Hardening composition

Abstract

To provide a curable composition excellent in alcohol resistance.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 excellent in alcohol resistance.

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 is a hydrogen atom or a methyl group. The curable composition according to any one of [1] to [9] above.

[11] 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-, -NR 10 -, -CONR 10 -, -NR 10It is 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] wherein n' is 3.

[17] X Ba is a trivalent group, n is 1, and m is 1, the curable composition according to

[14] above.

[18] X Ba is N, or -C(-O-)-, n is 1, and m is 1, the curable composition according to

[14] above.

[19] Formula (A2) is

Chemical formula

[18] above.

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

[19] .

[21] R d Each independently represents a single bond 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). The curable composition according to the above

[19] .

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

[21] .

[23] R a’ Each independently represents a trivalent group that 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)-, or carbon-carbon atoms. The curable composition according to the above

[22] .

[24] k is 1 or 2. The curable composition according to the above

[22] .

[25] R c Each independently represents a hydrogen atom or a C 1-6 alkyl group. The curable composition according to any one of the above [1] to

[24] .

[26] x is an integer from 1 to 5. The curable composition according to any one of the above [1] to

[25] .

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

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

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

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

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

[28] above, 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.

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

[29] above, wherein the radical polymerization initiator is diketones, acyloins, acyloin ethers, thioxanthones, benzophenones, acetophenones, quinones, aminobenzoic acids, halogen compounds, acylphosphine oxides, or peroxides.

[31] 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 any one of [1] to

[30] above, 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.,

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

[31] above, further containing a solvent.,

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

[32] above.,

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

[32] above on the surface of the substrate., [Effect of the Invention]

[0006] According to the present disclosure, a curable composition excellent in alcohol resistance can be provided., [Embodiments for Carrying Out the Invention]

[0007] As used herein, the "monovalent organic group" means a monovalent group containing carbon. The monovalent organic group is not particularly limited, and may be a hydrocarbon group or a derivative thereof. The derivative of the hydrocarbon group means a group having one or more N, O, S, Si, amide, sulfonyl, siloxane, carbonyl, carbonyloxy, etc. at the terminal or in the molecular chain of the hydrocarbon group. Incidentally, when simply indicated as an "organic group", it means a monovalent organic group. The "divalent organic group" means a divalent group containing carbon. Examples of such a divalent organic group include a divalent group obtained by further removing one hydrogen atom from the organic group. Similarly, a trivalent or higher organic group means a group obtained by removing a predetermined number of hydrogen atoms from the organic group.,

[0008] As used herein, the term "hydrocarbon group" means a group containing carbon and hydrogen, which is a group obtained by removing a hydrogen atom from a hydrocarbon. Such a hydrocarbon group is not particularly limited, but includes, for example, a C 1-20 hydrocarbon group, such as an aliphatic hydrocarbon group, an aromatic hydrocarbon group, etc. The above-mentioned "aliphatic hydrocarbon group" may be linear, branched or cyclic, and may be saturated or unsaturated. Further, 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 substituents of the "hydrocarbon group" are not particularly limited, but include, for example, a halogen atom, a C 1-6 alkyl group which may be substituted with one or more halogen atoms, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 3-10 cycloalkyl group, a C 3-10 unsaturated cycloalkyl group, a 5- to 10-membered heterocyclyl group, a 5- to 10-membered unsaturated heterocyclyl group, a C 6-10 aryl group and one or more groups selected from a 5- to 10-membered heteroaryl group.

[0010] As used herein, the term "hydrolyzable group" means a group capable of undergoing a hydrolysis reaction, that is, a group capable of detaching from the main skeleton of a compound by a hydrolysis reaction. Examples of the hydrolyzable group include -OR j 、-OCOR j 、-O-N=CR j 2、-NR j 2、-NHR j 、-NCO、-NCO, or a halogen (in these formulas, R j represents a substituted or unsubstituted C 1-4 alkyl group).

[0011] The curable composition of the present disclosure is Component (A): a fluoropolyether group-containing compound, Component (B): (Meth)acrylic monomer, and Component (C): Radical polymerization initiator contains

[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 by containing 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):

Chemical formula

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

[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 1-6 alkylene group which may be substituted by one or more fluorine atoms.

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

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

[0023] The above C 1-6 The perfluoroalkylene group may be linear or branched, preferably a linear or branched C 1-3 is a 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 of each other, 0 or 1. 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 becomes relatively low, and the coating property and handleability 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 are each independently an integer from 0 to 200, and the sum of a, b, c, d, e, and f is 1 or more. The order of existence of each repeating unit enclosed in parentheses with a, b, c, d, e, or f is arbitrary in the formula. However, when 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.] is a group represented by.

[0029] R Fa is preferably a hydrogen atom or a fluorine atom, more preferably a fluorine atom. However, when 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.

[0030] a, b, c, d, e, and f may preferably each independently be an integer from 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, still more preferably 60 or less, and may be, for example, 50 or less or 30 or less.

[0032] These repeating units may be linear, branched, or may contain a ring structure. For example, -(OC6F 12 )- may be -(OCF2CF2CF2CF2CF2CF2)-, -(OCF(CF3)CF2CF2CF2CF2)-, -(OCF2CF(CF3)CF2CF2CF2)-, -(OCF2CF2CF(CF3)CF2CF2)-, -(OCF2CF2CF2CF(CF3)CF2)-, -(OCF2CF2CF2CF2CF(CF3))-, etc. -(OC5F 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 aspect, the repeating unit is branched.

[0038] In one aspect, R F is, independently of each other, a group represented by any one 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 subscripts 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 7is 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, 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, g is an integer from 2 to 100, g’ is an integer from 2 to 100, R r is

Chemical 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-, -OC2F4OC2F4OC3F6-, -OC2F4OC2F4OC4F8-, -OC2F4OC3F6OC2F4-, -OC2F4OC3F6OC3F6-, -OC2F4OC4F8OC2F4-, -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 linear or branched, preferably linear. In this embodiment, the above formula (f3) is preferably -(OC2F4-OC3F6) g - or -(OC2F4-OC4F8) g -.

[0042] In the above formula (f4), R 6 , R 7 and g have the same meanings as described in the above formula (f3) and have similar embodiments. R 6’ , R 7’ and g' are respectively the same as R 6 , R 7 and g described in the above formula (f3) and have similar embodiments. R r is preferably

Chemical formula

Chemical formula

[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 aspect, the above R F is a group represented by the above formula (f1) or (f2).

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

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

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

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

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

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

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

[0053] The above R F In, 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 embodiment, the above e / f ratio is preferably 0.2 to 0.95, more preferably 0.2 to 0.9.

[0055] In one embodiment, 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 as follows.

[0058] Said 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-, -CH2CH(OH)CH2-, -CH(CH2OH)CH2-, -(OSiR 14 2) d5 -,

Chemical formula

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

[0061] Said 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 is -X G -X H [Wherein: 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, 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 from 0 to 6, for example, an integer from 1 to 6, and z6 is an integer from 0 to 6, for example, an integer from 1 to 6), or -(CH2) z7 -phenylene-(CH2) z8 -(wherein, z7 is an integer from 0 to 6, for example, an integer from 1 to 6, and z8 is an integer from 0 to 6, for example, an integer from 1 to 6) is. These groups may be substituted by one or more substituents selected from, for example, a fluorine atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, and a C 2-6 alkynyl group, but are 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] s 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.] It is a group represented by. In the formula, the left side is R F2 is bonded to.

[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 -.

[0082] The above R 11 is preferably a hydrogen atom.

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

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

[0085] The above R 10 is a hydrogen atom or a C 1-6 alkyl group, preferably a hydrogen atom.

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

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

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

[0089] In a more preferred embodiment, 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 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. Such a group is bonded to R F2 on the left side.

[0090] X A is preferably —CONH—C α H 2α —. Such a group is bonded to R F2 on the left side.

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

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

[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, a (m + 1)-valent group. However, in each formula, at least one X B is a (m + 1)-valent group containing a hydrolyzable silyl group.

[0097] In one embodiment, X B is, independently of each other, a (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, a (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] The above R Si is, independently of each other, -X C -SiR 1 n’ R 2 3-n’ is as follows.

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

[0103] In one embodiment, X C is 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) is as follows. These groups may be substituted with one or more substituents selected from, for example, a fluorine atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, and a C 2-6 alkynyl group, but are preferably unsubstituted. These groups are bonded to the left side to X B is bonded.

[0104] The above C 1-6 alkylene group may be linear or branched, but is preferably linear.

[0105] In a preferred embodiment, X C is a C 1-6 alkylene group, preferably a C 2-4 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 (that is, an alkoxy group). R h includes 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 preferred, and a methyl group or an ethyl group is more preferred. In one aspect, R h is a methyl group, and in another aspect, 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 even more preferably a methyl group.

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

[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 above X Ba is a trivalent group, preferably

Chemical formula

[0114] In a preferred embodiment, X Ba is N. In this case, in the formula, m is 1 and n is 1.

[0115] In another embodiment, X B is 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, preferably, -X Bb -SiR 1 nb R sb 4-nb [Wherein: 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 embodiment, k is an integer from 1 to 4.

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

[0126] In one embodiment, k is 1.

[0127] In one embodiment, k is 2.

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

[0129] In a preferred embodiment, R a’ is each independently a trivalent group that 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-)-, carbon-carbon atoms

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

Chemical formula

[0131] In one embodiment, R a’ is N.

[0132] In one embodiment, 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 embodiment, 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.) Such a C 1-20 alkylene group may be linear or branched, but is preferably linear. Such a C 1-20 alkylene group is preferably a C 1-10 alkylene group, more preferably a C 1-6 alkylene group, even 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, even more preferably an integer of 1 or more and 5 or less, for example, an integer of 2 or more and 10 or less, even 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, independently of each other, 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 on the left side F2 .

[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 as follows. These groups may be substituted by one or more substituents selected from, for example, a fluorine atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, and a 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 to 2×10 5 . Among such ranges, 2×10 3 to 1×105 , more preferably having a number average molecular weight of 3×10 3 ~2×10 4 is preferable from the viewpoint of wear durability. The "number average molecular weight" is 19 a value measured by F-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 and 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, and Br-Mg-CH2CH=CH2 are reacted to obtain (CH2=CHCH2)2(HO)C-R F2 -C(OH)(CH2CH=CH2)2 A compound represented by the following. Then, the above compound and the following formula: HSiR 1 n’ R 2 3-n’ are reacted 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. Next, 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., and R 35 is a divalent group.) can be obtained by reacting with a compound represented by the following.

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

Chemical formula

Chemical formula

Chemical formula

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

Chemical formula

Chemical formula

Chemical formula

[0172] In one embodiment, 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 of 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 of 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, 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: Then, the obtained compound is reacted with 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: a compound represented by formula (A2) can be obtained.

[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 to obtain 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 are as defined in the description of formula (A2).] Then, react the obtained compound with NH2-R 9‘ -NH2 [wherein, R 9‘ is as defined in the description of R 9 .] to react with 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 are as defined in the description of formula (A2), and R 9‘ is as defined in the description of R 9 .] 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’ 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 -(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: Next, the obtained compound is reacted with 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 formula (A2), a compound represented by the formula (A2) can be obtained.

[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. In addition, 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]

Chem.

[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] Component (C): Radical polymerization initiator

[0183] The above radical polymerization initiator can preferably be a radical photoinitiator. Examples of radical photoinitiators 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, and the like.

[0184] 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.,

[0185] 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-hydrodoxy-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), OMNIRAD261, OMNIRAD369, OMNIRAD500, DAROCUR 1173: 2-Hydroxy-2-methyl-1-phenyl-propan-1-one, DAROCUR TPO: 2,4,6-Trimethylbenzoyl-diphenyl-phosphine oxide, DAROCUR1116, DAROCUR2959, DAROCUR1664, DAROCUR4043, 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.

[0186] The content of component (A) is preferably 5.0% by mass or less, for example 4.0% by mass or less, 3.0% by mass or less, or 1.0% by mass or less, based on the total amount of component (A) and component (B).

[0187] The content of component (A) is preferably 0.1% by mass or more, for example 0.5% by mass or more, or 1.0% by mass or more, based on the total amount of component (A) and component (B).

[0188] The content of component (A) is preferably 0.1 to 5.0% by mass, for example 1.0 to 5.0% by mass, 0.1 to 4.0% by mass, 0.1 to 3.0% by mass, 1.0 to 4.0% by mass, or 1.0 to 3.0% by mass, based on the total amount of component (A) and component (B).

[0189] By containing component (A) and component (B), especially in the above ratios, the curable composition of the present disclosure gives a cured product with excellent adhesion. Further, the obtained cured product has high chemical resistance, especially high alcohol resistance.

[0190] Component (C) is preferably contained in an amount of 0.1 to 20 parts by mass, more preferably 1 to 10 parts by mass, and still more preferably 1 to 5 parts by mass, based on 100 parts by mass in total of the above component (A) and component (B).

[0191] The curable composition of the present disclosure may contain a solvent.

[0192] 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.

[0193] In a preferred embodiment, the solvent is an alcohol, a hydrofluoroether, or a mixed solvent of two or more of these.

[0194] Examples of the aliphatic hydrocarbons include hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, mineral spirit, etc.

[0195] Examples of the aromatic hydrocarbons include benzene, toluene, xylene, naphthalene, solvent naphtha, etc.

[0196] 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.

[0197] Examples of the ketones include acetone, methyl ethyl ketone, methyl isobutyl ketone, 2-hexanone, cyclohexanone, methyl aminoketone, 2-heptanone, etc.

[0198] 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.

[0199] Examples of the above-mentioned alcohols include methanol, ethanol, iso-propanol, n-butanol, isobutanol, tert-butanol, sec-butanol, 3-pentanol, octyl alcohol, 3-methyl-3-methoxybutanol, tert-amyl alcohol and the like. The alcohols are preferably methanol, ethanol, and iso-propanol.

[0200] Examples of the above-mentioned glycols include ethylene glycol, propylene glycol and the like.

[0201] Examples of the above-mentioned cyclic ethers include tetrahydrofuran, tetrahydropyran, dioxane and the like.

[0202] Examples of the above-mentioned amides include N,N-dimethylformamide, N,N-dimethylacetamide and the like.

[0203] Examples of the above-mentioned ether alcohols include methyl cellosolve, cellosolve, isopropyl cellosolve, butyl cellosolve, diethylene glycol monomethyl ether and the like.

[0204] Examples of the above-mentioned perfluoroaliphatic hydrocarbons having 5 to 12 carbon atoms include perfluorohexane, perfluoromethylcyclohexane, perfluoro-1,3-dimethylcyclohexane and the like.

[0205] Examples of the above-mentioned polyfluoroaromatic hydrocarbons include bis(trifluoromethyl)benzene and the like.

[0206] Examples of the above-mentioned 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.) and the like.

[0207] Examples of the hydrofluorocarbon (HFC) include 1,1,1,3,3-pentafluorobutane (HFC-365mfc).

[0208] 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).

[0209] Examples of the hydrofluoroether (HFE) include alkyl perfluoroalkyl ethers (the perfluoroalkyl group and the alkyl group may be linear or branched) 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), and CF3CH2OCF2CHF2 (e.g., Asahiklin (registered trademark) AE-3000 manufactured by Asahi Glass Co., Ltd).

[0210] 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 of these.

[0211] The content of the above solvent can be preferably 20 to 90% by mass, more preferably 40 to 90% by mass, based on the total amount of components (A) to (C).

[0212] 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, a surfactant, a polymerization inhibitor, a sensitizer, a UV fluorescent agent, etc.

[0213] 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 C 1-16 perfluoroalkyl group), a fluorine atom or a hydrogen atom, and Rf 5 and Rf 6 are more preferably each independently a C 1-3 perfluoroalkyl group. a', b', c' and d' each represent four types of repeating unit numbers of perfluoro(poly)ethers that constitute the main skeleton 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)-.

[0214] The above ring structure is the following three-membered ring or four-membered ring:

Chemical formula

[0215] For example, (OC4F8) is

Chemical formula

[0216] Examples of the perfluoro(poly)ether compound represented by the 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). 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.

[0217] From another perspective, the fluorinated oil may be a compound represented by the general formula Rf 3 -F (wherein Rf 3 is a C 5-16 perfluoroalkyl group). It may also be a chlorotrifluoroethylene oligomer.

[0218] The 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.

[0219] The fluorine-containing oil can be contained in the curable composition of the present disclosure in an amount of, for example, 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 substantially does not contain a fluorine-containing oil. Substantially not containing a fluorine-containing oil means that it may contain no fluorine-containing oil or may contain an extremely small amount of fluorine-containing oil.

[0220] 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 or 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 a 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.

[0221] In the curable composition of the present disclosure, such a silicone oil can 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).

[0222] 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.

[0223] 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.

[0224] The above catalysts may be added to the curable composition immediately before use.

[0225] The above catalysts may be additionally added to the curable composition immediately before use according to the method of use.

[0226] The above catalysts may be contained preferably 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 with respect to 100 parts by mass in total of the above components (A) and (B).

[0227] 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.

[0228] The above alcohol is preferably methanol, ethanol, 2,2,3,3,3-pentafluoro-1-propanol or 2,2,2-trifluoroethanol.

[0229] 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.

[0230] The viscosity of the curable composition of the present disclosure may 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 may 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.

[0231] In one aspect, the viscosity of the curable composition of the present disclosure may preferably be 100 to 5000 mPa·s, more preferably 500 to 3000 mPa·s, and even more preferably 1000 to 2000 mPa·s.

[0232] (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.

[0233] Also, 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.

[0234] 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 bonding part between a housing and a printed circuit board, or the gap between a resin-molded metal terminal part and a molding resin).

[0235] 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 electrical and electronic components and in-vehicle components. Since the curable composition of the present disclosure has a good elastic modulus particularly even 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.

[0236] 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.

[0237] 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.

[0238] 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.

[0239] 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 (such as 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.

[0240] In a preferred embodiment, the substrate can be glass, resin, polarizing plate, OCA (Optical Clear Adhesive), or metal.

[0241] Examples of the glass include sapphire glass, soda-lime glass, alkali aluminosilicate glass, borosilicate glass, non-alkali glass, crystal glass, and quartz glass, with chemically strengthened soda-lime glass, chemically strengthened alkali aluminosilicate glass, and chemically bonded borosilicate glass being particularly preferred.

[0242] The shape of the substrate is not particularly limited and may be, for example, plate-shaped, film, or other forms. Also, the surface area of the substrate on which the cured product layer is to be formed may be at least a part of the substrate surface and can be appropriately determined according to the use and specific specifications of the article to be manufactured.

[0243] 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 substrate, post-treating this layer as necessary, and thereby forming a layer from the curable composition of the present disclosure.

[0244] 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 substrate 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.

[0245] 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.

[0246] In a preferred embodiment, the article of the present disclosure can be an electric and electronic component, an in-vehicle component, an automotive member (e.g., a sealing material, specifically, a gasket), a chemical plant, a semiconductor manufacturing apparatus, etc.

[0247] Also, the article of the present disclosure may be a medical device or a medical material.

[0248] 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. Also, 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.

[0249] As described above in detail are the curable composition, cured product, and article of the present disclosure. Note that these of the present disclosure are not limited to those exemplified above.

Examples

[0250] Hereinafter, the compounds of the present disclosure will be described in examples, but the present disclosure is not limited to the following examples. Note that in these examples, the order of the repeating units constituting the fluoropolyether is arbitrary, and the chemical formulas shown below represent the average composition.

[0251] 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

[0252] Compound (A-2): (CH3O)3SiCH2CH2CH2N(X)CH2CH2NHCOCF2O(CF2CF2O) 12 (CF2O) 12 CF2CONHCH2CH2NHCOCF2O(CF2CF2O) 12 (CF2O) 12 CF2CONHCH2CH2N(X)CH2CH2CH2Si(OCH3)3 X = -CONHCH2CH2OCOCH=CH2

[0253] Component (B): (Meth)acrylic monomer (B-1) Beam set 575CB (manufactured by Arakawa Chemical Industries, Ltd.)

[0254] Component (C): Radical polymerization initiator (C-1) Omnirad 184

[0255] Examples 1 - 5 Components (A) - (C) were mixed at the ratios (weight ratios) shown in Table 1 below to prepare a curable composition. The obtained curable composition was formed into a film with a thickness of 200 μm on glass using an applicator, and UV irradiation with an integrated light amount of 1000 mJ / cm 2 was performed using a high-pressure mercury lamp. Then, it was allowed to stand for 3 days in an environment of 23°C / 50%RH for curing, and the following evaluations were carried out.

[0256] Comparative Example 1 A surface treatment layer was formed in the same manner as in Example 1, except that Optool DAC-HP (manufactured by Daikin Industries, Ltd.) (A-3) was used instead of compound (A-1).

[0257] Comparative Example 2 According to the method described in JP-A-7-188561, the following fluoropolyether group-containing acrylic compound (A-4) was synthesized. A surface treatment layer was formed in the same manner as in Comparative Example 1, except that the following compound (A-4) was used instead of compound (A-3). Compound (A-4): X n (CH3O) 3-n SiCH2CH2CH2NHCOCF2O(CF2CF2O) 12 (CF2O) 12 CF2CONHCH2CH2CH2Si(OCH3) 3-n X n X=(OSiCH3)2CH2OCOCH=CH2) n n = 1.9

[0258] 〈Evaluation〉 Regarding the substrates with the surface treatment layers obtained above, the following evaluations of static contact angle, eraser rubber abrasion durability test, and alcohol resistance test were carried out respectively.

[0259] Static contact angle The static contact angle was measured by the following method using a fully automatic contact angle meter DropMaster700 (manufactured by Kyowa Interface Science Co., Ltd.). 3 μL of the test liquid was dropped from a microsyringe onto a horizontally placed substrate, and the static image 1 second after the drop was taken with a video microscope to obtain the static contact angle. Regarding the measured values of the static contact angle of the test liquid, five points with different surface treatment layers of the substrate were measured, and the average value was calculated and used.

[0260] Criteria for judging the static contact angle of water 〇: Contact angle of 108 degrees or more ×: Contact angle less than 108 degrees

[0261] Eraser wear durability test Regarding the cured films shown in Table 〇 below, the wear durability was evaluated by an eraser wear durability test. Specifically, a sample article with a surface treatment layer was horizontally placed, and an eraser (manufactured by Minoan, hardness 81 (Durometer A type), circular with a planar dimension of 0.6 cm in diameter) was brought into contact with the surface of the surface treatment layer, and a load of 1000 gf was applied thereon. Then, with the load applied, the eraser was reciprocated at a speed of 48 mm / second (friction speed 40 rpm). The static contact angle (degrees) of water was measured every 1000 reciprocations. The evaluation was terminated when the measured value of the contact angle became less than 95 degrees. Finally, the number of reciprocations when the contact angle exceeded 95 degrees was evaluated.

[0262] Alcohol resistance test In the alcohol resistance test, cotton was attached to a jig of 1 cm square, and a wear test of 5000 cycles was carried out at a speed of 60 cycles / minute with a load of 1000 gf in a state where ethanol was impregnated. The static contact angle of water after wear was evaluated according to the following criteria.

[0263] Criteria for judging the static contact angle of water 〇: Contact angle of 108 degrees or more ×: Contact angle less than 108 degrees

[0264]

Table 1

Industrial Applicability

[0265] The curable composition of the present disclosure can be suitably used to form a cured product layer on a wide variety of base materials.

Claims

1. Component (A): a fluoropolyether group-containing compound, Component (B): a (meth)acrylic monomer, and Component (C): a radical polymerization initiator comprising, 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 Rf ２ is an optionally substituted C １－６ alkylene group, R Ｆ is, independently of one another, a divalent fluoropolyether group, p is 0 or 1, q is independently 0 or 1, X Ａ each independently represents a single bond or a divalent organic group, X Ｂ each independently represents 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 each independently represents 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 one another, 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, a C １－６ alkyl group, or a 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 contains at least one of the compounds represented by the formula, The content of component (A) is 5.0% by mass or less based on the total amount of component (A) and component (B), a curable composition.

2. The content of component (A) is 0.1 to 5.0% by mass based on the total amount of component (A) and component (B), the curable composition according to claim 1.

3. R Ｆ is, independently, of the 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.] a group represented by the formula, the curable composition according to claim 1.

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 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 is 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, 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, g is an integer of 3 to 100, g' is an integer of 2 to 100, R ｒ is 【Chemical 2】 (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 further, 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 further, 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. ] a group represented by the formula, the curable composition according to claim 1.

5. X Ｅ The curable composition according to claim 1, wherein Ｅ 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 Formula 3] [In the formula, * and ** indicate 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) is, 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 each other, a single bond, or -(C α R １１ ２α ) ｓ１ -R １２ ｔ１ - [In the formula: R １１ each independently is a hydrogen atom or a fluorine atom, α is independently an integer of 1 to 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, and 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 and R １０ is a hydrogen atom or a C １－６ alkyl group, and 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 each other, a hydroxyl group or a hydrolyzable group, R ２ Each independently represents 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. n' is 3, The curable composition according to claim 11.

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, one of Rb bonded to the N atom located at each end 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 each independently represents a hydroxyl group or a hydrolyzable group, R ２ each independently represents 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 one another, 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 from 0 to 6, and z18 is an integer from 0 to 6), the curable composition according to claim 16.

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

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

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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