Hardening composition

Abstract

To provide a curable composition excellent in adhesion.SOLUTION: The curable composition contains a component (A): a fluoropolyether group-containing compound, a component (B): a (meth)acrylic monomer, and a component (C): a radical polymerization initiator. The fluoropolyether group-containing compound contains at least one compound represented by the following formula (A1) or (A2).SELECTED DRAWING: None

Description

Technical Field

[0001] The present disclosure relates to a curable composition containing a fluorine-containing compound.

Background Art

[0002] Compositions containing certain fluorine-containing compounds are known to give cured products having excellent water repellency, oil repellency, stain resistance, etc. (Patent Documents 1 and 2).

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0004] An object of the present disclosure is to provide a curable composition having excellent adhesion.

Means for Solving the Problems

[0005] The present disclosure includes the following aspects. [1] Component (A): a fluoropolyether group-containing compound, Component (B): a (meth)acrylic monomer, and Component (C): a radical polymerization initiator containing wherein the fluoropolyether group-containing compound is represented by the following formula (A1) or (A2):

Chemical Formula

Chemical formula

[10] R 5 The curable composition according to any one of the above [1] to [9], wherein represents a hydrogen atom or a methyl group.

[11] X A are each independently a single bond, or -(C α R 11 2α ) s1 -R 12 t1 - [In formula: R 11 are each independently a hydrogen atom or a fluorine atom, Each a is independently an integer from 1 to 10, R 12 are each independently -O-, -CO-, or -NR 10 -,-CONR 10 -, -NR 10is CO-, -COO-, -OCO-, or -OCONH- R 10 is a hydrogen atom or C 1-6 alkyl group, s1 is an integer from 0 to 3, t1 is an integer from 0 to 3, the sum of s1 and t1 is 1 or more, the order of existence of each repeating unit enclosed in parentheses with s1 or t1 attached is arbitrary in the formula.] The curable composition according to any one of the above [1] to

[10] , which is a group represented by

[12] X A is -CONR 10 -C α1 H 2α1 -, -(C α2 H 2α2 )-OCONR 10 -, -(C α3 H 2α3 )-, or -(C α4 H 2α4 )-O-(C α5 H 2α5 ) and R 10 is a hydrogen atom or C 1-6 alkyl group, α1 is an integer from 1 to 10, α2 is an integer from 1 to 10, α3 is an integer from 1 to 10, α4 is an integer from 0 to 6, α5 is an integer from 0 to 6, The curable composition according to any one of the above [1] to

[10] .

[13] X B are each independently SiR 1 nb R sb 4-nb [wherein: R 1 is a hydroxyl group or a hydrolyzable group, R sb is a single bond, nb is 1 or 2.] a group containing a group represented by The curable composition according to any one of [1] to

[12] above.

[14] X B each independently, X Ba (R Si ) na [wherein: X Ba each independently, is a (m + na + 1)-valent group, R Si each independently, is -X C -SiR 1 n’ R 2 3-n’ and X C is a divalent organic group having 1 to 10 carbon atoms, R 1 each independently, is a hydroxyl group or a hydrolyzable group, R 2 each independently, is a hydrogen atom or a monovalent organic group, n’ is an integer of 1 to 3, na is an integer of 1 to 10.] The curable composition according to any one of [1] to

[12] above, which is a group represented by

[15] X C is C 1-6 an alkylene group, -(CH2) z1 -O-(CH2) z2 -(wherein, z1 is an integer of 0 to 6, and z2 is an integer of 0 to 6), -(CH2) z3 -phenylene-(CH2) z4 -(wherein, z3 is an integer of 0 to 6, and z4 is an integer of 0 to 6), or -(CH2) z13 -OCONH-(CH2) z14 -(wherein, z13 is an integer of 0 to 6, and z14 is an integer of 0 to 6) The curable composition according to

[14] above, which is

[16] The curable composition according to

[14] above, wherein n' is 3.

[17] X Ba

[14] The curable composition according to the above

[14] , wherein: is a trivalent group, n is 1, and m is 1.

[18] X Ba is N or —C(—O—)—, n is 1, and m is 1.

[19] Equation (A2) is [ka] [In the formula, R b are each independently R Si , R Ac , or R c and However, R b At least one of the Si and R Si are each independently -X C -SiR 1 n’ R 2 3-n’ and X C is a divalent organic group having 1 to 10 carbon atoms, R 1 are each independently a hydroxyl group or a hydrolyzable group, R 2 are each independently a hydrogen atom or a monovalent organic group, n' is an integer from 1 to 3, R d are each independently a single bond or a divalent organic group, R F2 , R a , R c , R Ac , m3, and x are defined as in [1] above.] The curable composition according to any one of the above [1] to

[18] , wherein

[20] R bonded to the N atom at each end in formula (A2) b One of them is R Siand the other is R c or R Ac The curable composition according to

[19] above,

[21] R d are each independently a single bond or -(CH2) z17 -NR 10 -(CH2) z18 -(In the formula, R 10 is a hydrogen atom or C 1-6 z17 is an integer of 0 to 6, and z18 is an integer of 0 to 6).

[22] R a are each independently represented by the following formula: -R 9 -(R a’ -R 9 ) k - [In formula: R 9 are each independently 1-6 is an alkylene group, R a’ are each independently a trivalent group, k is an integer from 1 to 4. The curable composition according to any one of the above [1] to

[21] , wherein the group is represented by the following formula:

[23] R a’ are each independently N, —C(—O—)—, or a trivalent group which may contain an amino bond, an amide bond, a urethane bond, a urea bond, an ether bond, or an ester bond between carbon atoms.

[24] The curable composition according to

[22] above, wherein k is 1 or 2.

[25] R c are each independently a hydrogen atom or C 1-6 The curable composition according to any one of the above [1] to

[24] , wherein the group is an alkyl group.

[26] The curable composition according to any one of the above [1] to

[25] , wherein x is an integer of 1 or more and 5 or less.

[27] The curable composition according to any one of the above [1] to

[26] , wherein the fluoropolyether group-containing compound comprises a compound represented by formula (A1).

[28] The curable composition according to any one of the above [1] to

[26] , wherein the fluoropolyether group-containing compound comprises a compound represented by formula (A2).

[29] The curable composition according to any one of the above [1] to

[28] , wherein the (meth)acrylic monomer is (a) a urethane (meth)acrylate, (b) an epoxy (meth)acrylate, (c) a polyester (meth)acrylate, (d) a polyether (meth)acrylate, (e) a silicon (meth)acrylate, or (f) a (meth)acrylate monomer.

[30] The curable composition according to any one of the above [1] to

[29] , wherein the radical polymerization initiator is a diketone, an acyloin, an acyloin ether, a thioxanthone, a benzophenone, an acetophenone, a quinone, an aminobenzoic acid, a halogen compound, an acylphosphine oxide, or a peroxide.

[31] The radical polymerization initiator may be benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, thioxanthone, 2,4-diethylthioxanthone, thioxanthone-4-sulfonic acid, benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, acetophenone, 2-(4-toluenesulfonyloxy)-2-phenylacetophenone, p-dimethylaminoacetophenone, 2,2'-dimethoxy-2-phenylacetophenone, p-Methoxyacetophenone, 2-methyl[4-(methylthio)phenyl]-2-morpholino-1-propanone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, anthraquinone, 1,4-naphthoquinone, ethyl 2-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, (n-butoxy)ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, phenacyl chloride, trihalomethylphenyl sulfone , acylphosphine oxide, or di-t-butyl peroxide, methyl benzoyl formate, 1-hydroxy-cyclohexyl-phenyl-ketone, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]phenyl}-2-methyl-propan-1-one, 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one, 2-benzyl-2-dimethyl arylamino-1-(4-morpholinophenyl)-1-butanone, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, bis(η5-2,4-cyclopentadien-1-yl)-bis(2,6-difluoro-3-(1H-pyrrol-1-yl)-phenyl)titanium, 1,2-octanedione, 1-[4-(phenylthio)-, 2-(O-benzoyloxime)], ethanone,The curable composition according to any one of the above [1] to

[30] , which is 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-,1-(0-acetyloxime), 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide, t-butyl hydroperoxide, cumene hydroperoxide, diisopropylbenzene hydroperoxide, permentha hydroperoxide, or t-methylbutyl hydroperoxide.

[32] The curable composition according to any one of the above [1] to

[31] , further comprising a solvent.

[33] A cured product obtained from the curable composition according to any one of the above [1] to

[32] .

[34] An article comprising a substrate and a layer formed on the surface of the substrate from the curable composition according to any one of the above [1] to

[32] . [Effects of the Invention]

[0006] According to the present disclosure, it is possible to provide a curable composition having excellent adhesion. DETAILED DESCRIPTION OF THE INVENTION

[0007] As used herein, the term "monovalent organic group" refers to a monovalent group containing carbon. The monovalent organic group is not particularly limited, but may be a hydrocarbon group or a derivative thereof. A hydrocarbon group derivative refers to a group having one or more N, O, S, Si, amide, sulfonyl, siloxane, carbonyl, carbonyloxy, etc. at the end or in the molecular chain of the hydrocarbon group. Note that when simply referring to an "organic group," it refers to a monovalent organic group. Furthermore, the term "divalent organic group" refers to a divalent group containing carbon. Examples of such divalent organic groups include divalent groups in which one additional hydrogen atom has been eliminated from an organic group. Similarly, a trivalent or higher organic group refers to a group in which a predetermined number of hydrogen atoms have been eliminated from an organic group.

[0008] As used herein, the term "hydrocarbon group" refers to a group containing carbon and hydrogen, which is obtained by removing a hydrogen atom from a hydrocarbon. Such hydrocarbon groups include, but are not limited to, C 1-20 Examples of hydrocarbon groups include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The "aliphatic hydrocarbon group" may be linear, branched, or cyclic, and may be saturated or unsaturated. The hydrocarbon group may contain one or more ring structures. The hydrocarbon group may be substituted with one or more substituents.

[0009] As used herein, the substituent of the "hydrocarbon group" is not particularly limited, but examples thereof include a halogen atom, a C 1-6 Alkyl group, C 2-6 Alkenyl group, C 2-6 Alkynyl group, C 3-10 Cycloalkyl groups, C 3-10 Unsaturated cycloalkyl groups, 5-10 membered heterocyclyl groups, 5-10 membered unsaturated heterocyclyl groups, C 6-10 Examples include one or more groups selected from aryl groups and 5- to 10-membered heteroaryl groups.

[0010] As used herein, the term "hydrolyzable group" refers to a group that can undergo a hydrolysis reaction, i.e., a group that can be removed from the main skeleton of a compound by a hydrolysis reaction. Examples of hydrolyzable groups include -OR j , -OCOR j , -ON=CR j 2, -NR j 2, -NHR j , —NCO, —NCO, or halogen (wherein R j is a substituted or unsubstituted C 1-4 (representing an alkyl group) and the like.

[0011] The curable composition of the present disclosure comprises: Component (A): fluoropolyether group-containing compound, Component (B): (meth)acrylic monomer, and Component (C): Radical polymerization initiator Includes.

[0012] Component (A): Fluoropolyether group-containing compound

[0013] The fluoropolyether group-containing compound contained in the curable composition of the present disclosure contains a (meth)acrylic group, a hydrolyzable silane group, and a fluoropolyether group. The curable composition of the present disclosure has excellent curability due to the inclusion of the fluoropolyether group-containing compound. In this specification, (meth)acrylic includes acrylic and methacrylic.

[0014] The fluoropolyether group-containing compound is represented by the following formula (A1) or (A2): [ka] [In formula: R F2 are each independently -Rf 2 p -R F -O q - and Rf 2 C optionally substituted with one or more fluorine atoms 1-6 is an alkylene group, R F are each independently a divalent fluoropolyether group; p is 0 or 1; Each q is independently 0 or 1; X A are each independently a single bond or a divalent organic group, X B are each independently an (m+1)-valent group, However, in each formula, at least one X B is an (m+1)-valent group containing a hydrolyzable silyl group, R Ac are each independently -X D -XE (-X F -OCO-CR 5 =CH2) m’ and X D is a single bond or a divalent group, X E is a single bond or an (m'+1)-valent group, X F are each independently a single bond or a divalent group, R 5 is a hydrogen atom, a halogen atom, or a monovalent organic group having 1 to 8 carbon atoms, m' is an integer from 1 to 10, m is independently an integer of 0 to 10, R a are each independently an (m3+2)-valent organic group, m3 is an integer from 0 to 4, However, at least one of m and m3 is 1 or more, R g are each independently -NR c CO-R e -, -NR c COO-R e - or -NR c CONR c -R e -, where these groups are represented by R a binds to R c are each independently a hydrogen atom, C 1-6 Alkyl group or C 6-16 is an aryl group, R e are each independently a single bond or a divalent organic group, x is an integer greater than or equal to 1. The compound includes at least one of the compounds represented by the following formula (1):

[0015] The fluoropolyether group-containing compound preferably contains a (meth)acrylic group and a hydrolyzable silane group at both ends thereof. B is a group containing a hydrolyzable silyl group.

[0016] In one aspect, the fluoropolyether group-containing compound includes a compound represented by formula (A1). For example, the fluoropolyether group-containing compound is a compound represented by formula (A1).

[0017] In one aspect, the fluoropolyether group-containing compound includes a compound represented by formula (A2). For example, the fluoropolyether group-containing compound is a compound represented by formula (A2).

[0018] In one aspect, the fluoropolyether group-containing compound includes a compound represented by formula (A1) and a compound represented by formula (A2). For example, the fluoropolyether group-containing compound is a compound represented by formula (A1) and a compound represented by formula (A2). <s

[0019] In the above formulas (A1) and (A2), R F2 is -Rf 2 p -R F -O q -.

[0020] In the above formula, Rf 2 is each independently a C alkylene group which may be substituted by one or more fluorine atoms. 1-6

[0021] The "C alkylene group" in the C alkylene group which may be substituted by one or more fluorine atoms may be linear or branched, preferably a linear or branched C alkylene group, more preferably a linear C alkylene group. 1-6 1-6 1-3 1-3 2 1-6 1-6

[0022] The above Rf 2 is preferably a C alkylene group substituted by one or more fluorine atoms, more preferably a C 1-6 alkylene group 1-6 ​is a perfluoroalkylene group, more preferably a C 1-3 perfluoroalkylene group.

[0023] The above C 1-6 perfluoroalkylene group may be linear or branched, preferably a linear or branched C 1-3 perfluoroalkylene group, more preferably a linear C 1-3 perfluoroalkyl group, specifically -CF2-, -CF2CF2-, or -CF2CF2CF2-.

[0024] In the above formula, p is 0 or 1. In one embodiment, p is 0. In another embodiment, p is 1.

[0025] In the above formula, q is independently 0 or 1 respectively. In one embodiment, q is 0. In another embodiment, q is 1.

[0026] In the above formulas (A1) to (A2), R F are each independently a divalent fluoropolyether group.

[0027] R F is preferably a linear divalent fluoropolyether group. By using a linear divalent fluoropolyether group, the viscosity is relatively low, and the coating property and handling property are improved.

[0028] R F is preferably of the formula: -(OC6F 12 ) a -(OC5F 10 ) b -(OC4F8) c -(OC3R Fa 6) d -(OC2F4) e -(OCF2) f - [wherein: R Fa are each independently a hydrogen atom, a fluorine atom or a chlorine atom, a, b, c, d, e, and f each independently represent an integer of 0 to 200, and the sum of a, b, c, d, e, and f is 1 or more. The order of the repeating units enclosed in parentheses with a, b, c, d, e, or f is arbitrary in the formula. However, all R Fa is a hydrogen atom or a chlorine atom, at least one of a, b, c, e, and f is 1 or greater.] It is a group represented by the following formula:

[0029] R Fa is preferably a hydrogen atom or a fluorine atom, more preferably a fluorine atom. Fa is a hydrogen atom or a chlorine atom, at least one of a, b, c, e and f is 1 or greater.

[0030] Preferably, a, b, c, d, e and f may each independently be an integer of 0 to 100.

[0031] The sum of a, b, c, d, e, and f is preferably 5 or more, more preferably 10 or more, and may be, for example, 15 or more or 20 or more. The sum of a, b, c, d, e, and f is preferably 200 or less, more preferably 100 or less, and even more preferably 60 or less, and may be, for example, 50 or less or 30 or less.

[0032] These repeating units may be linear or branched, and may contain a ring structure. For example, -(OCF 12 )- may be -(OCF2CF2CF2CF2CF2CF2CF2)-, -(OCF(CF3)CF2CF2CF2CF2)-, -(OCF2CF(CF3)CF2CF2CF2)-, -(OCF2CF2CF(CF3)CF2CF2)-, -(OCF2CF2CF2CF(CF3)CF2)-, -(OCF2CF2CF2CF2CF(CF3)CF2)-, -(OCF2CF2CF2CF2CF(CF3))-, etc. 10)- may be, for example, -(OCF2CF2CF2CF2CF2)-, -(OCF(CF3)CF2CF2CF2)-, -(OCF2CF(CF3)CF2CF2)-, -(OCF2CF2CF(CF3)CF2)-, -(OCF2CF2CF2CF(CF3))-, etc. -(OC4F8)- may be any of -(OCF2CF2CF2CF2)-, -(OCF(CF3)CF2CF2)-, -(OCF2CF(CF3)CF2)-, -(OCF2CF2CF(CF3))-, -(OC(CF3)2CF2)-, -(OCF2C(CF3)2)-, -(OCF(CF3)CF(CF3))-, -(OCF(C2F5)CF2)-, and -(OCF2CF(C2F5))-. -(OC3F6)- (i.e., in the above formula, R Fa is a fluorine atom) may be any of -(OCF2CF2CF2)-, -(OCF(CF3)CF2)-, and -(OCF2CF(CF3))-. -(OC2F4)- may be any of -(OCF2CF2)- and -(OCF(CF3))-.

[0033] The above ring structure may be a three-membered ring, four-membered ring, five-membered ring, or six-membered ring as follows. [Chemical formula] [In the formula, * indicates the bonding position.]

[0034] The above ring structure may preferably be a four-membered ring, five-membered ring, or six-membered ring, more preferably a four-membered ring or six-membered ring.

[0035] The repeating unit having a ring structure may preferably be the following unit. [Chemical formula] [In the formula, * indicates the bonding position.]

[0036] In one aspect, the above repeating unit is linear. By making the above repeating unit linear, the durability of the cured product layer and the like can be improved.

[0037] In one embodiment, the repeating unit is branched.

[0038] In one embodiment, R F is, independently of one another, a group represented by any of the following formulas (f1) to (f6). -(OC3F6) d -(OC2F4) e - (f1) [wherein d is an integer of 1 to 200, and e is 0 or 1, preferably 1.]; -(OC4F8) c -(OC3F6) d -(OC2F4) e -(OCF2) f - (f2) [wherein c and d are each independently an integer of 0 or more and 30 or less, e and f are each independently an integer of 1 or more and 200 or less, the sum of c, d, e and f is 2 or more, the order of presence of each repeating unit enclosed in parentheses with a subscript c, d, e or f is arbitrary in the formula.]; -(R 6 -R 7 ) g - (f3) [wherein R 6 is OCF2 or OC2F4, R 7 is a group selected from OC2F4, OC3F6, OC4F8, OC5F 10 and OC6F 12 or a combination of two or three groups independently selected from these groups, and g is an integer of 2 to 100.]; -(R 6 -R 7 ) g -R r -(R 7’ -R 6’ ) g’ - (f4) [wherein R 6 is OCF2 or OC2F4, R 7are OC2F4, OC3F6, OC4F8, OC5F 10 and OC6F 12 or a combination of two or three groups independently selected from these groups, R 6’ is OCF2 or OC2F4, R 7’ are OC2F4, OC3F6, OC4F8, OC5F 10 and OC6F 12 or a combination of two or three groups independently selected from these groups, g is an integer from 2 to 100, g' is an integer from 2 to 100, R r teeth, [ka] (In the formula, * indicates the bonding position.) ]; -(OC6F 12 ) a -(OC5F 10 ) b -(OC4F8) c -(OC3F6) d -(OC2F4) e -(OCF2) f - (f5) [In the formula, e is an integer of 1 or more and 200 or less, a, b, c, d, and f are each independently an integer of 0 or more and 200 or less, and the order of the repeating units enclosed in parentheses with a, b, c, d, e, or f is arbitrary in the formula.] -(OC6F 12 ) a -(OC5F 10 ) b -(OC4F8) c -(OC3F6) d -(OC2F4) e -(OCF2) f - (f6) [In the formula, f is an integer of 1 or more and 200 or less, and a, b, c, d, and e are each independently an integer of 0 or more and 200 or less. Also, the order of existence of each repeating unit enclosed in parentheses with a, b, c, d, e, or f attached is arbitrary in the formula.]

[0039] In the above formula (f1), d is preferably an integer of 5 to 200, more preferably 10 to 100, still more preferably 15 to 50, for example, 25 to 35. In one embodiment, e is 1. In another embodiment, e is 0. (OC3F6) in the above formula (f1) is preferably a group represented by (OCF2CF2CF2), (OCF2CF(CF3)), or (OCF(CF3)CF2), more preferably, - (OCF2CF2CF2) d is a group represented by -. (OC2F4) in the above formula (f1) is preferably a group represented by (OCF2CF2) or (OCF(CF3)), more preferably a group represented by (OCF2CF2).

[0040] In the above formula (f2), e and f are each independently preferably an integer of 5 to 200, more preferably 10 to 200. Also, the sum of c, d, e, and f is preferably 5 or more, more preferably 10 or more, and may be, for example, 15 or more or 20 or more. In one embodiment, the above formula (f2) is preferably - (OCF2CF2CF2CF2) c - (OCF2CF2CF2) d - (OCF2CF2) e - (OCF2) f is a group represented by -. In another embodiment, the formula (f2) may be - (OC2F4) e - (OCF2) f is a group represented by -.

[0041] In the above formula (f3), R 6 is preferably OC2F4. In the above (f3), R 7is preferably a group selected from OC2F4, OC3F6 and OC4F8, or a combination of two or three groups independently selected from these groups, more preferably a group selected from OC3F6 and OC4F8. The combination of two or three groups independently selected from OC2F4, OC3F6 and OC4F8 is not particularly limited, and examples thereof include -OC2F4OC3F6-, -OC2F4OC4F8-, -OC3F6OC2F4-, -OC3F6OC3F6-, -OC3F6OC4F8-, -OC4F8OC4F8-, -OC4F8OC3F6-, -OC4F8OC2F4-, -OC Examples include 2F4OC2F4OC3F6-, -OC2F4OC2F4OC4F8-, -OC2F4OC3F6OC2F4-, -OC2F4OC3F6OC3F6-, -OC2F4OC4F8OC2F4-, -OC3F6OC2F4OC2F4-, -OC3F6OC2F4OC2F4-, -OC3F6OC2F4OC3F6-, -OC3F6OC3F6OC2F4-, and -OC4F8OC2F4OC2F4-. In the above formula (f3), g is preferably an integer of 3 or more, more preferably 5 or more. The above g is preferably an integer of 50 or less. In the above formula (f3), OC2F4, OC3F6, OC4F8, OC5F 10 and OC6F 12 may be either a straight chain or a branched chain, and is preferably a straight chain. In this embodiment, the above formula (f3) is preferably -(OC2F4-OC3F6) g -or-(OC2F4-OC4F8) g -It is.

[0042] In the above formula (f4), R 6 , R 7 and g have the same meanings as those in the formula (f3) above, and have the same embodiments. 6’ , R 7’ and g' are R 6 , R 7 and g have the same meaning and similar aspects. r is preferably [ka] [In the formula, * indicates the bonding position.] and more preferably [Chemical formula] [In the formula, * indicates the bonding position.] is.

[0043] In the above formula (f5), e is preferably an integer of 1 or more and 100 or less, more preferably 5 or more and 100 or less. The sum of a, b, c, d, e and f is preferably 5 or more, more preferably 10 or more, for example, 10 or more and 100 or less.

[0044] In the above formula (f6), f is preferably an integer of 1 or more and 100 or less, more preferably 5 or more and 100 or less. The sum of a, b, c, d, e and f is preferably 5 or more, more preferably 10 or more, for example, 10 or more and 100 or less.

[0045] In one embodiment, the above R F is a group represented by the above formula (f1) or (f2).

[0046] In one embodiment, the above R F is a group represented by the above formula (f1).

[0047] In one embodiment, the above R F is a group represented by the above formula (f2).

[0048] In one embodiment, the above R F is a group represented by the above formula (f3) or (f4).

[0049] In one embodiment, the above R F is a group represented by the above formula (f3).

[0050] In one embodiment, the above R F is a group represented by the above formula (f4).

[0051] In one embodiment, the above RF is a group represented by the above formula (f5).

[0052] In one aspect, the above R F is a group represented by the above formula (f6).

[0053] In the above R F the ratio of e to f (hereinafter referred to as "e / f ratio") is 0.1 to 10, preferably 0.2 to 5, more preferably 0.2 to 2, still more preferably 0.2 to 1.5, and even more preferably 0.2 to 0.85. By setting the e / f ratio to 10 or less, the durability and chemical resistance (for example, durability against artificial sweat) of the cured product layer obtained from this compound are further improved. The smaller the e / f ratio, the more improved the durability and chemical resistance of the cured product layer. On the other hand, by setting the e / f ratio to 0.1 or more, the stability of the compound can be further enhanced. The larger the e / f ratio, the more improved the stability of the compound.

[0054] In one aspect, the above e / f ratio is preferably 0.2 to 0.95, more preferably 0.2 to 0.9.

[0055] In one aspect, from the viewpoint of heat resistance, the above e / f ratio is preferably 1.0 or more, more preferably 1.0 to 2.0.

[0056] In the above fluoropolyether group-containing compound, R F2 The number average molecular weight of the part is not particularly limited, but is, for example, 500 to 30,000, preferably 1,500 to 30,000, more preferably 2,000 to 10,000. In this specification, the number average molecular weight of R F2 is 19 a value measured by 19F-NMR.

[0057] In the above formulas (A1) and (A2), R Ac are each independently -X D -X E (-X F -OCO-CR5 =CH2) m’ is.

[0058] Above X D is a single bond or a divalent group, for example a divalent organic group.

[0059] X D is preferably —O—, —CO—, —COO—, —OCO—, —CONH—, —NHCO—, —OCONH—, —NHCOO—, —NH—CO—NH—, —CHCH(OH)CH—, —CH(CHOH)CH—, —(OSiR 14 2) d5 -, [ka] [In the formula, * and ** indicate bonding positions, * indicates X B , and ** is X E Binds to.] and R 14 is C 1-6 Alkyl group or C 6-16 is an aryl group, d5 is an integer from 1 to 10. These groups are B Combine with.

[0060] X D is more preferably -CONH-, -CH2CH(OH)CH2-, or -CH(CH2OH)CH2-, more preferably -CONH-.

[0061] Above X E is a single bond or an (m'+1)-valent group.

[0062] In one embodiment, X E is a single bond.

[0063] In one embodiment, X E teeth, -X G -X H [In formula: X Gis a single bond, C 1-6 an alkylene group, -(CH2) z9 -O-(CH2) z10 -(wherein, z9 is an integer from 0 to 6, for example, an integer from 1 to 6, and z10 is an integer from 0 to 6, for example, an integer from 1 to 6), or -(CH2) z11 -phenylene-(CH2) z12 -(wherein, z11 is an integer from 0 to 6, for example, an integer from 1 to 6, and z12 is an integer from 0 to 6, for example, an integer from 1 to 6) and X H is as follows

Chemical formula

[0064] The above C 1-6 alkylene group may be linear or branched, but is preferably linear.

[0065] In a preferred embodiment, the above C 1-6 alkylene group is a C 2-4 alkylene group.

[0066] The above C 1-6 alkyl group is preferably a C 1-3 alkyl group, more preferably a methyl group.

[0067] The above X F is each independently a single bond, or a divalent group, for example, a divalent organic group (preferably a divalent organic group having 1 to 10 carbon atoms).

[0068] In one embodiment, X F is a single bond, C 1-6An alkylene group, -(CH2) z5 -O-(CH2) z6 -(wherein, z5 is an integer of 0 to 6, for example, an integer of 1 to 6, and z6 is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z7 -phenylene-(CH2) z8 -(wherein, z7 is an integer of 0 to 6, for example, an integer of 1 to 6, and z8 is an integer of 0 to 6, for example, an integer of 1 to 6) is. These groups are, for example, a fluorine atom, C 1-6 alkyl group, C 2-6 alkenyl group, and C 2-6 alkynyl group, and may be substituted with one or more substituents selected therefrom, but is preferably unsubstituted. These groups are bonded to X B on the left side.

[0069] The above C 1-6 alkylene group may be linear or branched, but is preferably linear.

[0070] In a preferred embodiment, X F is a C 1-6 alkylene group, preferably a C 2-4 alkylene group.

[0071] In one embodiment, X D , X E , and X F are single bonds.

[0072] The above R 5 is a hydrogen atom, a halogen atom, or a monovalent organic group having 1 to 8 carbon atoms.

[0073] The above monovalent organic group is preferably a C 1-8 alkyl group, a C 3-8 cycloalkyl group, or a C 5-8 aryl group, more preferably a C 1-6 alkyl group or a phenyl group, and even more preferably a C 1-3It is an alkyl group, particularly preferably a methyl group.

[0074] In one embodiment, R 5 is a hydrogen atom.

[0075] In one embodiment, R 5 is a methyl group.

[0076] The above m' is an integer from 1 to 10, preferably an integer from 1 to 3, more preferably 1.

[0077] In the above formulas (A1) and (A2), X A is each independently a single bond or a divalent organic group.

[0078] In one embodiment, X A is each independently a single bond or a divalent organic group that does not contain a urethane bond, a polyisocyanate structure, or a siloxane bond.

[0079] In a preferred embodiment, X A is each independently a single bond or -(C α R 11 2α ) s1 -R 12 t1 - [wherein: R 11 is each independently a hydrogen atom or a fluorine atom, α is each independently an integer from 1 to 10, R 12 is each independently -O-, -CO-, -CONH-, -NHCO-, -COO-, -OCO-, or -OCONH-, s1 is an integer from 0 to 3, t1 is an integer from 0 to 3, the sum of s1 and t1 is 1 or more, the order of existence of each repeating unit enclosed in parentheses with s1 or t1 is arbitrary in the formula.] In the formula, the left side is R F2 Combine with.

[0080] In one embodiment, X A is a single bond.

[0081] In one embodiment, X A are each independently the above-(C α R 11 2α ) s1 -R 12 t1 -It is.

[0082] Above R 11 is preferably a hydrogen atom.

[0083] The above α's are each independently preferably an integer of 1 to 6, more preferably an integer of 1 to 4, and even more preferably an integer of 2 to 4.

[0084] Above R 12 are each independently preferably -O-, -CO-, or -NR 10 -, -CONH-, or -COO-, more preferably -CONH-.

[0085] Above R 10 is a hydrogen atom or C 1-6 It is an alkyl group, preferably a hydrogen atom.

[0086] The above s1 is preferably an integer of 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0087] The above t1 is preferably an integer of 0 to 2, more preferably 1 or 2, and even more preferably 1.

[0088] In a preferred embodiment, R 11 is a hydrogen atom, α is an integer from 2 to 4, R 12 -O-, -CO-, -NR10 -, -CONH-, or -COO-; R 10 is a hydrogen atom or C 1-6 is an alkyl group, s1 is 1 or 2, t1 is 0 or 1.

[0089] In a more preferred embodiment, X A -CONR 10 -C α1 H 2α1 -, -(C α2 H 2α2 )-OCONR 10 -, -(C α3 H 2α3 )-, or -(C α4 H 2α4 )-O-(C α5 H 2α5 ) and R 10 is a hydrogen atom or C 1-6 is an alkyl group, α1 is an integer from 1 to 10, α2 is an integer from 1 to 10, α3 is an integer from 1 to 10, α4 is an integer from 0 to 6, α5 is an integer from 0 to 6. Such a group has a structure in which the left side is R F2 Combine with.

[0090] X A is preferably -CONH-C α H 2α -. Such groups are those where the left side is R F2 Combine with.

[0091] Above C α1 H 2α1 is preferably (CH2) α1 is.

[0092] Above C α2 H 2α2 is preferably (CH2) α2 is.

[0093] The above C α3 H 2α3 is preferably (CH2) α3 .

[0094] The above C α4 H 2α4 is preferably (CH2) α4 .

[0095] The above C α5 H 2α5 is preferably (CH2) α5 .

[0096] In the above formulas (A1) and (A2), X B is, independently of each other, an (m + 1)-valent group. However, in each formula, at least one X B is an (m + 1)-valent group containing a hydrolyzable silyl group.

[0097] In one embodiment, X B is, independently of each other, an (m + 1)-valent group containing a hydrolyzable silyl group.

[0098] In one embodiment, X B is, independently of each other, SiR 1 nb R sb 4-nb [wherein: R 1 is a hydroxyl group or a hydrolyzable group, R sb is a single bond, nb is 1 or 2.] a group containing a group represented by, or X Ba (R Si ) na [wherein: X Ba is, independently of each other, an (m + na + 1)-valent group, R Si is, independently of each other, -X C -SiR 1n’ R 2 3-n’ is, X C is a divalent organic group having 1 to 10 carbon atoms, R 1 are each independently a hydroxyl group or a hydrolyzable group, R 2 are each independently a hydrogen atom or a monovalent organic group, n’ is an integer of 1 to 3, na is an integer of 1 to 10.] is a group represented by.

[0099] In one embodiment, X B are each independently X Ba (R Si ) na [wherein: X Ba are each independently an (m + na + 1)-valent group, R Si are each independently -X C -SiR 1 n’ R 2 3-n’ is, X C is a divalent organic group having 1 to 10 carbon atoms, R 1 are each independently a hydroxyl group or a hydrolyzable group, R 2 are each independently a hydrogen atom or a monovalent organic group, n’ is an integer of 1 to 3, na is an integer of 1 to 10.] is a group represented by.

[0100] In such an embodiment, formula (A1) is the following formula (A1-a):

Chemical formula

[0101] Above R Si are each independently -X C -SiR 1 n’ R 2 3-n’ is.

[0102] Above X C is a divalent organic group having 1 to 10 carbon atoms.

[0103] In one embodiment, X C teeth, C 1-6 an alkylene group, -(CH2) z1 -O-(CH2) z2 - (wherein z1 is an integer of 0 to 6, for example, an integer of 1 to 6, and z2 is an integer of 0 to 6, for example, an integer of 1 to 6), -(CH2) z3 -phenylene-(CH2) z4 - (wherein z3 is an integer of 0 to 6, for example, an integer of 1 to 6, and z4 is an integer of 0 to 6, for example, an integer of 1 to 6), or -(CH2) z13 -OCONH-(CH2) z14 - (wherein z13 is an integer of 0 to 6, and z14 is an integer of 0 to 6) These groups include, for example, fluorine atoms, C 1-6 Alkyl group, C 2-6 Alkenyl groups, and C 2-6 The alkynyl group may be substituted, but is preferably unsubstituted, by one or more substituents selected from the group consisting of alkynyl groups. B Combine with.

[0104] Above C 1-6 The alkylene group may be straight-chain or branched, but is preferably straight-chain.

[0105] In a preferred embodiment, X C is C 1-6 Alkylene group, preferably C 2-4 It is an alkylene group.

[0106] The above R 1 is, independently of each other, a hydroxyl group or a hydrolyzable group.

[0107] R 1 is preferably, independently of each other, a hydrolyzable group.

[0108] R 1 is preferably, independently of each other, -OR h , -OCOR h , -O-N=CR h 2, -NR h 2, -NHR h , -NCO, or a halogen (in these formulas, R h represents a substituted or unsubstituted C 1-4 alkyl group), and more preferably -OR h (i.e., an alkoxy group). As R h , there may be mentioned unsubstituted alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, and an isobutyl group; and substituted alkyl groups such as a chloromethyl group. Among them, an alkyl group, particularly an unsubstituted alkyl group, is preferable, and a methyl group or an ethyl group is more preferable. In one embodiment, R h is a methyl group, and in another embodiment, R h is an ethyl group.

[0109] The above R 2 is, independently of each other, a hydrogen atom or a monovalent organic group. Such a monovalent organic group is a monovalent organic group excluding the above hydrolyzable group.

[0110] R 2 in, the monovalent organic group is preferably a C 1-20 alkyl group, more preferably a C 1-6 alkyl group, and still more preferably a methyl group.

[0111] In the above formula, n' is (SiR 1 n’ R 2 3-n’) units are each independently an integer of 1 to 3, preferably 2 or 3, and more preferably 3.

[0112] The above na is preferably an integer of 1 to 6, more preferably an integer of 1 to 3, and particularly preferably 1.

[0113] In one embodiment, the X Ba is a trivalent group, preferably [ka] In one embodiment, the —C(—O—)— is O is R Si In another embodiment, -C(-O-)- means that O is R Ac Combine with.

[0114] In a preferred embodiment, X Ba is N, where m is 1 and n is 1.

[0115] In another embodiment, X B are each independently SiR 1 nb R sb 4-nb [In formula: R 1 is a hydroxyl group or a hydrolyzable group, R sb is a single bond, nb is 1 or 2. Preferably, a group containing a group represented by -X Bb -SiR 1 nb R sb 4-nb [In formula: X Bb is a single bond or a divalent group, R 1 is a hydroxyl group or a hydrolyzable group, R sb is a single bond, nb is 1 or 2. It is a group represented by

[0116] In the above formulas (A1) and (A2), m is, independently of each other, an integer of 0 to 10, and n is, independently of each other, an integer of 1 to 10.

[0117] m is preferably an integer of 1 to 10, more preferably an integer of 1 to 6, still more preferably an integer of 1 to 3, and even more preferably 1.

[0118] n is preferably an integer of 1 to 6, more preferably an integer of 1 to 3, and particularly preferably 1.

[0119] In a preferred embodiment, m is 1 and n is 1.

[0120] In the above (A2), R a is, independently of each other, a (m3 + 2)-valent organic group.

[0121] In one embodiment, R a is the following formula: -R 9 -(R a’ -R 9 ) k - [wherein: R 9 is, independently of each other, a C 1-6 alkylene group, R a’ is, independently of each other, a trivalent group, for example, a trivalent organic group, k is an integer of 1 to 4. ] It is a group represented by. In such a group, the above -C(-O-)- is such that O is bonded to R Ac .

[0122] R 9 is preferably a C 1-4 alkylene group, and more preferably a C 2-4 alkylene group.

[0123] In one embodiment, k is 0.

[0124] In another aspect, k is an integer from 1 to 4.

[0125] In a preferred aspect, k is an integer from 1 to 2.

[0126] In one aspect, k is 1.

[0127] In one aspect, k is 2.

[0128] In one aspect, R a’ is each independently a trivalent group containing an N atom or an O atom.

[0129] In a preferred aspect, R a’ is each independently a trivalent group which may contain an amino bond, an amide bond, a urethane bond, a urea bond, an ether bond, or an ester bond between N, -C(-O)-, and carbon-carbon atoms.

[0130] In one aspect, R a’ is each independently the following group:

Chemical formula

[0131] In one aspect, R a’ is N.

[0132] In one aspect, R a’ is -C(-O)-.

[0133] In the above formula (A2), m3 is an integer from 0 to 4.

[0134] m3 is preferably an integer from 1 to 4, more preferably 1 or 2.

[0135] In one aspect, m3 is 1.

[0136] In one embodiment, m3 is 2.

[0137] In the above formula (A2), R g is, independently of each other, -NR c CO-R e -, -NR c COO-R e -, or -NR c CONR c -R e -. Here, these groups are bonded to R a on the left side.

[0138] The above R g is preferably -NR c CO-R e -.

[0139] The above R c is, independently of each other, a hydrogen atom, a C 1-6 alkyl group, or a C 6-16 aryl group.

[0140] The above C 1-6 alkyl group is preferably a C 1-3 alkyl group, particularly preferably a methyl group. The C 1-6 alkyl group may be linear or branched.

[0141] The above C 6-16 aryl group is preferably a C 6-10 aryl group, more preferably a phenyl group.

[0142] In one embodiment, R c is a hydrogen atom.

[0143] In one embodiment, R c is a methyl group.

[0144] In the above formula, R e is, independently of each other, a single bond or a divalent organic group.

[0145] In one embodiment, Re is a single bond.

[0146] In one embodiment, R e is each independently a divalent organic group.

[0147] The divalent organic group is preferably -R 43 -O x2 -R 44 -(wherein R 43 and R 44 are each independently a single bond or a C 1-20 alkylene group, and x2 is 0 or 1.) It is. Such a C 1-20 The alkylene group may be linear or branched, but is preferably linear. Such a C 1-20 The alkylene group is preferably a C 1-10 alkylene group, more preferably a C 1-6 alkylene group, still more preferably a C 1-3 alkylene group.

[0148] In the above formula (A2), x is an integer of 1 or more.

[0149] In one embodiment, x is preferably an integer of 1 or more and 100 or less, more preferably an integer of 1 or more and 10 or less, still more preferably an integer of 1 or more and 5 or less, for example, an integer of 2 or more and 10 or less, still more preferably an integer of 2 or more and 5 or less.

[0150] In a preferred embodiment, the formula (A2) is the following formula (A2-a):

Chemical formula

[0151] In the above formula (A2-a), R b is each independently R Si R Ac or R c is

[0152] In the above formula (A2-a), at least one R b is R Si is

[0153] In a preferred embodiment, at least one of the R b bonded to the N atom located at each end of the formula (A2-a) is R Si is

[0154] In one embodiment, one of the R b bonded to the N atom located at each end of the formula (A2-a) is R Si and the other is R c is

[0155] In another embodiment, one of the R b bonded to the N atom located at each end of the formula (A2-a) is R Si and the other is R Ac is

[0156] In a preferred embodiment, R Ac is -CONH-X F -OCO-CR 5 =CH2

[0157] The above R j is, independently of each other, -CO-R d -, -O-R d -, or -NR c -R d -. Here, these groups are bonded to R F2 on the left side.

[0158] In one embodiment, R j is, independently of each other, -CO-R d -.

[0159] The above R d is, independently of each other, a single bond or a divalent organic group.

[0160] In one embodiment, R d is a single bond.

[0161] In another embodiment, R d is a divalent organic group.

[0162] R d The divalent organic group in C 1-10 is an alkylene group, preferably a C 2-6 alkylene group, -(CH2) z13 -O-(CH2) z14 -(wherein z13 is an integer from 0 to 6, for example, an integer from 1 to 6, and z14 is an integer from 0 to 6, for example, an integer from 1 to 6). -(CH2) z15 -phenylene-(CH2) z16 -(wherein z15 is an integer from 0 to 6, for example, an integer from 1 to 6, and z16 is an integer from 0 to 6, for example, an integer from 1 to 6), or -(CH2) z17 -NR 10 -(CH2) z18 -(wherein R 10 is a hydrogen atom or a C 1-6 alkyl group, z17 is an integer from 0 to 6, and z18 is an integer from 0 to 6). It is. These groups may be substituted with one or more substituents selected from, for example, a fluorine atom, C 1-6 alkyl group, C 2-6 alkenyl group, and C 2-6 alkynyl group, but are preferably unsubstituted. These groups are bonded to CO on the left side.

[0163] R d The divalent organic group in is preferably -(CH2) z17 -NR 10 -(CH2) z18 -(wherein R 10 is a hydrogen atom or a C 1-6 alkyl group, z17 is an integer from 0 to 6, and z18 is an integer from 0 to 6), more preferably -NR 10 -(CH2) z18 -(wherein R 10 is a hydrogen atom or a C 1-6 alkyl group, and z18 is an integer from 1 to 6).

[0164] The above C 1-10 alkylene group may be linear or branched, but is preferably linear.

[0165] In a preferred embodiment, formula (A2) is formula (A2-b):

Chemical formula

[0166] The fluoropolyether group-containing compounds represented by the above formulas (A1) and (A2) are not particularly limited, but may have a number average molecular weight of 5×10 2 ~2×10 5 . Among such ranges, 2×10 3 ~1×105 , more preferably having a number average molecular weight of 3×10 3 ~2×10 4 is preferred from the viewpoints of refractive index and compatibility. The "number average molecular weight" is 19 the value measured by 19F-NMR.

[0167] The fluoropolyether group-containing compound represented by the above formula (A1) can be obtained by first preparing a fluoropolyether group-containing silane compound having reactive sites such as -NH- and -C(OH)-, and then reacting a compound having a (meth)acrylic group with the above reactive sites.

[0168] In one embodiment, the fluoropolyether group-containing compound represented by the above formula (A1) has the following formula: R 21 OOC-R F2 -COOR 21 (wherein R 21 is a hydrogen atom or a methyl group, and R F2 has the same meaning as described for formula (A1).) and a compound represented by the following formula: R 24 -R 23 -NH-R 22 -SiR 1 n’ R 2 3-n’ (wherein R 22 is a divalent group, R 23 is a divalent group, R 24 is a reactive group such as NH2, R 1 , R 2 , and n' have the same meaning as described for formula (A1).) are reacted to give the following formula: R 2 3-n’ R 1 n’ Si-R 22 -HN-R 23 -R25 -R F2 -R 25 -R 23 -NH-R 22 -SiR 1 n’ R 2 3-n’ to obtain a compound represented by the following. Then, the above compound is reacted with the following formula: R 54 -R 55 -OCOCH=CH2 (wherein R 54 is a reactive group such as -NCO, -COOH, COOCl, etc., R 55 is a divalent group.) or R 56 -OCOCR 57 =CH2 (wherein R 56 is halogen, H, or a monovalent hydrocarbon group, R 57 is a hydrogen atom or C 1-3 alkyl.) can be obtained by reacting with a compound represented by the following.

[0169] In one embodiment, the fluoropolyether group-containing compound represented by the above formula (A1) is the following formula: FOC-R F2 -COF (wherein R F2 has the same meaning as described for formula (A1).) A compound represented by the following is reacted with Br-Mg-CH2CH=CH2 to obtain a compound represented by (CH2=CHCH2)2(HO)C-R F2 -C(OH)(CH2CH=CH2)2 Then, the above compound is reacted with the following formula: HSiR 1 n’ R 2 3-n’ to obtain (R 2 3-n’R 1 n’ Si-CH2CH2CH2)2(HO)C-R F2 -C(OH)(CH2CH2CH2-SiR 1 n’ R 2 3-n’ )2 to obtain a compound represented by the following. Then, the above compound is reacted with the following formula: R 34 -R 35 -OCOCH=CH2 (wherein R 34 is a reactive group such as -NCO, -COOH, etc., R 35 is a divalent group.) to obtain a compound represented by the following.

[0170] In one embodiment, the fluoropolyether group-containing compound represented by the above formula (A1) is a compound represented by the following formula: HOCH2-R F2 -CH2OH (wherein R F2 has the same meaning as described for formula (A1).) is reacted with

Chemical formula

Chemical formula

Chemical formula

[0171] In one aspect, the fluoropolyether group-containing compound represented by the above formula (A1) is the following formula:

Chemical formula

Chemical formula

Chemical formula

[0172] In one aspect, the fluoropolyether group-containing compound represented by the above formula (A2) is the following formula: R 21 OOC-R F2 -COOR 21 [wherein R 21 is a hydrogen atom or a methyl group, and R F2 has the same meaning as described for formula (A2).] a compound represented by and the following formula: NH2-R 9 -(NH-R 9 ) k -NH2 [wherein R 9 , and k have the same meaning as described for formula (A2).] are reacted to obtain R21 OOC-(R F2 -CONH-R 9 -(NH-R 9 ) k -NHCO) x -R F2 -COOR 21 [wherein, R 21 is a hydrogen atom or a methyl group, and R F2 , R 9 , and k are as defined in the description regarding formula (A2).] is obtained. Then, the obtained compound is reacted with NR 23 m H 2-m -R 22 -SiR 1 n’ R 2 3-n’ [wherein, R 23 is an alkyl group or a phenyl group of C 1-6 , m is 0 or 1, R 22 is a divalent group, and R 1 , R 2 , and n' are as defined in the description regarding formula (A2).] and the compound represented by the following formula: R 2 3-n’ R 1 n’ Si-R 22 -HNOC-(R F2 -CONH-R 9 -(NH-R 9 ) k -NHCO) x -R F2 -CONH-R 22 -SiR 1 n’ R 2 3-n’ to obtain a compound represented by the following formula: R 34 -R 35 -OCOCH=CH2 [wherein, R 34 is a reactive group such as -NCO, -COOH, etc., R 35 is a divalent group.] By reacting with the compound represented by the formula, a compound represented by the formula (A2) can be obtained.

[0173] In one embodiment, the fluoropolyether group-containing compound represented by the above formula (A2) has the following formula: R 21 OOC-R F2 -COOR 21 [Wherein, R 21 is a hydrogen atom or a methyl group, and R F2 has the same meaning as described for formula (A2).] The compound represented by the formula and the following formula: NH2-R 9 -(CH(OH)-R 9 ) k -NH2 [Wherein, R 9 , and k have the same meaning as described for formula (A2).] React with to obtain R 21 OOC-(R F2 -CONH-R 9 -(CH(OH)-R 9 ) k -NHCO) x -R F2 -COOR 21 [Wherein, R 21 is a hydrogen atom or a methyl group, and R F2 , R 9 , and k have the same meaning as described for formula (A2).] Next, the obtained compound and NR 23 m H 2-m -R 22 -SiR 1 n’ R 2 3-n’ [Wherein, R 23 is an alkyl group or a phenyl group of C 1-6 , m is 0 or 1, and R 22is a divalent group, and R 1 , R 2 , and n’ have the same meanings as described for formula (A2).] is reacted with a compound represented by the following formula: R 2 3-n’ R 1 n’ Si-R 22 -HNOC-(R F2 -CONH-R 9 -(CH(OH)-R 9 ) k -NHCO) x -R F2 -CONH-R 22 -SiR 1 n’ R 2 3-n’ to obtain a compound represented by the following formula: R 34 -R 35 -OCOCH=CH2 [wherein, R 34 is a reactive group such as -NCO, -COOH, etc., R 35 is a divalent group.] By reacting with a compound represented by the following formula:

[0174] In one embodiment, the fluoropolyether group-containing compound represented by the above formula (A2) is a compound represented by the following formula: R 21 OOC-R F2 -COOR 21 [wherein, R 21 is a hydrogen atom or a methyl group, and R F2 has the same meaning as described for formula (A2).] is reacted with a compound represented by the following formula: NH2-R 9 -(NH-R 9 ) k -NH2 [wherein, R 9 , and k have the same meanings as described for formula (A2).] react with R 21 OOC-(R F2 -CONH-R 9 -(NH-R 9 ) k -NHCO) x -R F2 -COOR 21 [wherein, R 21 is a hydrogen atom or a methyl group, and R F2 , R 9 , and k have the same meanings as described for formula (A2).] to obtain. Then, react the obtained compound with NH2-R 9‘ -NH2 [wherein, R 9‘ has the same meaning as described for R 9 .] and the compound represented by the following formula R 21 OOC-(R F2 -CONH-R 9 -(NH-R 9 ) k -NHCO) x -(R F2 -CONH-R 9 ‘-NHCO) x’ -R F2 -COOR 21 [wherein, R 21 is a hydrogen atom or a methyl group, R F2 , R 9 , and k have the same meanings as described for formula (A2), and R 9‘ has the same meaning as described for R 9 .] to obtain. Then, react the obtained compound with NR 23 m H 2-m -R 22 -SiR 1 n’ R 2 3-n’ [wherein, R 23 is C 1-6is an alkyl group or a phenyl group, m is 0 or 1, and R 22 is a divalent group, and R 1 , R 2 , and n’ are as defined in relation to formula (A2).] is reacted with a compound represented by the following formula: R 2 3-n’ R 1 n’ Si-R 22 -HNOC-(R F2 -CONH-R 9 -(NH-R 9 ) k -NHCO) x -(R F2 -CONH-R 9 ‘-NHCO) x’ -R F2 -CONH-R 22 -SiR 1 n’ R 2 3-n’ to obtain a compound represented by the following formula: R 34 -R 35 -OCOCH=CH2 [wherein, R 34 is a reactive group such as -NCO, -COOH, etc., R 35 is a divalent group.] By reacting with a compound represented by the following formula:

[0175] Those skilled in the art can appropriately set the reaction conditions for each step of the above reaction.

[0176] Component (B): (Meth)acrylic monomer

[0177] The curable composition of the present disclosure contains a curable monomer, typically a (meth)acrylic monomer. It should be noted that component (B) is other than the compounds represented by formula (A1) and formula (A2).

[0178] In one aspect, examples of the above (meth)acrylic monomer include, for example, (a) urethane (meth)acrylate, (b) epoxy (meth)acrylate, (c) polyester (meth)acrylate, (d) polyether (meth)acrylate, (e) silicone (meth)acrylate, (f) (meth)acrylate monomer, and the like.

[0179] Specific examples of the above (meth)acrylic monomer include the following. (a) Examples of urethane (meth)acrylate include poly[(meth)acryloyloxyalkyl] isocyanurates typified by tris(2-hydroxyethyl) isocyanurate diacrylate and tris(2-hydroxyethyl) isocyanurate triacrylate. (b) Epoxy (meth)acrylate is obtained by adding a (meth)acryloyl group to an epoxy group, and those using bisphenol A, bisphenol F, phenol novolak, or an alicyclic compound as starting materials are common. (c) Examples of the polyhydric alcohol constituting the polyester part of polyester (meth)acrylate include ethylene glycol, 1,4-butanediol, 1,6-hexanediol, diethylene glycol, trimethylolpropane, dipropylene glycol, polyethylene glycol, polypropylene glycol, pentaerythritol, dipentaerythritol, and the like. Examples of the polybasic acid include phthalic acid, adipic acid, maleic acid, trimellitic acid, itaconic acid, succinic acid, terephthalic acid, alkenyl succinic acid, and the like. (d) Examples of polyether (meth)acrylate include polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, polyethylene glycol-polypropylene glycol di(meth)acrylate, and the like. (e) Silicone (meth)acrylate is obtained by modifying one end or both ends of dimethylpolysiloxane having a molecular weight of 1,000 to 10,000 with a (meth)acryloyl group, and examples thereof include the following compounds.

[0180] [Chemical]

[0181] (f) Examples of the (meth)acrylate monomer include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, sec-butyl (meth)acrylate, t-butyl (meth)acrylate, n-pentyl (meth)acrylate, 3-methylbutyl (meth)acrylate, n-hexyl (meth)acrylate, 2-ethyl-n-hexyl (meth)acrylate, n-octyl (meth)acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, benzyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 5-hydroxypentyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 4-hydroxycyclohexyl (meth)acrylate, neopentyl glycol mono(meth)acrylate, 3-chloro-2-hydroxypropyl (meth)acrylate, (1,1-dimethyl-3-oxobutyl)(meth)acrylate, 2-acetoxyethyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, neopentyl glycol mono(meth)acrylate, 3-chloro-2-hydroxypropyl (meth)acrylate, glycerin mono(meth)acrylate, ethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, 2-isocyanateethyl (meth)acrylate, 1,1-(bis(meth)acryloyloxymethyl)ethyl isocyanate, glycidyl (meth)acrylate, (meth)acrylic acid, etc.

[0182] In one aspect, examples of the (meth)acrylic monomer include fluorine-containing (meth)acrylic monomers.

[0183] In one aspect, the fluorine-containing (meth)acrylic monomer has the following formula (M): (CH2=CR 71 -COO-) m1 -X 7 -R F72 -X 7 -(OCO-CR 71 =CH2) m1 [In the formula: R F72 is -Rf 2 p -R F -O q - and Rf 2 is an alkylene group which may be substituted by one or more fluorine atoms, 1-6 R F are each independently a divalent fluoropolyether group, p is 0 or 1, q is each independently 0 or 1, R 71 are each independently a hydrogen atom or a C 1-6 alkyl group, X 7 are each independently a 2- to 5-valent organic group, m1 is each independently an integer from 1 to 4.] It may be a compound represented by the formula.

[0184] The above Rf 2 R F p, and q have the same meanings as those in the above formulas (A1) and (A2).

[0185] In one aspect, R 71 is a hydrogen atom.

[0186] In another aspect, R 71 are each independently C1-6 It is an alkyl group.

[0187] The above C 1-6 The alkyl group is preferably a C 1-3 alkyl group, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. The C 1-6 alkyl group may be linear or branched.

[0188] X 7 is each independently a divalent to pentavalent organic group.

[0189] In one embodiment, X 7 is a divalent organic group.

[0190] In another embodiment, X 7 is a trivalent to pentavalent organic group.

[0191] In a preferred embodiment, X 7 is each independently a single bond or the following formula: -(R 55 ) p7 -(R 56 ) q7 - [Wherein: R 55 is a single bond, a C 1-20 alkylene group, or an o-, m- or p-phenylene group, R 56 is each independently a group selected from the group consisting of -O-, -S-, o-, m- or p-phenylene group, -COO-, -OCO-, -CONR 57 -, -NR 57 CO-, -O-CONR 57 -, -NR 57 CO-O-, and -NR 57 -. R 57 is each independently a hydrogen atom, a phenyl group, or a C 1-6 alkyl group, p7 is an integer from 0 to 6, q7 is an integer from 0 to 6, Here, at least one of p7 and q7 is 1 or more, and the order of existence of each repeating unit enclosed in parentheses with p7 or q7 attached is arbitrary. It may be a divalent organic group represented by. In addition, X 7 In, two or more of the same kind of R 56 do not bond continuously.

[0192] In one aspect, X 7 is a single bond.

[0193] In another aspect, X 7 is a group represented by -(R 55 ) p7 -(R 56 ) q7 -.

[0194] R 55 is preferably a C 1-20 alkylene group, or an o-, m-, or p-phenylene group, more preferably a C 1-20 alkylene group. The above C 1-20 alkylene group may preferably be a C 1-10 alkylene group, more preferably a C 1-6 alkylene group. Such an alkylene group may be linear or branched.

[0195] R 56 is preferably -O-, -COO-, -OCO-, -CONR 57 -, -NR 57 CO-, -O-CONR 57 -, -NR 57 CO-O-, or -NR 57 -, more preferably -COO-, -OCO-, -CONR 57 -, -NR 57 CO-, -O-CONR 57 -, or -NR 57 CO-O-, even more preferably -CONR 57 -.

[0196] R 57 is preferably a hydrogen atom, or a C 1-6It is an alkyl group.

[0197] In one embodiment, R 57 is a hydrogen atom.

[0198] In another embodiment, R 57 is a C 1-6 alkyl group, preferably a C 1-3 alkyl group, more preferably a methyl group. The above alkyl group may be linear or branched.

[0199] In one embodiment, p7 is 0.

[0200] In another embodiment, p7 is an integer from 1 to 6, for example, an integer from 1 to 3, or 1.

[0201] In one embodiment, q7 is 0.

[0202] In another embodiment, q7 is an integer from 1 to 6, for example, an integer from 1 to 3, or 1.

[0203] In a preferred embodiment, the fluorine-containing (meth)acrylic monomer can be 1,6-bis(acryloyloxy)-2,2,3,3,4,4,5,5-octafluorohexane.

[0204] In one aspect, the fluorine-containing (meth)acrylic monomer may be, for example, 2,2,2-trifluoroethyl (meth)acrylate, 1,1,1,3,3,3-hexafluoroisopropyl (meth)acrylate, 2,2,3,3,4,4,4-heptafluorobutyl (meth)acrylate, 2,2,3,4,4,4-hexafluorobutyl (meth)acrylate, 1H,1H,2H,2H-nonafluorohexyl (meth)acrylate, 1H,1H,5H-octafluoropentyl (meth)acrylate, pentafluorophenyl (meth)acrylate, 2,2,3,3,3-pentafluoropropyl (meth)acrylate, 2,2,3,3-tetrafluoropropyl (meth)acrylate, 1H,1H,2H,2H-tridecafluoro-n-octyl (meth)acrylate, 1H,1H,2H,2H-heptadecafluorodecyl (meth)acrylate, 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctyl (meth)acrylate, 1,6-bis(acryloyloxy)-2,2,3,3,4,4,5,5-octafluorohexane, methyl 2-fluoroacrylate, and the like.

[0205] In a preferred aspect, the fluorine-containing (meth)acrylic monomer can be 2,2,3,3,4,4,4-heptafluorobutyl (meth)acrylate.

[0206] Component (C): Radical polymerization initiator

[0207] The radical polymerization initiator may preferably be a radical photopolymerization initiator. Examples of the radical photopolymerization initiator include α-diketones such as benzyl and diacetyl; acyloins such as benzoin; acyloin ethers such as benzoin methyl ether, benzoin ethyl ether, and benzoin isopropyl ether; thioxanthones such as thioxanthone, 2,4-diethylthioxanthone, and thioxanthone-4-sulfonic acid; benzophenones such as benzophenone, 4,4'-bis(dimethylamino)benzophenone, and 4,4'-bis(diethylamino)benzophenone; acetophenones such as acetophenone, 2-(4-toluenesulfonyloxy)-2-phenylacetophenone, p-dimethylaminoacetophenone, 2,2'-dimethoxy-2-phenylacetophenone, p-methoxyacetophenone, 2-methyl[4-(methylthio)phenyl]-2-morpholino-1-propanone, and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one; quinones such as anthraquinone and 1,4-naphthoquinone; aminobenzoic acids such as ethyl 2-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, (n-butoxy)ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, and 2-ethylhexyl 4-dimethylaminobenzoate; halogen compounds such as phenacyl chloride and trihalomethylphenyl sulfone; acylphosphine oxides; peroxides such as di-t-butyl peroxide, etc.

[0208] In a preferred embodiment, the radical polymerization initiator is benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, thioxanthone, 2,4-diethylthioxanthone, thioxanthone-4-sulfonic acid, benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, acetophenone, 2-(4-toluenesulfonyloxy)-2-phenylacetophenone, p-dimethylaminoacetophenone, 2,2'-dimethoxy-2-phenylacetophenone, p-methoxyacetophenone, 2-methyl[4-(methylthio)phenyl]-2-morpholino-1-propanone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, anthraquinone, 1,4-naphthoquinone, ethyl 2-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, (n-butoxy)ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, phenacyl chloride, trihalomethylphenyl sulfone, acylphosphine oxide, or di-t-butyl peroxide, methyl benzoylformate, 1-hydroxy-cyclohexyl-phenyl-ketone, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]phenyl}-2-methyl-propan-1-one, 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-1-butanone, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, bis(η5-2,4-cyclopentadien-1-yl)-bis(2,6-difluoro-3-(1H-pyrrol-1-yl)-phenyl)titanium, 1,2-octanedione, 1-[4-(phenylthio)-,2-(O-benzoyloxime)], ethanone,1-[9-Ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-,1-(O-acetyloxime), 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide, t-butyl hydroperoxide, cumene hydroperoxide, diisopropylbenzene hydroperoxide, permentahydroperoxide, or t-methylbutyl hydroperoxide.,

[0209] Examples of commercially available products of the above radical photoinitiators are as follows. OMNIRAD 651: 2,2-dimethoxy-1,2-diphenylethane-1-one, OMNIRAD 184: 1-hydroxy-cyclohexyl-phenyl-ketone, OMNIRAD 2959: 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one, OMNIRAD 127: 2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]phenyl}-2-methyl-propan-1-one, OMNIRAD 907: 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one, OMNIRAD 369: 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1, OMNIRAD 379: 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone, OMNIRAD 819: bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, OMNIRAD 784: bis(η5-2,4-cyclopentadien-1-yl)-bis(2,6-difluoro-3-(1H-pyrrol-1-yl)-phenyl)titanium, OMNIRAD OXE 01: 1,2-octanedione,1-[4-(phenylthio)-,2-(O-benzoyloxime)], OMNIRAD OXE 02: Ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyl oxime), OMNIRAD 261, OMNIRAD 369, OMNIRAD 500, DAROCUR 1173: 2-Hydroxy-2-methyl-1-phenyl-propan-1-one, DAROCUR TPO: 2,4,6-Trimethylbenzoyl-diphenyl-phosphine oxide, DAROCUR 1116, DAROCUR 2959, DAROCUR 1664, DAROCUR 4043, OMNIRAD 754 Oxyphenylacetic acid: A mixture of 2-[2-oxo-2-phenylacetoxyethoxy]ethyl ester and oxyphenylacetic acid, 2-(2-hydroxyethoxy)ethyl ester, OMNIRAD 500: A mixture of OMNIRAD 184 and benzophenone (1 :1), OMNIRAD 1300: A mixture of OMNIRAD 369 and OMNIRAD 651 (3:7), OMNIRAD 1800: A mixture of CGI403 and OMNIRAD 184 (1:3), OMNIRAD 1870: A mixture of CGI403 and OMNIRAD 184 (7:3), DAROCUR 4265: A mixture of DAROCUR TPO and DAROCUR 1173 (1:1). Note that OMNIRAD is manufactured by BASF, and DAROCUR is manufactured by Merck Japan.

[0210] The content of component (A) is preferably 60% by mass or more, more preferably 70% by mass or more, still more preferably 80% by mass or more, for example 85% by mass or more, 90% by mass or more, or 95% by mass or more, based on the total amount of component (A) and component (B).

[0211] The content of component (A) is preferably 99% by mass or less, more preferably 95% by mass or less, for example 90% by mass or less, 85% by mass or less, or 80% by mass or less, based on the total amount of component (A) and component (B).

[0212] The content of component (A) can be, for example, 60 to 99% by mass, preferably 60 to 95% by mass, more preferably 60 to 90% by mass, still more preferably 60 to 80% by mass, for example 70 to 90% by mass, or 80 to 90% by mass, based on the total amount of component (A) and component (B).

[0213] By containing component (A) and component (B), particularly in the above ratios, the curable composition of the present disclosure provides a cured product exhibiting excellent adhesion, particularly excellent adhesion to glass, quartz, etc. Further, since the obtained cured product has a relatively low refractive index, particularly lower than that of glass or quartz, it can be useful as a cladding material in an optical waveguide.

[0214] Component (C) is preferably contained in an amount of 0.1 to 20 parts by mass, more preferably 1 to 10 parts by mass, still more preferably 1 to 5 parts by mass, based on 100 parts by mass in total of the above components (A) and (B).

[0215] The curable composition of the present disclosure may contain a solvent.

[0216] The above solvent is preferably an aliphatic hydrocarbon, an aromatic hydrocarbon, an ester, a ketone, a glycol ether, an alcohol, a glycol, a cyclic ether, an amide, an ether alcohol, a perfluoroaliphatic hydrocarbon having 5 to 12 carbon atoms, a polyfluoroaromatic hydrocarbon, a polyfluoroaliphatic hydrocarbon, a hydrofluorocarbon, a hydrochlorofluorocarbon, or a hydrofluoroether. The solvent may be a mixed solvent of two or more of these.

[0217] In a preferred embodiment, the solvent is an alcohol, a hydrofluoroether, or a mixed solvent of two or more of these.

[0218] Examples of the aliphatic hydrocarbons include hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, mineral spirit, etc.

[0219] Examples of the aromatic hydrocarbons include benzene, toluene, xylene, naphthalene, solvent naphtha, etc.

[0220] Examples of the esters include methyl acetate, ethyl acetate, propyl acetate, n-butyl acetate, isopropyl acetate, isobutyl acetate, cellosolve acetate, propylene glycol methyl ether acetate, carbitol acetate, diethyl oxalate, ethyl pyruvate, ethyl-2-hydroxybutyrate, ethyl acetoacetate, amyl acetate, methyl lactate, ethyl lactate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 2-hydroxyisobutyrate, ethyl 2-hydroxyisobutyrate, etc.

[0221] Examples of the ketones include acetone, methyl ethyl ketone, methyl isobutyl ketone, 2-hexanone, cyclohexanone, methylaminoketone, 2-heptanone, etc.

[0222] Examples of the glycol ethers include ethyl cellosolve, methyl cellosolve, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, dipropylene glycol dimethyl ether, diethylene glycol monoethyl ether acetate, etc.

[0223] Examples of the alcohols include methanol, ethanol, iso-propanol, n-butanol, isobutanol, tert-butanol, sec-butanol, 3-pentanol, octyl alcohol, 3-methyl-3-methoxybutanol, tert-amyl alcohol, etc. The alcohols are preferably methanol, ethanol, and iso-propanol.

[0224] Examples of the glycols include ethylene glycol, propylene glycol, etc.

[0225] Examples of the cyclic ethers include tetrahydrofuran, tetrahydropyran, dioxane, etc.

[0226] Examples of the amides include N,N-dimethylformamide, N,N-dimethylacetamide, etc.

[0227] Examples of the ether alcohols include methyl cellosolve, cellosolve, isopropyl cellosolve, butyl cellosolve, diethylene glycol monomethyl ether, etc.

[0228] Examples of the C5-C12 perfluoroaliphatic hydrocarbons include perfluorohexane, perfluoromethylcyclohexane, perfluoro-1,3-dimethylcyclohexane, etc.

[0229] Examples of the polyfluoroaromatic hydrocarbons include bis(trifluoromethyl)benzene, etc.

[0230] Examples of the polyfluoroaliphatic hydrocarbons include C6F 13 CH2CH3 (for example, Asahiklin (registered trademark) AC-6000 manufactured by Asahi Glass Co., Ltd.), 1,1,2,2,3,3,4-heptafluorocyclopentane (for example, Zeorola (registered trademark) H manufactured by Nippon Zeon Co., Ltd.), etc.

[0231] Examples of the hydrofluorocarbon (HFC) include 1,1,1,3,3-pentafluorobutane (HFC-365mfc).

[0232] Examples of the hydrochlorofluorocarbon (HCFC) include 1,1,2-trichloro-1,2,2-trifluoroethane, 1,2-dichloro-1,1,2,2-tetrafluoroethane, 1,1-dichloro-1,2,2,3,3-pentafluoropropane (HCFC225) (e.g., Asahiklin (registered trademark) AK225).

[0233] Examples of the hydrofluoroether (HFE) include alkyl perfluoroalkyl ethers such as perfluoropropyl methyl ether (C3F7OCH3) (e.g., Novec (trademark) 7000 manufactured by Sumitomo 3M Limited), perfluorobutyl methyl ether (C4F9OCH3) (e.g., Novec (trademark) 7100 manufactured by Sumitomo 3M Limited), perfluorobutyl ethyl ether (C4F9OC2H5) (e.g., Novec (trademark) 7200 manufactured by Sumitomo 3M Limited), perfluorohexyl methyl ether (C2F5CF(OCH3)C3F7) (e.g., Novec (trademark) 7300 manufactured by Sumitomo 3M Limited) (the perfluoroalkyl group and the alkyl group may be linear or branched), CF3CH2OCF2CHF2 (e.g., Asahiklin (registered trademark) AE-3000 manufactured by Asahi Glass Co., Ltd.).

[0234] In a preferred embodiment, the solvent is methanol, ethanol, iso-propanol, perfluoropropyl methyl ether, perfluorobutyl methyl ether, perfluorobutyl ethyl ether, perfluorohexyl methyl ether, or CF3CH2OCF2CHF2, or a mixed solvent of two or more thereof.

[0235] The content of the above solvent may be preferably 20 to 90% by mass, more preferably 40 to 90% by mass, based on the total amount of components (A) to (C).

[0236] The curable composition of the present disclosure may contain a (non-reactive) fluoropolyether compound that can be understood as a fluorinated oil, preferably a perfluoro(poly)ether compound (hereinafter collectively referred to as "fluorinated oil"), a (non-reactive) silicone compound that can be understood as a silicone oil (hereinafter referred to as "silicone oil"), a catalyst, alcohols, surfactants, polymerization inhibitors, sensitizers, UV fluorescent agents, etc.

[0237] The fluorinated oil is not particularly limited, and examples thereof include compounds (perfluoro(poly)ether compounds) represented by the following general formula (3). Rf 5 -(OC4F8) a’ -(OC3F6) b’ -(OC2F4) c’ -(OCF2) d’ -Rf 6 ···(3) In the formula, Rf 5 represents an alkyl group having 1 to 16 carbon atoms which may be substituted by one or more fluorine atoms (preferably a perfluoroalkyl group of C 1-16 ), Rf 6 represents an alkyl group having 1 to 16 carbon atoms which may be substituted by one or more fluorine atoms (preferably a perfluoroalkyl group of C 1-16 ), a fluorine atom or a hydrogen atom, and Rf 5 and Rf 6 are more preferably each independently a perfluoroalkyl group of C 1-3 . a', b', c' and d' each represent four types of repeating unit numbers of perfluoro(poly)ether that constitute the main backbone of the polymer, and are each independently an integer of 0 or more and 300 or less, and the sum of a', b', c' and d' is at least 1, preferably 1 to 300, more preferably 20 to 300. The order of existence of each repeating unit enclosed in parentheses with subscripts a', b', c' or d' is arbitrary in the formula. These repeating units may be linear, branched, or may contain a ring structure. For example, -(OC4F8)- may be any of -(OCF2CF2CF2CF2)-, -(OCF(CF3)CF2CF2)-, -(OCF2CF(CF3)CF2)-, -(OCF2CF2CF(CF3))-, -(OC(CF3)2CF2)-, -(OCF2C(CF3)2)-, -(OCF(CF3)CF(CF3))-, -(OCF(C2F5)CF2)- and (OCF2CF(C2F5))-, but is preferably -(OCF2CF2CF2CF2)-. -(OC3F6)- may be any of -(OCF2CF2CF2)-, -(OCF(CF3)CF2)- and (OCF2CF(CF3))-, and is preferably -(OCF2CF2CF2)-. -(OC2F4)- may be any of -(OCF2CF2)- and (OCF(CF3))-, but is preferably -(OCF2CF2)-.

[0238] The above ring structure is the following three-membered ring or four-membered ring:

Chemical formula

[0239] For example, (OC4F8) is

Chemical formula

[0240] Examples of the perfluoro(poly)ether compound represented by the above general formula (3) include compounds represented by any of the following general formulas (3a) and (3b) (which may be a mixture of one or more kinds). Rf 5 -(OCF2CF2CF2) b” -Rf 6 ···(3a) Rf 5 -(OCF2CF2CF2CF2) a” -(OCF2CF2CF2) b” -(OCF2CF2) c” -(OCF2) d” -Rf 6 ···(3b) In these formulas, Rf 5 and Rf 6 are as defined above; in formula (3a), b” is an integer of 1 or more and 100 or less; in formula (3b), a” and b” are each independently an integer of 0 or more and 30 or less, and c” and d” are each independently an integer of 1 or more and 300 or less. The order of existence of each repeating unit enclosed in parentheses with subscripts a”, b”, c”, d” is arbitrary in the formula.

[0241] From another perspective, the fluorinated oil may be a compound represented by the general formula Rf 3 -F (wherein Rf 3 is a perfluoroalkyl group). It may also be a chlorotrifluoroethylene oligomer. 5-16 is a perfluoroalkyl group). It may also be a chlorotrifluoroethylene oligomer.

[0242] The above fluorinated oil may have an average molecular weight of 500 to 10,000. The molecular weight of the fluorinated oil can be measured using GPC.

[0243] The fluorine-containing oil may be contained in the curable composition of the present disclosure, for example, in an amount of 0 to 50% by mass, preferably 0 to 30% by mass, more preferably 0 to 5% by mass. In one aspect, the curable composition of the present disclosure is substantially free of the fluorine-containing oil. Substantially free of the fluorine-containing oil means that it may contain no fluorine-containing oil at all or may contain a trace amount of the fluorine-containing oil.

[0244] As the silicone oil, for example, a linear or cyclic silicone oil having a siloxane bond of 2,000 or less can be used. The linear silicone oil may be a so-called straight silicone oil and a modified silicone oil. Examples of the straight silicone oil include dimethyl silicone oil, methylphenyl silicone oil, and methylhydrogen silicone oil. Examples of the modified silicone oil include those obtained by modifying the straight silicone oil with alkyl, aralkyl, polyether, higher fatty acid ester, fluoroalkyl, amino, epoxy, carboxyl, alcohol, etc. Examples of the cyclic silicone oil include cyclic dimethylsiloxane oil.

[0245] In the curable composition of the present disclosure, such a silicone oil may be contained in an amount of, for example, 0 to 300 parts by mass, preferably 50 to 200 parts by mass, based on 100 parts by mass in total of the fluoropolyether group-containing compound and the fluoropolyether group-containing silane compound of the present disclosure (in the case of two or more kinds, the total thereof, the same applies hereinafter).

[0246] The catalyst is not particularly limited, and examples thereof include acids (e.g., acetic acid, trifluoroacetic acid, etc.), bases (e.g., ammonia, triethylamine, diethylamine, etc.), transition metals (e.g., Ti, Ni, Sn, etc.), metal complexes, such as tin-based catalysts, titanium-based catalysts, zirconia-based catalysts, bismuth-based catalysts, organic amine-based catalysts, etc.

[0247] Examples of the tin-based catalyst include di-n-butyltin(IV) dilaurate. Examples of the above titanium-based catalysts include titanium diisopropoxybis(ethylacetoacetate), titanium tetra-n-butoxide, titanium tetra-2-ethylhexoxide, and titanium tetraacetylacetonate. Examples of the above zirconia-based catalysts include zirconium tetraacetylacetonate, zirconium tetra-n-butoxide, and zirconium dibutoxybis(ethylacetoacetate). Examples of the above bismuth-based catalysts include bismuth tris(2-ethylhexanoate). Examples of the above organic amine-based catalysts include diazabicycloundecene.

[0248] The above catalysts may be added to the curable composition immediately before use.

[0249] The above catalysts may be additionally added to the curable composition immediately before use according to the method of use.

[0250] The above catalysts may preferably be contained in an amount of 0.1 to 20 parts by mass, more preferably 0.2 to 10 parts by mass, and even more preferably 0.5 to 5 parts by mass, based on 100 parts by mass in total of the above components (A) and (B).

[0251] Examples of the above alcohols include alcohols having 1 to 6 carbon atoms which may be substituted by one or more fluorine atoms, such as methanol, ethanol, iso-propanol, tert-butanol, CF3CH2OH, CF3CF2CH2OH, and (CF3)2CHOH. By adding these alcohols to the curable composition, the stability of the curable composition is improved, and the compatibility between the perfluoropolyether group-containing compound and the fluoropolyether group-containing silane compound and the solvent is also improved.

[0252] The above alcohol is preferably methanol, ethanol, 2,2,3,3,3-pentafluoro-1-propanol, or 2,2,2-trifluoroethanol.

[0253] In addition to the above-described components, the curable composition of the present disclosure may contain trace amounts of impurities such as Pt, Rh, Ru, 1,3-divinyltetramethyldisiloxane, triphenylphosphine, NaCl, KCl, and condensates of silanes.

[0254] The viscosity of the curable composition of the present disclosure can preferably be 5000 mPa·s or less, more preferably 3000 mPa·s or less, and even more preferably 2000 mPa·s or less. By reducing the viscosity of the curable composition, it becomes possible to apply the curable composition to finer-shaped locations. Also, the viscosity of the curable composition of the present disclosure can preferably be 100 mPa·s or more, more preferably 500 mPa·s or more, and even more preferably 1000 mPa·s or more. By increasing the viscosity of the curable composition, it becomes easier to form a film with a large thickness and control wet spreading.

[0255] In one aspect, the viscosity of the curable composition of the present disclosure can preferably be 100 to 5000 mPa·s, more preferably 500 to 3000 mPa·s, and even more preferably 1000 to 2000 mPa·s.

[0256] (Use) The cured product of the curable composition of the present disclosure can be used, for example, as a cladding material, particularly a cladding material for an optical waveguide. Since the cured product of the curable composition of the present disclosure has a low refractive index and high adhesion after curing, it is particularly suitable for the above uses.

[0257] The cured product of the curable composition of the present disclosure can also be used as a potting material, a sealing material, etc. The cured product of the curable composition of the present disclosure can be used, for example, by filling and curing the voids of electronic components (for example, the bonded portion between a housing and a printed circuit board, or the gap between a resin-molded metal terminal portion and a molding resin).

[0258] Since the cured product of the curable composition of the present disclosure can form a layer having good adhesion and alcohol resistance to various substrates, it can be used as a hard coat agent.

[0259] Since the curable composition of the present disclosure can form a cured product having good adhesiveness to a metal or plastic substrate, it can be particularly useful as an adhesive or a sealing material for applications around electric and electronic components and in-vehicle components. Since the curable composition of the present disclosure has a good elastic modulus particularly at low temperatures, it can be usefully used in automotive members (for example, sealing materials, specifically, gaskets), etc., particularly automotive members that can be used in cold regions (for example, -50°C or lower). Furthermore, the cured product of the curable composition of the present disclosure can also be useful as a resin mold (replica mold) for nanoimprinting.

[0260] The cured product of the curable composition of the present disclosure has good chemical resistance, acid resistance, and base resistance. Such a cured product of the curable composition of the present disclosure can also be used in chemical plants, semiconductor manufacturing apparatuses, etc.

[0261] The present disclosure provides a cured product obtained from the curable composition of the present disclosure. Since the curable composition of the present disclosure is excellent in curability and coatability, it can be a cured product used in various applications.

[0262] The present disclosure includes an article including a substrate and a cured product layer in which the curable composition of the present disclosure is cured on the substrate.

[0263] Substrates that can be used in the present disclosure can be composed of, for example, glass, resin (natural or synthetic resin, for example, it may be a general plastic material), OCA (Optical Clear Adhesive), polarizing plate metal, ceramics, semiconductors (silicon, germanium, etc.), electronic devices, fibers (woven fabrics, non-woven fabrics, etc.), furs, leathers, woods, ceramics, stones, etc., building members, etc., sanitary products, any suitable material.

[0264] In a preferred embodiment, the substrate can be glass, resin, polarizing plate, OCA (Optical Clear Adhesive), or metal.

[0265] As the glass, sapphire glass, soda-lime glass, alkali aluminosilicate glass, borosilicate glass, non-alkali glass, crystal glass, and fused silica glass are preferable, and chemically strengthened soda-lime glass, chemically strengthened alkali aluminosilicate glass, and chemically bonded borosilicate glass are particularly preferable.

[0266] The shape of the base material is not particularly limited, and may be, for example, a plate shape, a film, or other forms. Further, the surface area of the base material on which the cured product layer is to be formed may be at least a part of the base material surface, and can be appropriately determined according to the use and specific specifications of the article to be manufactured.

[0267] The article of the present disclosure can be manufactured by forming a layer of the curable composition of the present disclosure on the surface of the base material, post-treating this layer as necessary, and thereby forming a layer from the curable composition of the present disclosure.

[0268] The formation of the layer of the curable composition of the present disclosure can be carried out by applying the curable composition to the surface of the base material so as to cover the surface. The coating method is not particularly limited. For example, wet coating methods and dry coating methods can be used.

[0269] Examples of wet coating methods include dip coating, bar coating, spin coating, flow coating, spray coating, roll coating, gravure coating, needle dispense, jet dispense, and similar methods. The wet coating method is preferably bar coating, spin coating, flow coating, roll coating, needle dispense, or jet dispense.

[0270] In a preferred embodiment, the article of the present disclosure can be an electric and electronic component, an in-vehicle component, an automotive member (for example, a sealing material, specifically, a gasket), a chemical plant, a semiconductor manufacturing apparatus, or the like.

[0271] Further, the article of the present disclosure may be a medical device or a medical material.

[0272] The thickness of the above layer is not particularly limited, and may be, for example, 1 μm or more, 10 μm or more, or 100 μm or more. Further, the thickness of the above layer is not particularly limited, and may be 1000 μm or less, 500 μm or less, or 100 μm or less.

[0273] As described above in detail, the curable composition, cured product, and article of the present disclosure have been described. Note that these of the present disclosure are not limited to those exemplified above.

Examples

[0274] Hereinafter, the compounds of the present disclosure will be described in Examples, but the present disclosure is not limited to the following Examples. In the present Examples, the order of the repeating units constituting the fluoropolyether is arbitrary, and the chemical formulas shown below indicate the average composition.

[0275] Component (A): Fluoropolyether group-containing compound Compound (A-1): (CH3O)3SiCH2CH2CH2N(X)CH2CH2NHCOCF2O(CF2CF2O) 12 (CF2O) 12 CF2CONHCH2CH2N(X)CH2CH2CH2Si(OCH3)3 X = -CONHCH2CH2OCOCH=CH2

[0276] Compound (A-2): (CH3O)3SiCH2CH2CH2N(X)CH2CH2NHCOCF2O(CF2CF2O) 12 (CF2O) 12 CF2CONHCH2CH2NHCOCF2O(CF2CF2O) 12 (CF2O) 12 CF2CONHCH2CH2N(X)CH2CH2CH2Si(OCH3)3 X = -CONHCH2CH2OCOCH=CH2

[0277] Component (B): (Meth)acrylic monomer (B-1) Trimethylolpropane Triacrylate (B-2) 1,6-Bis(acryloyloxy)-2,2,3,3,4,4,5,5-octafluorohexane

[0278] Component (C): Radical Polymerization Initiator (C-1) Omnirad MBF (methylbenzoyl formate) (C-2) Cumene Hydroperoxide

[0279] Examples 1 to 6 Components (A) to (C) were mixed at the ratios (weight ratios) shown in Table 1 below to prepare a curable composition. The following evaluations were performed on the obtained curable composition.

[0280] Comparative Example 1 A curable composition was prepared and evaluated in the same manner as in Example 1, except that components (A) to (C) were mixed at the ratios (weight ratios) shown in the following table.

[0281] Comparative Example 2 According to the method described in JP-A-7-188561, a fluoropolyether group-containing compound (A-3) shown below was synthesized. A curable composition was prepared and evaluated in the same manner as in Comparative Example 1, except that the following compound (A-3) was used instead of compound (A-1).

[0282] Compound (A-3): X n (CH3O) 3-n SiCH2CH2CH2NHCOCF2O(CF2CF2O) 12 (CF2O) 12 CF2CONHCH2CH2CH2Si(OCH3) 3-n X n X = (OSiCH3)2CH2OCOCH=CH2) n n = 1.9

[0283] Comparative Example 3 According to the method described in JP-A-10-197731, the fluoropolyether group-containing compound (A-4) shown below was synthesized. A curable composition was prepared and evaluated in the same manner as in Comparative Example 1, except that the following compound (A-4) was used instead of the compound (A-1).

[0284] Compound (A-4): A mixture of the following three types [Chemical formula] [Chemical formula] [Chemical formula]

[0285] <Evaluation> For the curable compositions obtained above, the following evaluations were performed: compatibility evaluation, refractive index measurement, and adhesion test.

[0286] Compatibility evaluation When mixed at the ratios (weight ratios) shown in the following table, it was visually evaluated according to the following criteria whether each composition component was compatible. 〇: Transparent solution ×: Turbid

[0287] Refractive index measurement A small amount of the sample was placed on the prism of an Abbe refractometer, and the refractive index was measured by observing the bright and dark regions generated by the light emitted from the prism at room temperature using the sodium light source D line (589 nm).

[0288] Adhesion test A film with a thickness of 200 μm was formed on the glass using an applicator, and the integrated light quantity was 1000 mJ / cm with a high-pressure mercury lamp 2UV irradiation was performed. Subsequently, it was allowed to stand in an environment of 23°C / 50%RH for 3 days to cure. The cured product thus obtained was cut with a cutter to make 25 grid-shaped cuts at 2-mm intervals, and cellophane tape was pasted thereon and slowly peeled off. The number of residues on the glass of the cured product after peeling was determined, and the adhesion to the glass was evaluated according to the following criteria. 5: No peeling 4: Remaining on the glass for 20 squares or more 3: Remaining on the glass for 15 squares or more 2: Remaining on the glass for 10 squares or more 1: Only 9 squares or less remaining

[0289] [Table 1]

Industrial Applicability

[0290] The curable composition of the present disclosure can be suitably used to form a cured product layer on various substrates.

Claims

1. Component (A): a fluoropolyether group-containing compound, Component (B): a (meth)acrylic monomer, and Component (C): a radical polymerization initiator are included, wherein the fluoropolyether group-containing compound is represented by the following formula (A1) or (A2): 【Chemical 1】 [In the formula: R Ｆ２ is, independently of each other, -Rf ２ ｐ -R Ｆ -O ｑ - and is Rf ２ is an alkylene group which may be substituted by one or more fluorine atoms, １－６ and R Ｆ are each independently a divalent fluoropolyether group, p is 0 or 1, q is independently 0 or 1 respectively, X Ａ each independently represents a single bond or a divalent organic group, X Ｂ is, independently of each other, an (m + 1)-valent group containing a hydrolyzable silyl group, R Ａｃ is, independently of each other, -X Ｄ -X Ｅ (-X Ｆ -OCO-CR ５ =CH ２ ) ｍ’ and is X Ｄ is a single bond or a divalent group, X Ｅ is a single bond or an (m'+1)-valent group, X Ｆ is, independently of each other, a single bond or a divalent group, R ５ is a hydrogen atom, a halogen atom, or a monovalent organic group having 1 to 8 carbon atoms, m' is 1, m is 1, R ａ is, independently of each other, an organic group having a valence of (m3 + 2), m3 is 0, R ｇ is, independently of each other, -NR ｃ CO-R ｅ -, -NR ｃ COO-R ｅ -, or -NR ｃ CONR ｃ -R ｅ -, where these groups are attached on the left side to R ａ and R ｃ is, independently of one another, a hydrogen atom, C １－６ alkyl group, or C ６－１６ aryl group, and R ｅ each independently represents a single bond or a divalent organic group, x is an integer of 1 or more. ] and includes at least one of the compounds represented by the formula, and the content of component (A) is 60% by mass or more based on the total amount of component (A) and component (B), a curable composition.

2. The curable composition according to claim 1, wherein the content of component (A) is 80% by mass or more based on the total amount of component (A) and component (B).

3. R Ｆ each independently represents a formula: -(OC ６ F １２ ) ａ -(OC ５ F １０ ) ｂ -(OC ４ F ８ ) ｃ -(OC ３ R Ｆａ ６ ) ｄ -(OC ２ F ４ ) ｅ -(OCF ２ ) ｆ - [wherein, R Ｆａ is each independently a hydrogen atom, a fluorine atom or a chlorine atom, a, b, c, d, e, and f are each independently an integer from 0 to 200, the sum of a, b, c, d, e, and f is 15 or more, and the order of existence of each repeating unit enclosed in parentheses with a, b, c, d, e, or f attached is arbitrary in the formula, provided that all R Ｆａ is a hydrogen atom or a chlorine atom, at least one of a, b, c, e, and f is 1 or more.] The curable composition according to claim 1, which is a group represented by the formula.

4. R Ｆ each independently represents the following formula (f1), (f2), (f3), (f4), (f5), or (f6): -(OC ３ F ６ ) ｄ -(OC ２ F ４ ) ｅ -(f1) [In the formula, d is an integer of 5 to 200, and e is 0 or 1. ], -(OC ４ F ８ ) ｃ -(OC ３ F ６ ) ｄ -(OC ２ F ４ ) ｅ -(OCF ２ ) ｆ -(f2) [In the formula, c and d are independently integers of 0 to 30; e and f are independently integers of 5 to 200; the sum of c, d, e and f is an integer of 10 to 200; the order of existence of each repeating unit enclosed in parentheses with subscripts c, d, e or f is arbitrary in the formula. ], -(R ６ -R ７ ) ｇ -(f3) [wherein, R ６ is OCF ２ or OC ２ F ４ ; R ７ is a group selected from OC ２ F ４ , OC ３ F ６ , OC ４ F ８ , OC ５ F １０ and OC ６ F １２ or is a combination of two or three groups selected from these groups; g is an integer of 5 to 100. ], -(R ６ -R ７ ) ｇ -R ｒ -(R ７’ -R ６’ ) ｇ’ -(f4) [wherein, R ６ is OCF ２ or OC ２ F ４ and R ７ is a group selected from OC ２ F ４ , OC ３ F ６ , OC ４ F ８ , OC ５ F １０ and OC ６ F １２ or is a combination of two or three groups independently selected from these groups, R ６’ is OCF ２ or OC ２ F ４ and R ７’ is a group selected from OC ２ F ４ , OC ３ F ６ , OC ４ F ８ , OC ５ F １０ and OC ６ F １２ or a combination of two or three groups independently selected from these groups, g is an integer of 3 to 100, g' is an integer of 2 to 100, R ｒ is ​ (In the formula, * indicates the bonding position. ) is. ]; -(OC ６ F １２ ) ａ -(OC ５ F １０ ) ｂ -(OC ４ F ８ ) ｃ -(OC ３ F ６ ) ｄ -(OC ２ F ４ ) ｅ -(OCF ２ ) ｆ -(f5) [In the formula, e is an integer of 5 or more and 200 or less, and a, b, c, d and f are independently integers of 0 or more and 200 or less, and the sum of a, b, c, d, e and f is at least 15, and also, the order of existence of each repeating unit enclosed in parentheses with subscripts a, b, c, d, e or f is arbitrary in the formula. ] -(OC ６ F １２ ) ａ -(OC ５ F １０ ) ｂ -(OC ４ F ８ ) ｃ -(OC ３ F ６ ) ｄ -(OC ２ F ４ ) ｅ -(OCF ２ ) ｆ -(f6) [In the formula, f is an integer of 5 or more and 200 or less, and a, b, c, d and e are independently integers of 0 or more and 200 or less, and the sum of a, b, c, d, e and f is at least 15, and also, the order of existence of each repeating unit enclosed in parentheses with subscripts a, b, c, d, e or f is arbitrary in the formula. ] The curable composition according to claim 1, which is a group represented by the formula.

5. X Ｅ The curable composition according to claim 1, wherein [X] is a single bond.

6. X Ｄ is -O-, -CO-, -COO-, -OCO-, -CONH-, -NHCO-, -OCONH-, -NHCOO-, -NH-CO-NH-, -CH ２ CH(OH)CH ２ -, -CH(CH ２ OH)CH ２ -, -(OSiR １４ ２ ) ｄ５ -, [Chemical 3] [In the formula, * and ** indicate the bonding positions, * is bonded to X Ｂ and ** is bonded to X Ｅ .] and R １４ is a C １－６ alkyl group, or a C ６－１６ aryl group, and d5 is an integer of 1 to 10, the curable composition according to claim 1.

7. X Ｆ is A single bond, C １－６ an alkylene group, -(CH ２ ) ｚ５ -O-(CH ２ ) ｚ６ -(wherein, z5 is an integer from 0 to 6, and z6 is an integer from 0 to 6), or, -(CH ２ ) ｚ７ -phenylene-(CH ２ ) ｚ８ -(wherein, z7 is an integer from 0 to 6, and z8 is an integer from 0 to 6) The curable composition according to claim 1.

8. R ５ The curable composition according to claim 1, wherein R is a hydrogen atom or a methyl group.

9. X Ａ is, independently of one another, a single bond, or -(C α R １１ ２α ) ｓ１ -R １２ ｔ１ - [In the formula: R １１ is each independently a hydrogen atom or a fluorine atom, α is independently an integer of 1 to 10, R １２ is, independently of each other, -O-, -CO-, -NR １０ -, -CONR １０ -, -NR １０ CO-, -COO-, -OCO-, or -OCONH-, and R １０ is a hydrogen atom or a C １－６ alkyl group, s1 is an integer from 0 to 3, t1 is an integer from 0 to 3, the sum of s1 and t1 is 1 or more, the order of existence of each repeating unit enclosed in parentheses with s1 or t1 attached is arbitrary in the formula. ] The curable composition according to claim 1, which is a group represented by

10. X Ａ is - CONR １０ -C α１ H ２α１ -, -(C α２ H ２α２ )-OCONR １０ -, -(C α３ H ２α３ ), or -(C α４ H ２α４ )-O-(C α５ H ２α５ wherein R １０ is a hydrogen atom or a C １－６ alkyl group, α1 is an integer from 1 to 10, α2 is an integer from 1 to 10, α3 is an integer from 1 to 10, α4 is an integer from 0 to 6, α5 is an integer from 0 to 6, The curable composition according to claim 1.

11. X Ｂ is, independently of each other, X Ｂａ (R Ｓｉ ) ｎａ [In the formula: X Ｂａ is, independently of each other, a group having a valence of (m + na + 1), R Ｓｉ is, independently of each other, -X Ｃ -SiR １ ｎ’ R ２ ３－ｎ’ and is X Ｃ is a divalent organic group having 1 to 10 carbon atoms, R １ is, independently of one another, a hydroxyl group or a hydrolyzable group, R ２ is each independently a hydrogen atom or a monovalent organic group, n' is an integer from 1 to 3, na is an integer from 1 to 10. ] The curable composition according to claim 1, which is a group represented by

12. X Ｃ is C １－６ an alkylene group, -(CH ２ ) ｚ１ -O-(CH ２ ) ｚ２ -(wherein, z1 is an integer from 0 to 6, and z2 is an integer from 0 to 6), -(CH ２ ) ｚ３ -phenylene-(CH ２ ) ｚ４ -(wherein, z3 is an integer of 0 to 6, and z4 is an integer of 0 to 6), or -(CH ２ ) ｚ１３ -OCONH-(CH ２ ) ｚ１４ -(wherein, z13 is an integer of 0 to 6, and z14 is an integer of 0 to 6) The curable composition according to claim 11, which is

13. The curable composition according to claim 11, wherein n' is 3.

14. X Ｂａ The curable composition according to claim 11, wherein X is a trivalent group, na is 1, and m is 1.

15. X Ｂａ is N, or 【Chemical Formula 4】 The curable composition according to claim 11, wherein na is 1 and m is 1.

16. Formula (A2) is 【Chemical Formula 5】 [In the formula, R bonded to the N atom located at each end ｂ one of which is RSi and the other is RAc, R Ｓｉ is, independently of each other, -X Ｃ -SiR １ ｎ’ R ２ ３－ｎ’ and X Ｃ is a divalent organic group having 1 to 10 carbon atoms, R １ is, independently of each other, a hydroxyl group or a hydrolyzable group, R ２ is, independently of one another, a hydrogen atom or a monovalent organic group, n' is an integer from 1 to 3, R ｄ each independently represents a single bond or a divalent organic group, R Ｆ２ 、R ａ 、R ｃ 、R Ａｃ 、 m3, and x have the same meanings as described in claim 1. The curable composition according to claim 1, which is

17. R ｄ is, independently of each other, a single bond, or -(CH ２ ) ｚ１７ -NR １０ -(CH ２ ) ｚ１８ -(wherein R １０ is a hydrogen atom or a C １－６ alkyl group, z17 is an integer of 0 to 6, and z18 is an integer of 0 to 6), the curable composition according to claim 16.

18. R ｃ is, independently of each other, a hydrogen atom or a C １－６ alkyl group, and the curable composition according to claim 1.

19. The curable composition according to claim 1, wherein x is an integer from 1 to 5.

20. The curable composition according to claim 1, wherein the fluoropolyether group-containing compound contains a compound represented by formula (A1).

21. The curable composition according to claim 1, wherein the fluoropolyether group-containing compound contains a compound represented by formula (A2).

22. The curable composition according to claim 1, wherein the (meth)acrylic monomer is (a) urethane (meth)acrylate, (b) epoxy (meth)acrylate, (c) polyester (meth)acrylate, (d) polyether (meth)acrylate, (e) silicone (meth)acrylate, or (f) (meth)acrylate monomer.

23. The curable composition according to claim 1, wherein the radical polymerization initiator is diketones, acyloins, acyloin ethers, thioxanthones, benzophenones, acetophenones, quinones, aminobenzoic acids, halogen compounds, acylphosphine oxides, or peroxides.

24. The radical polymerization initiator is benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, thioxanthone, 2,4 - diethylthioxanthone, thioxanthone - 4 - sulfonic acid, benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, acetophenone, 2-(4 - toluenesulfonyloxy)-2 - phenylacetophenone, p - dimethylaminoacetophenone, 2,2'-dimethoxy - 2 - phenylacetophenone, p - methoxyacetophenone, 2 - methyl[4 - (methylthio)phenyl]-2 - morpholino - 1 - propanone, 2 - benzyl - 2 - dimethylamino - 1 - (4 - morpholinophenyl)-butan - 1 - one, anthraquinone, 1,4 - naphthoquinone, ethyl 2 - dimethylaminobenzoate, ethyl 4 - dimethylaminobenzoate, (n - butoxy)ethyl 4 - dimethylaminobenzoate, isoamyl 4 - dimethylaminobenzoate, 2 - ethylhexyl 4 - dimethylaminobenzoate, phenacyl chloride, trihalomethylphenyl sulfone, acylphosphine oxide, or di - t - butyl peroxide, methyl benzoylformate, 1 - hydroxy - cyclohexyl - phenyl - ketone, 1 - [4 - (2 - hydroxyethoxy)-phenyl]-2 - hydroxy - 2 - methyl - 1 - propan - 1 - one, 2 - hydroxy - 1 - {4 - [4 - (2 - hydroxy - 2 - methyl - propionyl)-benzyl]phenyl}-2 - methyl - propan - 1 - one, 2 - methyl - 1 - (4 - methylthiophenyl)-2 - morpholinopropan - 1 - one, 2 - benzyl - 2 - dimethylamino - 1 - (4 - morpholinophenyl)-1 - butanone, 2 - (dimethylamino)-2 - [(4 - methylphenyl)methyl]-1 - [4 - (4 - morpholinyl)phenyl]-1 - butanone, bis(2,4,6 - trimethylbenzoyl)-phenylphosphine oxide, bis(η5 - 2,4 - cyclopentadien - 1 - yl)-bis(2,6 - difluoro - 3 - (1H - pyrrol - 1 - yl)-phenyl)titanium, 1,2 - octanedione, 1 - [4 - (phenylthio)-,2-(O - benzoyloxime)], ethanone,The curable composition according to claim 1, which is 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(0-acetyloxime), 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide, t-butyl hydroperoxide, cumene hydroperoxide, diisopropylbenzene hydroperoxide, permentahydroperoxide, or t-methylbutyl hydroperoxide.,

25. The curable composition according to claim 1, further containing a solvent.

26. A cured product obtained from the curable composition according to any one of claims 1 to 25.

27. An article comprising a substrate and a layer formed from the curable composition according to any one of claims 1 to 25 on the surface of the substrate.

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