosiloxane according to claim 1, wherein the group is not represented by -NHC(=O)-.

10. Y １ The polyorganosiloxane according to claim 1, which does not contain esters, secondary amines, amides, ethers, thioethers, or thioesters.

11. Y １ is, -CH ２ The polyorganosiloxane according to claim 1, which does not contain a group represented by -N=CH-.

12. Y １ C １－２０ The polyorganosiloxane according to claim 1, wherein the group is alkylene.

13. The polyorganosiloxane according to claim 1, wherein n1 is 3 or greater.

14. A polyorganosiloxane according to claim 1, which does not contain a fluorine atom.

15. The polyorganosiloxane according to claim 1, represented by any of the following: [In the formula, n is 34.] [In the formula, n = 34.] [In the equation, x = 27, y = 2, and z = 1.]

16. A composition comprising the polyorganosiloxane described in claim 1.

17. The composition according to claim 16, further comprising a solvent.

18. The composition according to claim 17, wherein the solvent is an organic solvent.

19. The composition according to claim 17, wherein the solvent is an aqueous medium.

20. Furthermore, the composition according to claim 16, further comprising an emulsifier.

21. Furthermore, the composition according to claim 20, comprising an aqueous medium.

22. Furthermore, the composition according to claim 16, further comprising an additive.

23. The composition according to claim 16, comprising a catalyst, a crosslinking agent, a thickening agent, or a pH adjuster.

24. Furthermore, the composition according to claim 23, comprising an organic solvent.

25. Furthermore, the composition according to claim 23, comprising an aqueous medium.

26. The composition according to claim 16, which is a mold release agent or a water-repellent and oil-repellent agent.

27. A molding method for processing a molding material using a mold, A molding method wherein the mold is surface-treated using the composition described in claim 16.

28. The molding method according to claim 27, wherein the molding material is a thermosetting resin.

29. The molding method according to claim 28, wherein the thermosetting resin is a carbon fiber composite material.

Images