Fluorine-containing ether compounds, fluorine-containing ether compositions, coating solutions, articles, and methods for manufacturing articles.

Abstract

To provide a fluorine-containing ether compound, a fluorine-containing ether composition and a coating liquid excellent in chemical resistance, an article having a surface layer excellent in chemical resistance and a method for producing the same, and a method for producing a fluorine-containing ether compound excellent in chemical resistance.SOLUTION: Provided is a fluorine-containing ether compound that has a first partial structure represented by the following formula (1) and a second partial structure represented by the following formula (2), and that has at least five first partial structures, or has at least two second partial structures: -ORf12- (1), -ORf13- (2), wherein Rf12 is a C1-6 fluoroalkylene group, and Rf13 is a group having a fluorine-containing cyclic structure which may have a hetero atom.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to fluorine-containing ether compounds, fluorine-containing ether compositions, coating solutions, articles, methods for producing articles, and methods for producing fluorine-containing compounds. [Background technology]

[0002] Fluorine-containing ether compounds have excellent properties such as low refractive index, low dielectric constant, water and oil repellency, heat resistance, chemical resistance, chemical stability, and transparency, and are used in a wide variety of fields, including electrical and electronic materials, semiconductor materials, optical materials, and surface treatment agents. For example, fluorine-containing ether compounds having a perfluoropolyether chain and a hydrolyzable silyl group can form a surface layer on the substrate surface that exhibits high lubricity, water repellency, and oil repellency, making them suitable for use as surface treatment agents. Surface treatment agents containing fluorine-containing ether compounds are used in applications where it is required that the surface layer maintains its water repellency and oil repellency even after repeated friction with fingers (friction resistance) and that fingerprints adhering to the surface layer can be easily removed by wiping (fingerprint stain removal) for a long period of time, such as components that make up the surface touched by fingers on touch panels, eyeglass lenses, and displays of wearable devices.

[0003] As a fluorine-containing ether compound that can form a surface layer on the surface of a substrate that has excellent abrasion resistance and fingerprint stain removal properties, a fluorine-containing ether compound having a perfluoropolyether chain and a hydrolyzable silyl group has been proposed (Patent Documents 1 and 2). [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2016-037541 [Patent Document 2] International Publication No. 2017 / 038830 [Overview of the project] [Problems that the invention aims to solve]

[0005] As described above, fluorine-containing ether compounds are useful as surface treatment agents for imparting the various physical properties mentioned above, and there is a growing demand for fluorine-containing ether compounds that can be used in a variety of environments. Therefore, there is a need for fluorine-containing ether compounds with even better chemical resistance.

[0006] The present invention aims to provide a fluorine-containing ether compound with excellent chemical resistance, a fluorine-containing ether composition and coating liquid capable of forming a surface layer with excellent chemical resistance, an article having a surface layer with excellent chemical resistance and a method for producing the same, and a method for producing a fluorine-containing compound useful as a raw material for the fluorine-containing ether compound. [Means for solving the problem]

[0007] The present invention provides a fluorine-containing ether compound, a fluorine-containing ether composition, a coating liquid, an article, a method for producing the same, and a method for producing a fluorine-containing compound, having the following configurations [1] to

[25] . [1] A fluorine-containing ether compound having a first substructure represented by the following formula (1) and a second substructure represented by the following formula (2), A fluorine-containing ether compound characterized by having five or more of the first substructure, or two or more of the second substructure. -OR f12 - (1) -OR f13 - (2) however, R f12 This is a fluoroalkylene group having 1 to 6 carbon atoms. R f13 This is a group having a fluorine-containing ring structure, which may contain heteroatoms.

[0008] [2] A fluorine-containing ether compound of [1], which is represented by the following formula (1A). [R f -] a1 Q 1[-T] b1 (1A) However, R f has the first partial structure and the second partial structure, and is a monovalent group with a carbon atom at the bonding end having five or more of the first partial structures or two or more of the second partial structures, where R f when there are two or more, the two or more R f may be the same or different, Q 1 is a single bond or a (a1 + b1)-valent linking group, T is -R f6 , -Ar, -OR 10 , -SR 10 , -NOR 10 , -C(=O)R 10 , -N(R 10 )2, -N + (R 10 )3X 3 , -C≡N, -C(=NR 10 )-R 10 , -N + ≡N, -N=NR 10 , -C(=O)OR 10 , -C(=O)OX 2 , -C(=O)OX 4 , -C(=O)OC(=O)R 10 , -SO2R 10 , -SO3H, -SO3X 2 , -O-P(=O)(-OR 10 )2, -O-P(=O)(-OR 10 )(-OX 2 ), -N=C=O, -Si(R) 3-c (L) c , -C(R 10 )=C(R 10 )2, -C≡C(R 10 ), -C(=O)N(R 10 )2, -N(R 10 )C(=O)R 10 , -Si(R 10 )2-O-Si(R 10 )3, -NH-C(=O)R 10 , -C(=O)NHR 10 , -I, [ka] R f6 These are fluoroalkyl groups having 1 to 6 carbon atoms. R 10 R is a hydrogen atom, a C1-C6 alkyl group or fluoroalkyl group, or an aryl group which may have substituents. 10 If there are 2 or more, then 2 or more R 10 They may be the same or different from each other. Ar is an aryl group which may have substituents. X 2 These are alkali metal ions or ammonium ions, X 3 It is a halide ion, X 4 It is a halogen atom, R is an alkyl group, L is a hydrolyzable group or a hydroxyl group, and the two or more Ls in T may be the same or different. a1 is an integer greater than or equal to 1. b1 is an integer greater than or equal to 1. c is 2 or 3, If there are two or more T's, the two or more T's may be the same or different.

[0009] [3] The aforementioned R f However, the group is represented by the following formula (g1a), which is the fluorine-containing ether compound of [2]. R f1 -(OR f2 ) m (OR f3 ) n - (g1a) however, R f1 This is a fluoroalkyl group having 1 to 20 carbon atoms, or a monovalent fluorinated hydrocarbon group having a fluorine-containing ring structure. R f2 This is a fluoroalkylene group having 1 to 6 carbon atoms (however, Q 1 R that joins f2 Q1 At least one fluorine atom is bonded to the carbon atom at the terminal end of the side. R f3 This refers to a divalent fluorinated hydrocarbon group having a fluorine-containing ring structure (however, Q 1 R that joins f3 Q 1 At least one fluorine atom is bonded to the carbon atom at the terminal end of the side. n is R f1 If it has a fluorine-containing ring structure, it is an integer from 0 to 500, R f1 If it does not have a fluorine-containing ring structure, it is an integer from 1 to 500, and if n is 2 or greater, (OR f3 ) n is two or more ORs f3 It may consist of, When n is 0, m is an integer between 5 and 500. When n is 1 or greater, m is an integer between 2 and 500. If m is 2 or greater, (OR f2 ) m is two or more ORs f2 It may consist of, m pieces (OR f2 ) and n (OR f3 The order of joining the elements is not restricted.

[0010] [4] Q 1 A fluorine-containing ether compound of [2] or [3], wherein the group is represented by formula (g2-1) (where a1=d1+d3 and b1=d2+d4), formula (g2-2) (where a1=e1 and b1=e2), formula (g2-3) (where a1=1 and b1=2), formula (g2-4) (where a1=h1 and b1=h2), formula (g2-5) (where a1=i1 and b1=i2), formula (g2-6) (where a1=1 and b1=1), or formula (g2-7) (where a1=1 and b1=i3). [ka] (-AQ12 -) e1 C(R 2 ) 4-e1-e2 (-Q 22 -) e2 (g2-2) -A-Q 13 -N(-Q 23 -)2(g2-3) (-A-Q 14 -) h1 Z(-Q 24 -) h2 (g2-4) (-A-Q 15 -) i1 Si(R 3 ) 4-i1-i2 (-Q 25 -) i2 (g2-5) -A-Q 26 - (g2-6) -A-Q 12 -CH(-Q 22 -)-Si(R 3 ) 3-i3 (-Q 25 -) i3 (g2-7) However, In formulas (g2-1) to (g2-7), the A side is connected to R f , and the Q 22 , Q 23 , Q 24 , Q 25 and Q 26 sides are connected to T, A is a single bond, -C(O)NR 6 -, -C(O)-, -OC(O)O-, -NHC(O)O-, -NHC(O)NR 6 -, -O- or -SO2NR 6 -, Q 11 is a single bond, -O-, an alkylene group, or a group having -C(O)NR 6 -, -C(O)-, -NR 6 - or -O- between carbon-carbon atoms of an alkylene group having 2 or more carbon atoms, Q 12 is a single bond, an alkylene group, or a group having -C(O)NR 6-, -C(O)-, -NR 6 A group having - or -O-, Q 1 Q 12 If you have 2 or more Q 12 They may be the same or different. Q 13 This refers to a single bond (where A is -C(O)-), an alkylene group, and an -C(O)NR between carbon atoms of an alkylene group with 2 or more carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O-, or a group having -C(O)- at the N-side terminal of an alkylene group, Q 14 Q 14 If the atom at Z to which the bond is formed is a carbon atom, then Q 12 Q 14 If the atom at Z to which it is bonded is a nitrogen atom, then Q 13 Q 1 Q 14 If you have 2 or more Q 14 They may be the same or different. Q 15 This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between the carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O-, Q 1 Q 15 If you have 2 or more Q 15 They may be the same or different. Q 22 This refers to alkylene groups, and alkylene groups with 2 or more carbon atoms, where the -C(O)NR is formed between the carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O-, or -C(O)NR at the non-T-connected end of the alkylene group. 6 -, -C(O)-, -NR 6 - or -O- groups, or alkylene groups having 2 or more carbon atoms with -C(O)NR between carbon atoms. 6 -, -C(O)-, -NR 6 - or -O- and -C(O)NR at the end that is not connected to T 6-, -C(O)-, -NR 6 A group having - or -O-, Q 1 Q 22 If you have 2 or more Q 22 They may be the same or different. Q 23 This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between the carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O-, and two Q 23 They may be the same or different. Q 24 Q 24 If the atom at Z to which the bond is formed is a carbon atom, then Q 22 Q 24 If the atom at Z to which it is bonded is a nitrogen atom, then Q 23 Q 1 Q 24 If you have 2 or more Q 24 They may be the same or different. Q 25 This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between the carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O-, Q 1 Q 25 If you have 2 or more Q 25 They may be the same or different. Q 26 This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between the carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O- Z is Q 14 It has a carbon or nitrogen atom that is directly bonded to it and Q 24 It is a group having an a1+b1 valence ring structure with a carbon or nitrogen atom to which it is directly bonded, R 1 Q is a hydrogen atom or an alkyl group, 1 R 1 If you have 2 or more of these, then 2 or more R1 They may be the same or different. R 2 is a hydrogen atom, a hydroxyl group, an alkyl group, or an acyloxy group. R 3 is an alkyl group, R 6 These are a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. d1 is an integer between 0 and 3, d2 is an integer between 0 and 3, and d1 + d2 is an integer between 1 and 3. d3 is an integer between 0 and 3, d4 is an integer between 0 and 3, and d3 + d4 is an integer between 1 and 3. d1+d3 is Q 1 In this case, it is an integer from 1 to 5. d2 + d4 is Q 1 In this case, it is an integer from 1 to 5. e1 + e2 is either 3 or 4. e1 is Q 1 In this case, it is an integer from 1 to 3. e2 is Q 1 In this case, it is an integer from 1 to 3. h1 is Q 1 In this case, it is an integer greater than or equal to 1. h2 is an integer greater than or equal to 1, i1 + i2 is either 3 or 4. i1 is Q 1 In this case, it is an integer from 1 to 3. i2 is Q 1 In this case, it is an integer from 1 to 3. i3 is either 2 or 3.

[0011] [5] A fluorine-containing ether compound of [1], which is represented by the following formula (1B). [T-] b2 Q 2 -Q f -Q 2 [-T] b2 (1B) however, Q f It has the first substructure and the second substructure, Furthermore, it is a divalent group having five or more of the first substructure or two or more of the second substructure, with both bond ends being carbon atoms. Q 2 This is a single bond or a b2+1 valent linking group, and has two Q 2 They may be the same or different. T is -R f6 -Ar, -OR 10 , -SR 10 , -NOR 10 -C(=O)R 10 , -N(R 10 )2, -N + (R 10 )3X 3 -C≡N, -C(=NR) 10 )-R 10 , -N + ≡N, -N=NR 10 , -C(=O)OR 10 -C(=O)OX 2 -C(=O)OX 4 -C(=O)OC(=O)R 10 , -SO2R 10 -SO3H, -SO3X 2 -OP(=O)(-OR 10 )2, -OP(=O)(-OR 10 )(-OX 2 ), -N=C=O, -Si(R) 3-c (L) c , -C(R 10 )=C(R 10 )2, -C≡C(R 10 ), -C(=O)N(R 10 )2, -N(R 10 )C(=O)R 10 , -Si(R 10 )2-O-Si(R 10 )3, -NH-C(=O)R 10 -C(=O)NHR 10 ,-I, [ka] R f6 These are fluoroalkyl groups having 1 to 6 carbon atoms. R 10R is a hydrogen atom, a C1-C6 alkyl group or fluoroalkyl group, or an aryl group which may have substituents. 10 If there are 2 or more, then 2 or more R 10 They may be the same or different from each other. Ar is an aryl group which may have substituents. X 2 These are alkali metal ions or ammonium ions, X 3 It is a halide ion, X 4 It is a halogen atom, R is an alkyl group, L is a hydrolyzable group or a hydroxyl group, and the two or more Ls in T may be the same or different. b2 is an integer greater than or equal to 1, and the two b2s may be the same or different. c is 2 or 3, If there are two or more T's, the two or more T's may be the same or different.

[0012] [6] Q f However, the group is represented by the following formula (g1b), which is the fluorine-containing ether compound of [5]. -R f4 -(OR f2 ) m (OR f3 ) n - (g1b) however, R f2 This is a fluoroalkylene group having 1 to 6 carbon atoms (however, Q 2 R that joins f2 Q 2 At least one fluorine atom is bonded to the carbon atom at the terminal end of the side. R f3 This refers to a divalent fluorinated hydrocarbon group having a fluorine-containing ring structure (however, Q 2 R that joins f3 Q 2 At least one fluorine atom is bonded to the carbon atom at the terminal end of the side. Rf4 This refers to a fluoroalkylene group having 1 to 6 carbon atoms, or a divalent fluorinated hydrocarbon group having a fluorine-containing ring structure (however, R f4 Q 2 At least one fluorine atom is bonded to the carbon atom at the terminal end of the side. n is R f4 If it has a fluorine-containing ring structure, it is an integer from 0 to 500, R f4 If it does not have a fluorine-containing ring structure, it is an integer from 1 to 500, and if n is 2 or greater, (OR f3 ) n is two or more ORs f3 It may consist of, When n is 0, m is an integer between 5 and 500. When n is 1 or greater, m is an integer between 2 and 500. If m is 2 or greater, (OR f2 ) m is two or more ORs f2 It may consist of, m pieces (OR f2 ) and n (OR f3 The order of joining the elements is not restricted.

[0013] [7] Q 2 A fluorine-containing ether compound of [5] or [6], wherein the group is represented by formula (g2-1) (where b2 = d2 + d4), formula (g2-2) (where b2 = e2), formula (g2-3) (where b2 = 2), formula (g2-4) (where b2 = h2), formula (g2-5) (where b2 = i2), formula (g2-6) (where b2 = 1), or formula (g2-7) (where b2 = i3). [ka] (-AQ 12 -) e1 C(R 2 ) 4-e1-e2 (-Q 22 -) e2 (g2-2) -AQ13 -N(-Q 23 -)2(g2-3) (-AQ 14 -) h1 Z(-Q 24 -) h2 (g2-4) (-AQ 15 -) i1 Si(R 3 ) 4-i1-i2 (-Q 25 -) i2 (g2-5) -AQ 26 - (g2-6) -AQ 12 -CH(-Q 22 -)-Si(R 3 ) 3-i3 (-Q 25 -) i3 (g2-7) however, In equations (g2-1) to (g2-7), side A is Q. f Connect to Q 22 Q 23 Q 24 Q 25 and Q 26 The side is connected to T, A is a single bond, -C(O)NR 6 -, -C(O)-, -OC(O)O-, -NHC(O)O-, -NHC(O)NR 6 -, -O- or -SO2NR 6 -and, Q 11 This refers to a single bond, -O-, an alkylene group, or an alkylene group with 2 or more carbon atoms with -C(O)NR between carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O- Q 12 This refers to a single bond, an alkylene group, or an alkylene group with 2 or more carbon atoms with -C(O)NR between carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O-, Q 2 Q 12 If you have 2 or more Q 12Q can be the same or different. 13 This refers to a single bond (where A is -C(O)-), an alkylene group, and an -C(O)NR between carbon atoms of an alkylene group with 2 or more carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O-, or a group having -C(O)- at the N-side terminal of an alkylene group, Q 14 Q 14 If the atom at Z to which the bond is formed is a carbon atom, then Q 12 Q 14 If the atom at Z to which it is bonded is a nitrogen atom, then Q 13 Q 2 Q 14 If you have 2 or more Q 14 They may be the same or different. Q 15 This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between the carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O-, Q 2 Q 15 If you have 2 or more Q 15 They may be the same or different. Q 22 This refers to alkylene groups, and alkylene groups with 2 or more carbon atoms, where the -C(O)NR is formed between the carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O-, or -C(O)NR at the non-T-connected end of the alkylene group. 6 -, -C(O)-, -NR 6 - or -O- groups, or alkylene groups having 2 or more carbon atoms with -C(O)NR between carbon atoms. 6 -, -C(O)-, -NR 6 - or -O- and -C(O)NR at the end that is not connected to T 6 -, -C(O)-, -NR 6 A group having - or -O-, Q 2 Q 22 If you have 2 or more Q 22 They may be the same or different. Q 23 This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between the carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O-, and two Q 23 They may be the same or different. Q 24 Q 24 If the atom at Z to which the bond is formed is a carbon atom, then Q 22 Q 24 If the atom at Z to which it is bonded is a nitrogen atom, then Q 23 Q 2 Q 24 If you have 2 or more Q 24 They may be the same or different. Q 25 This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between the carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O-, Q 2 Q 25 If you have 2 or more Q 25 They may be the same or different. Q 26 This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between the carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O- Z is Q 14 It has a carbon or nitrogen atom that is directly bonded to it and Q 24 It is a group having a b2+1 valent ring structure with a carbon or nitrogen atom to which it is directly bonded, R 1 Q is a hydrogen atom or an alkyl group, 2 R 1 If you have 2 or more of these, then 2 or more R 1 They may be the same or different. R 2 is a hydrogen atom, a hydroxyl group, an alkyl group, or an acyloxy group. R 3 is an alkyl group, R 6 These are a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. d1 is an integer between 0 and 3, d2 is an integer between 0 and 3, and d1 + d2 is an integer between 1 and 3. d3 is an integer between 0 and 3, d4 is an integer between 0 and 3, and d3 + d4 is an integer between 1 and 3. d1+d3 is Q 2 In this case, it is 1, d2 + d4 is Q 2 In this case, it is an integer between 3 and 5. e1 + e2 is either 3 or 4. e1 is Q 2 In this case, it is 1, e2 is Q 2 In this case, it is 2 or 3, h1 is Q 2 In this case, it is 1, h2 is an integer greater than or equal to 1, i1 + i2 is either 3 or 4. i1 is Q 2 In this case, it is 1, i2 is Q 2 In this case, it is 2 or 3, i3 is either 2 or 3.

[0014] [8] Any of the fluorine-containing ether compounds from [1] to [7], wherein the fluorine-containing ring structure is a four-membered ring. [9] A fluorine-containing ether compound of any of [1] to [8] having a number-average molecular weight of 2,500 or more.

[10] T is -Si(R) 3-c (L) c The fluorine-containing ether compound is one of the following [2] to [9]. however, R is an alkyl group, L is a hydrolyzable group or a hydroxyl group, and the two or more Ls in T may be the same or different. c is either 2 or 3.

[0015] A fluorine-containing ether composition characterized by containing one or more fluorine-containing ether compounds from [1] to

[10] and other fluorine-containing ether compounds. A coating liquid characterized by comprising any of the fluorine-containing ether compounds from [1] to

[10] or the fluorine-containing ether composition of

[11] and a liquid medium.

[13] An article characterized by having a surface layer formed from any of the fluorine-containing ether compounds [1] to

[10] or the fluorine-containing ether composition

[11] on the surface of a substrate.

[14] The article of

[13] having the surface layer on the surface of a component that constitutes the surface of a touch panel that is touched by a finger.

[15] A method for manufacturing an article, characterized by treating the surface of a substrate by a dry coating method using any of the fluorine-containing ether compounds from [1] to

[10] or the fluorine-containing ether composition of

[11] to form a surface layer formed from the fluorine-containing ether compound or the fluorine-containing ether composition on the surface of the substrate.

[16] A method for manufacturing an article, characterized by applying the coating liquid of

[12] to the surface of a substrate by a wet coating method and drying it to form a surface layer on the surface of the substrate that is made of the fluorine-containing ether compound or the fluorine-containing ether composition.

[0016]

[17] A fluorine-containing ether compound, which is represented by the following formula (2A). [R f -] a1 Q 10 [-CH=CH2] b1 (2A) however, R f This is a monovalent polyfluoropolyether chain having carbon atoms at its bonding ends, having at least one of a monovalent fluorine-containing ring structure at the free end and a divalent fluorine-containing ring structure in the main chain (where at least one fluorine atom is bonded to the carbon atoms at the bonding ends), and R f If you have 2 or more of these, then 2 or more R f They may be the same or different. Q 10This is a linked group with a1+b1 valency, a1 is an integer greater than or equal to 1. b1 is an integer greater than or equal to 1.

[18] A fluorine-containing ether compound, which is represented by the following formula (2B). [CH2=CH-] b2 Q 20 -Q f -Q 20 [-CH=CH2] b2 (2B) however, Q f This is a divalent polyfluoropolyether chain having a divalent fluorine-containing ring structure in the main chain, with both bond ends being carbon atoms (however, at least one fluorine atom is bonded to each carbon atom at both bond ends). Q 20 This is a b2+1 valent linking group, and has two Q 20 They may be the same or different. b2 is an integer greater than or equal to 1, and the two b2s may be the same or different.

[0017]

[19] A method for producing a fluorine-containing compound, characterized by reacting a compound represented by formula (11) below with a compound represented by formula (12) below to obtain a compound represented by formula (21) below. [ka] however, R 11 This refers to an alkylene group, an alkylene group having 2 or more carbon atoms with an -O- between the carbon atoms, a fluoroalkylene group (where E is -OH, the E-side terminal is CH2), or a fluoroalkylene group having 2 or more carbon atoms with an -O- between the carbon atoms (where E is -OH, the E-side terminal is CH2), R 12 This is a halogen atom, a perfluoroalkyl group, or a group having -O- between carbon atoms of a perfluoroalkyl group having 2 or more carbon atoms. q is either 0 or 1, E is -OH, -OR14 , -SR 14 , -C(O)OR 14 -C(O)NHR 14 -C(O)NR 14 R 15 -NH2, -NHR 14 , -NR 14 R 15 , -SO2X 1 , -C(O)X 1 , or a halogen atom, R 14 and R 15 These are each an alkyl group independently, X 1 It is a halogen atom.

[0018]

[20] A method for producing a fluorine-containing compound, characterized by reacting a compound represented by formula (11) with a compound represented by formula (13) to obtain a compound represented by formula (22). [ka] however, R 11 This refers to an alkylene group, an alkylene group having 2 or more carbon atoms with an -O- between the carbon atoms, a fluoroalkylene group (where E is -OH, the E-side terminal is CH2), or a fluoroalkylene group having 2 or more carbon atoms with an -O- between the carbon atoms (where E is -OH, the E-side terminal is CH2), R 13 This refers to a fluoroalkylene group, a group having -O- at both ends of a fluoroalkylene group, or a group having -O- between carbon atoms of a fluoroalkylene group having 2 or more carbon atoms. q is either 0 or 1, E is -OH, -OR 14 , -SR 14 , -C(O)OR 14 -C(O)NHR 14 -C(O)NR 14 R 15 -NH2, -NHR 14 , -NR 14 R 15 , -SO2X1 , -C(O)X 1 , or a halogen atom, R 14 and R 15 These are each an alkyl group independently, X 1 is a halogen atom, There are multiple R in equation (22) 11 q and E may be the same or different.

[0019]

[21] A method for producing a fluorine-containing compound, characterized by reacting compounds represented by the following formula (11) with each other to obtain a compound represented by the following formula (23). [ka] however, R 11 This refers to an alkylene group, an alkylene group having 2 or more carbon atoms with an -O- between the carbon atoms, a fluoroalkylene group (where E is -OH, the E-side terminal is CH2), or a fluoroalkylene group having 2 or more carbon atoms with an -O- between the carbon atoms (where E is -OH, the E-side terminal is CH2), q is either 0 or 1, E is -OH, -OR 14 , -SR 14 , -C(O)OR 14 -C(O)NHR 14 -C(O)NR 14 R 15 -NH2, -NHR 14 , -NR 14 R 15 , -SO2X 1 , -C(O)X 1 , or a halogen atom, R 14 and R 15 These are each an alkyl group independently, X 1 is a halogen atom, There are multiple R in equation (23) 11 q and E may be the same or different.

[0020]

[22] A method for producing a fluorine-containing compound, characterized by reacting compounds represented by the following formula (13) with each other to obtain a compound represented by the following formula (24). [ka] however, R 13 This refers to a fluoroalkylene group, a group having -O- at both ends of a fluoroalkylene group, or a group having -O- between carbon atoms of a fluoroalkylene group having 2 or more carbon atoms. r is an integer greater than or equal to 1, There are multiple R in equation (24) 13 They may be the same or different.

[0021]

[23] A method for producing a fluorine-containing compound, characterized by reacting a compound represented by formula (11) below with a compound represented by formula (13) below to obtain a compound represented by formula (25) below. [ka] however, R 11 This refers to an alkylene group, an alkylene group having 2 or more carbon atoms with an -O- between the carbon atoms, a fluoroalkylene group (where E is -OH, the E-side terminal is CH2), or a fluoroalkylene group having 2 or more carbon atoms with an -O- between the carbon atoms (where E is -OH, the E-side terminal is CH2), R 13 This refers to a fluoroalkylene group, a group having -O- at both ends of a fluoroalkylene group, or a group having -O- between carbon atoms of a fluoroalkylene group having 2 or more carbon atoms. q is either 0 or 1, r is an integer greater than or equal to 1, E is -OH, -OR 14 , -SR 14 , -C(O)OR 14 -C(O)NHR 14 -C(O)NR 14 R 15-NH2, -NHR 14 , -NR 14 R 15 , -SO2X 1 , -C(O)X 1 , or a halogen atom, R 14 and R 15 These are each an alkyl group independently, X 1 is a halogen atom, There are multiple R in equation (25) 13 They may be the same or different.

[0022]

[24] A method for producing a fluorine-containing compound, characterized by reacting compounds represented by the following formula (12) with each other to obtain a compound represented by the following formula (26). [ka] however, R 12 This is a halogen atom, a perfluoroalkyl group, or a group having -O- between carbon atoms of a perfluoroalkyl group having 2 or more carbon atoms, There are multiple R in equation (26) 12 They may be the same or different.

[0023]

[25] A method for producing a fluorine-containing compound, characterized by reacting a compound represented by formula (12) below with a compound represented by formula (13) below to obtain a compound represented by formula (27) below. [ka] however, R 12 This is a halogen atom, a perfluoroalkyl group, or a group having -O- between carbon atoms of a perfluoroalkyl group having 2 or more carbon atoms. R 13 This refers to a fluoroalkylene group, a group having -O- at both ends of a fluoroalkylene group, or a group having -O- between carbon atoms of a fluoroalkylene group having 2 or more carbon atoms. r2 is an integer greater than or equal to 1, There are multiple R in equation (27) 13 They may be the same or different. [Effects of the Invention]

[0024] The present invention provides a fluorine-containing ether compound with excellent chemical resistance, a fluorine-containing ether composition and coating liquid capable of forming a surface layer with excellent chemical resistance, an article having a surface layer with excellent chemical resistance and a method for producing the same, and a method for producing a fluorine-containing compound useful as a raw material for the fluorine-containing ether compound. [Modes for carrying out the invention]

[0025] In this specification, the compound represented by formula (1A) will be referred to as compound (1A). The same applies to compounds represented by other formulas. Furthermore, the group represented by formula (g1a) will be denoted as base (g1a). Other groups represented by other formulas will be denoted similarly. "Oxyfluoro(cyclo)alkylene" is a general term encompassing both oxyfluoroalkylene and oxyfluorocycloalkylene. The chemical formula for an oxyfluoro(cyclo)alkylene unit shall be written with the oxygen atom located to the left of the fluoro(cyclo)alkylene group.

[0026] The following terms used in this specification have the meanings set forth below. A "free end" in a polyfluoropolyether chain refers to the end that is not the side to which a reactive silyl group is attached via a linking group. The term "terminal region" refers to the area composed of oxyfluoro(cyclo)alkylene units, including the aforementioned "free end." A "fluorine-containing ring structure" is a group that includes a group in which at least some of the hydrogen atoms bonded to carbon atoms constituting an aliphatic or aromatic ring are substituted with fluorine atoms, and which may also contain heteroatoms such as oxygen atoms, nitrogen atoms, and sulfur atoms in the carbon chain. Examples of "fluorine-containing ring structures" include groups containing fluoroaryl groups, fluoroarylene groups, fluorocycloalkyl groups, and fluorocycloalkylene groups. A "free-end monovalent fluorine-containing ring structure" refers to a ring structure in which one of the carbon atoms constituting the fluorine-containing ring is a carbon atom at the end of the main chain of a polyfluoropolyether chain that is not bonded to a linking group, and thus refers to a fluorine-containing ring structure that constitutes the terminal region. Examples of "free-end monovalent fluorine-containing ring structures" include monovalent groups such as fluorocycloalkyl groups and fluoroaryl groups. A "divalent fluorine-containing ring structure in the middle of the main chain" means a ring structure in which one or more carbon atoms constituting the fluorine-containing ring are carbon atoms that make up the main chain of the polyfluoropolyether chain. Examples of "divalent fluorine-containing ring structures in the middle of the main chain" include divalent groups such as fluorocycloalkylene groups and fluoroarylene groups. A "fluorine-containing aliphatic ring structure" is a group in which at least some of the hydrogen atoms bonded to the carbon atoms constituting the aliphatic ring are replaced with fluorine atoms. The atoms constituting the fluorine-containing aliphatic ring may include oxygen atoms, nitrogen atoms, etc., in addition to carbon atoms, but it is preferable that it consists only of carbon atoms or of carbon atoms and oxygen atoms. Examples of "fluorine-containing aliphatic ring structures" include groups containing fluorocycloalkyl groups and fluorocycloalkylene groups.

[0027] "Reactive silyl groups" is a general term for hydrolyzable silyl groups and silanol groups (Si-OH). Reactive silyl groups include, for example, -Si(R) as described later. 3-c (L) c That is the case. A "hydrolyzable silyl group" refers to a group that can undergo hydrolysis to form a silanol group. The term "surface layer" refers to the layer formed on the surface of the substrate. Fluorine-containing ether compounds, polyfluoropolyether chains (R f Ya Q f If it is a mixture of multiple fluorine-containing ether compounds with different chain lengths, then the polyfluoropolyether chain (R f Ya Q f The "molecular weight" of ) is, 1 H-NMR and 19The number-average molecular weight is calculated by determining the number (average value) of oxyfluoro(cyclo)alkylene units relative to the terminal group using F-NMR. The terminal group is, for example, R in formula (g1a). f1 Or T in equation (1A) or equation (1B). Fluorine-containing ether compounds, polyfluoropolyether chains (R f Ya Q f If the chain length of the polyfluoropolyether chain (R) is that of a single fluorine-containing ether compound, then the polyfluoropolyether chain (R) f Ya Q f The "molecular weight" of ) is, 1 H-NMR and 19 R by F-NMR f This is the molecular weight calculated by determining the structure of the molecule.

[0028] [Fluorine-containing ether compounds] The fluorine-containing ether compound of the present invention (hereinafter also referred to as "the compound") is a compound having a polyfluoropolyether chain, wherein the polyfluoropolyether chain has a fluorine-containing ring structure. The fluorine-containing ring structure may have one or more heteroatoms. The presence of the specific fluorine-containing ring structure in the polyfluoropolyether chain results in a compound with excellent chemical resistance. In this compound, when the polyfluoropolyether chain has one fluorine-containing ring structure, the polyfluoropolyether chain has five or more oxyfluoroalkylene units. This imparts flexibility to the polyfluoropolyether chain and ensures a sufficient amount of fluorine to impart the various properties of a fluorine-containing ether compound. Furthermore, in this compound, if the polyfluoropolyether chain has two or more fluorine-containing ring structures, the polyfluoropolyether chain has two or more (preferably five or more) oxyfluoroalkylene units. This imparts flexibility to the polyfluoropolyether chain and ensures a sufficient amount of fluorine to impart the various properties of the fluorine-containing ether compound. The above fluorine-containing ring structure is the OR described later. f13 (This is the second substructure.) The oxyfluoroalkylene group is the OR, which will be discussed later.f12 This is the first substructure. As for the polyfluoropolyether chain, a perfluoropolyether chain is preferred because it exhibits excellent properties due to the imparting effect of fluorine. Furthermore, due to the excellent properties imparted by fluorine, the molecular weight of this compound is preferably 2,500 or more, more preferably 2,500 to 100,000, and even more preferably 3,000 to 10,000.

[0029] The compound preferably has a structure in which a polyfluoropolyether chain and a group that imparts various functions to the compound (T in formulas (1A) and (1B) described later (hereinafter also referred to as the functional imparting group T)) are linked directly or via a linking group.

[0030] The polyfluoropolyether chain in the present invention has a fluorine-containing ring structure which may have heteroatoms. In the case of a monovalent polyfluoropolyether chain, it has at least one of a monovalent fluorine-containing ring structure at the free end and a divalent fluorine-containing ring structure in the main chain. In the case of a divalent polyfluoropolyether chain, it has a divalent fluorine-containing ring structure in the main chain. The polyfluoropolyether chain has a fluorine-containing ring structure, resulting in excellent chemical resistance and various other durability properties, such as light resistance. As for the fluorine-containing ring structure, a 3- to 8-membered ring is preferred because it facilitates the production of this compound, a 4- to 6-membered ring is more preferred because it provides even better friction resistance and slip resistance to the surface layer, a 4- to 5-membered ring is even more preferred, and a 4-membered ring is particularly preferred.

[0031] This compound is a fluorine-containing ether compound having a first substructure represented by the following formula (1) (hereinafter also referred to as "substructure 1") and a second substructure represented by the following formula (2) (hereinafter also referred to as "substructure 2"). The system has five or more of the aforementioned substructure 1, or The present invention is characterized by having two or more of the aforementioned substructures 2. -OR f12 - (1) -ORf13 - (2) however, R f12 This is a fluoroalkylene group having 1 to 6 carbon atoms. R f13 This is a group having a fluorine-containing ring structure, which may contain heteroatoms. In this compound, having one substructure 2 and five or more substructures 1 is preferable in terms of having high fingerprint stain removal properties.

[0032] In substructure 1, R f12 Because the fluoroalkylene group has 1 to 6 carbon atoms, flexibility is imparted to the polyfluoropolyether chain, resulting in excellent abrasion resistance and fingerprint stain removal when a surface layer is formed. R f12 As for the fluoroalkylene group, a linear fluoroalkylene group is preferred because it provides even better abrasion resistance and fingerprint stain removal properties for the surface layer. R f12 As the fluoroalkylene group, a perfluoroalkylene group is preferred because it offers even better abrasion resistance and fingerprint stain removal properties for the surface layer. All R f12 The proportion of perfluoroalkylene groups is preferably 60 mol% or more, more preferably 80 mol% or more, and particularly preferably 100 mol%, from the viewpoint of further improving the abrasion resistance and fingerprint stain removal properties of the surface layer.

[0033] In substructure 2, R f13Groups having a fluorine-containing ring structure which may have heteroatoms include, for example, fluorocycloalkylene groups which may have heteroatoms and substituents. Examples of heteroatoms include oxygen atoms, nitrogen atoms, and sulfur atoms, with oxygen atoms being preferred. The number of members in the ring containing the heteroatoms is preferably 3 to 8 from the viewpoint of ease of producing the compound, more preferably 4 to 6, even more preferably 4 to 5, and particularly preferably 4 from the viewpoint of even better friction resistance and slip resistance of the surface layer. Furthermore, from the viewpoint of excellent chemical resistance, a fluorine-containing ring structure which does not have heteroatoms is preferred. Furthermore, a fluorine-containing aliphatic ring structure is preferred for the fluorine-containing ring structure. As a fluorocycloalkylene group having a divalent fluorine-containing aliphatic ring structure, a perfluorocycloalkylene group is preferred because it offers even better friction resistance and fingerprint stain removal properties for the surface layer. The fluorocycloalkylene group may have a substituent, for example, a fluoroalkylene group. The number of carbon atoms in the fluoroalkylene group is preferably 1 to 6, and more preferably 1 to 4. As the fluoroalkylene group, a perfluoroalkylene group is preferred.

[0034] Furthermore, the fluoroalkylene group, which is a substituent, may be bonded to the oxygen atom of formula (2) above. In this case, formula (2) above is represented by the following formula (2a). -OR f14 R f15 - (2a) however, R f14 This is a fluoroalkylene group having 1 to 6 carbon atoms. R f15 This is a fluorine-containing ring structure which may have heteroatoms. f14 R f15 is R f13 It represents. Furthermore, substructure 2 may be present in the terminal region of the polyfluoropolyether chain. In this case, the terminal region is represented by the following formula (2b). -OR f13 R f16 (2b) However, R f13 As mentioned above, Rf16 R is a hydrogen atom, a fluorine atom, or a fluoroalkyl group having 1 to 6 carbon atoms. Hereinafter, R f13 R f16 This is sometimes referred to as a monovalent fluorine-containing ring structure. Examples of monovalent fluorine-containing ring structures include the group shown in the following formula. * in the formula indicates a bond.

[0035] [ka]

[0036] Examples of divalent fluorine-containing ring structures include fluorocycloalkylene groups and groups having -O- between carbon atoms of the fluorocycloalkylene group. The number of carbon atoms in the fluorocycloalkylene group is preferably 3 to 8 from the standpoint of ease of producing the compound, more preferably 4 to 6, and particularly preferably 4, from the standpoint of even better friction resistance and slip resistance of the surface layer. Perfluorocycloalkylene groups are preferred over fluorocycloalkylene groups because they offer even better abrasion resistance and fingerprint stain removal properties for the surface layer. The fluorocycloalkylene groups may have substituents such as fluoroalkyl groups. Examples of divalent fluorine-containing ring structures include the group shown in the following formula. * in the formula indicates a bond.

[0037] [ka]

[0038] The molecular weight of the polyfluoropolyether chain is preferably 100 to 6000, more preferably 500 to 5000, and particularly preferably 1000 to 4000, from the viewpoint of achieving both fingerprint stain removal and slip resistance of the surface layer, as well as chemical resistance. If the molecular weight of the polyfluoropolyether chain is above the lower limit of the above range, the fingerprint stain removal performance of the surface layer is further improved. If the molecular weight of the polyfluoropolyether chain is below the upper limit of the above range, the slip resistance of the surface layer is further improved. The molecular weight of the polyfluoropolyether chain is preferably 1500 to 10000, more preferably 2000 to 8000, and particularly preferably 2500 to 6000, from the viewpoint of further superior abrasion resistance and fingerprint stain removal of the surface layer, as well as chemical resistance. If the molecular weight of the polyfluoropolyether chain is above the lower limit of the above range, the abrasion resistance and fingerprint stain removal of the surface layer are further superior. If the molecular weight of the polyfluoropolyether chain is below the upper limit of the above range, the abrasion resistance of the surface layer is further superior.

[0039] (Compound (1A) and Compound (1B)) Of the compounds, compounds (1A) and (1B) are preferred because they offer even better abrasion resistance and fingerprint stain removal properties for the surface layer. [R f -] a1 Q 1 [-T] b1 (1A) [T-] b2 Q 2 -Q f -Q 2 [-T] b2 (1B) However, R f It is a monovalent group having the aforementioned substructure 1 and the aforementioned substructure 2, and having 5 or more of the aforementioned substructure 1 or 2 or more of the aforementioned substructure 2, with a carbon atom at the bond end, R f If you have 2 or more of these, then 2 or more R f They may be the same or different. Q f This is a divalent group having the aforementioned substructure 1 and substructure 2, and having five or more substructures 1 or two or more substructures 2, with both bond ends being carbon atoms. In particular, compound (1B) is preferable in terms of having only one substructure 2 and five or more substructures 1, as this provides high fingerprint stain removal properties. In particular, the total molecular weight of substructure 1 is preferably 1000 to 10000, and especially preferably 2000 to 6000. Q 1 This is a single bond or a linked group with a1+b1 valency. Q 2This is a single bond or a b2+1 valent linking group, and has two Q 2 They may be the same or different. T is -R f6 -Ar, -OR 10 , -SR 10 , -NOR 10 -C(=O)R 10 , -N(R 10 )2, -N + (R 10 )3X 3 -C≡N, -C(=NR) 10 )-R 10 , -N + ≡N, -N=NR 10 , -C(=O)OR 10 -C(=O)OX 2 -C(=O)OX 4 -C(=O)OC(=O)R 10 , -SO2R 10 -SO3H, -SO3X 2 -OP(=O)(-OR 10 )2, -OP(=O)(-OR 10 )(-OX 2 ), -N=C=O, -Si(R) 3-c (L) c , -C(R 10 )=C(R 10 )2, -C≡C(R 10 ), -C(=O)N(R 10 )2, -N(R 10 )C(=O)R 10 , -Si(R 10 )2-O-Si(R 10 )3, -NH-C(=O)R 10 -C(=O)NHR 10 ,-I, [ka] R f6 These are fluoroalkyl groups having 1 to 6 carbon atoms. R 10 R is a hydrogen atom, a C1-C6 alkyl group or fluoroalkyl group which may have substituents, or an aryl group which may have substituents. 10If there are 2 or more, then 2 or more R 10 They may be the same or different from each other. Ar is an aryl group which may have substituents. X 2 These are alkali metal ions or ammonium ions, X 3 It is a halide ion, X 4 It is a halogen atom, R is an alkyl group, L is a hydrolyzable group or a hydroxyl group, and the two or more Ls in T may be the same or different. b2 is an integer greater than or equal to 1, and the two b2s may be the same or different. c is 2 or 3, If there are two or more T's, the two or more T's may be the same or different.

[0040] Compound (1A) has R at its terminal f It has R at the end. f Compound (1A) has excellent chemical resistance and excellent surface layer fingerprint stain removal properties. Compound (1B) has Q f It has. Q f Compound (1B) having the above characteristics exhibits excellent chemical resistance and superior removal of fingerprints from the surface layer. Compound (1A) and Compound (1B) have the above-mentioned specific functional group T at their terminals. Compounds (1A) and (1B) having the functional group T at their terminals are strongly chemically bonded to the substrate, thereby imparting various functions to the compound, such as excellent abrasion resistance of the surface layer. For a1, values ​​1 to 6 are preferred, 1 to 4 are more preferred, and 1 or 2 are particularly preferred, due to the ease of producing compound (1A), excellent chemical resistance, and even better abrasion resistance and fingerprint stain removal properties of the surface layer. For b1, values ​​of 1 to 6 are preferred, more preferably 1 to 5, even more preferably 1 to 4, and particularly preferred 2 to 4, due to the ease of producing compound (1A), excellent chemical resistance, and even better abrasion resistance and fingerprint stain removal properties of the surface layer. For b2, values ​​of 1 to 6 are preferred, more preferably 1 to 5, even more preferably 1 to 4, and particularly preferred 2 to 4, due to the ease of producing compound (1B), excellent chemical resistance, and even better abrasion resistance and fingerprint stain removal properties of the surface layer.

[0041] R f This is a monovalent polyfluoropolyether chain whose bond ends are carbon atoms. f In particular, monovalent perfluoropolyether chains are more preferred due to their superior chemical resistance, and even better abrasion resistance and fingerprint stain removal properties of the surface layer. Q f This is a divalent polyfluoropolyether chain with carbon atoms at both end bonds. f Divalent perfluoropolyether chains are more preferred due to their superior chemical resistance, as well as their even better abrasion resistance and fingerprint stain removal properties on the surface layer. R f and Q f The preferred molecular weight range is the same as the preferred molecular weight range for the polyfluoropolyether chain described above.

[0042] R f For example, group (g1a) can be cited. Group (g1a) has one or more fluorine-containing ring structures. R f1 -(OR f2 ) m (OR f3 ) n - (g1a) However, R f1 This is a fluoroalkyl group having 1 to 20 carbon atoms, or a monovalent fluorinated hydrocarbon group having a fluorine-containing ring structure. f2 This is a fluoroalkylene group having 1 to 6 carbon atoms (however, Q 1 R that joins f2 Q 1At least one fluorine atom is bonded to the carbon atom at the end of the side. f3 This refers to a divalent fluorinated hydrocarbon group having a fluorine-containing ring structure (however, Q 1 R that joins f3 Q 1 At least one fluorine atom is bonded to the carbon atom at the terminal end of the side. n is R f1 If it has a fluorine-containing ring structure, it is an integer from 0 to 500, R f1 If it does not have a fluorine-containing ring structure, it is an integer from 1 to 500, and if n is 2 or greater, (OR f3 ) n is two or more ORs f3 It may consist of the following: Also, when n is 0, m is an integer between 5 and 500, when n is 1 or greater, m is an integer between 2 and 500, and when m is 2 or greater, (OR f2 ) m is two or more ORs f2 It may consist of m (OR f2 ) and n (OR f3 The order of joining the elements is not restricted.

[0043] Q f Examples include groups having the group (g1b). The group (g1b) has one or more fluorine-containing ring structures. -R f4 -(OR f2 ) m (OR f3 ) n - (g1b) However, R f2 This is a fluoroalkylene group having 1 to 6 carbon atoms (however, Q 2 R that joins f2 Q 2 At least one fluorine atom is bonded to the carbon atom at the end of the side. f3 This refers to a divalent fluorinated hydrocarbon group having a fluorine-containing ring structure (however, Q 2 R that joins f3 Q 2 At least one fluorine atom is bonded to the carbon atom at the end of the side. f4This refers to a fluoroalkylene group having 1 to 6 carbon atoms, or a divalent fluorinated hydrocarbon group having a fluorine-containing ring structure (however, R f4 Q 2 At least one fluorine atom is bonded to the carbon atom at the terminal end of the side. n is R f4 If it has a fluorine-containing ring structure, it is an integer from 0 to 500, R f4 If it does not have a fluorine-containing ring structure, it is an integer from 1 to 500, and if n is 2 or greater, (OR f3 ) n is two or more ORs f3 It may consist of the following: Also, when n is 0, m is an integer between 5 and 500, when n is 1 or greater, m is an integer between 2 and 500, and when m is 2 or greater, (OR f2 ) m is two or more ORs f2 It may consist of m (OR f2 ) and n (OR f3 The order of joining the elements is not restricted. Furthermore Q f Of these, the group (g1b1) is particularly preferred. -R f4 -(OR f2 ) mm1 -(OR f3 )-(OR f2 ) mm2 - (g1b1) However, mm1 + mm2 = m and n = 1. For the base (g1b1), it is preferable in terms of abrasion resistance that (mm1 + 1) and (mm2) are approximately equal. Here, "approximately equal" means that the ratio of (mm1 + 1) / mm2 is 0.5 to 2, preferably 0.75 to 1.33.

[0044] R f1 If the fluoroalkyl group has 1 to 20 carbon atoms, it exhibits excellent chemical resistance, and even better abrasion resistance and fingerprint stain removal properties of the surface layer. f1 The number of carbon atoms in the fluoroalkyl group is preferably 1 to 6, more preferably 1 to 4, and particularly preferably 1 to 3, from the standpoint of excellent chemical resistance, and even better abrasion resistance and fingerprint stain removal of the surface layer. Rf1 As the fluoroalkyl group, a perfluoroalkyl group is preferred because it has excellent chemical resistance, and even better surface layer abrasion resistance and fingerprint stain removal properties. f1 Compound (1A), in which the parent molecule is a perfluoroalkyl group, has a CF3- terminus. Compound (1A), with a CF3- terminus, can form a surface layer with low surface energy, thus further improving the abrasion resistance and fingerprint stain removal properties of the surface layer. R f1 Examples of fluoroalkyl groups include CF3-, CF3CF2-, CF3CF2CF2-, CF3CF2CF2CF2-, CF3CF2CF2CF2CF2CF2-, CF3CF(CF3)-, and (CF3CF2)2CF-.

[0045] R f1 The number of carbon atoms in the monovalent fluorinated hydrocarbon group having a fluorine-containing ring structure is preferably 3 to 20, more preferably 4 to 8, and particularly preferably 4 to 6. If the number of carbon atoms in the fluorinated hydrocarbon group is within the above range, the chemical resistance is excellent, and the abrasion resistance and fingerprint stain removal properties of the surface layer are even better. R f1 As the fluorinated hydrocarbon group, fluorocycloalkyl groups are preferred because they offer excellent chemical resistance and even better slip resistance of the surface layer. R f1 As for the fluorinated hydrocarbon group, a fully fluorinated hydrocarbon group is preferred because it has excellent chemical resistance, and even better abrasion resistance and fingerprint stain removal properties of the surface layer. R f1 Examples of fluorinated hydrocarbon groups include the monovalent fluorine-containing ring structure exemplified in the above formula.

[0046] R f2 or R f4 If the fluoroalkylene group has 1 to 6 carbon atoms, it exhibits excellent chemical resistance, and the abrasion resistance and fingerprint stain removal properties of the surface layer are further enhanced. R f2 or R f4As for the fluoroalkylene group, a linear fluoroalkylene group is preferred because it has excellent chemical resistance, and even better abrasion resistance and fingerprint stain removal properties of the surface layer. R f2 or R f4 As the fluoroalkylene group, a perfluoroalkylene group is preferred because it has excellent chemical resistance, and even better abrasion resistance and fingerprint stain removal properties of the surface layer. All R f2 The proportion of perfluoroalkylene groups is preferably 60 mol% or more, more preferably 80 mol% or more, and particularly preferably 100 mol%, from the standpoint of excellent chemical resistance, and even better abrasion resistance and fingerprint stain removal of the surface layer.

[0047] R f3 or R f4 The number of carbon atoms in the divalent fluorinated hydrocarbon group having a fluorine-containing ring structure is preferably 3 to 20, more preferably 4 to 8, and particularly preferably 4 to 6. If the number of carbon atoms in the fluorinated hydrocarbon group is within the above range, the chemical resistance is excellent, and the abrasion resistance and fingerprint stain removal properties of the surface layer are even better. R f3 or R f4 As the fluorinated hydrocarbon group, a fluorocycloalkylene group is preferred because it has excellent chemical resistance and even better slip resistance of the surface layer. R f3 or R f4 As for the fluorinated hydrocarbon group, a fully fluorinated hydrocarbon group is preferred because it has excellent chemical resistance, and even better abrasion resistance and fingerprint stain removal properties of the surface layer. R f3 or R f4 Examples of fluorinated hydrocarbon groups include the divalent fluorine-containing ring structure exemplified in the above formula.

[0048] When sufficient slip resistance is required for the surface layer, m is preferably an integer between 1 and 30, more preferably an integer between 1 and 20, and particularly preferably an integer between 1 and 10. If m is less than or equal to the upper limit of the above range, the slip resistance of the surface layer is further improved. When sufficient abrasion resistance and fingerprint stain removal properties are required for the surface layer, m is preferably an integer between 2 and 200, more preferably an integer between 5 and 150, and particularly preferably an integer between 10 and 100. If m is greater than or equal to the lower limit of the range, the chemical resistance is excellent, and the abrasion resistance and fingerprint stain removal properties of the surface layer are even better. If m is less than or equal to the upper limit of the range, the abrasion resistance of the surface layer is even better. In other words, if the number average molecular weights of compound (1A) and compound (1B) are too large, the number of hydrolyzable silyl groups per unit molecular weight decreases, and the abrasion resistance of the surface layer decreases. When sufficient slip resistance is required for the surface layer, n is preferably an integer between 1 and 200, more preferably an integer between 1 and 150, and particularly preferably an integer between 1 and 100. If n is less than or equal to the upper limit of the above range, the chemical resistance is excellent and the slip resistance of the surface layer is even better.

[0049] Furthermore, due to its excellent chemical resistance and superior slip resistance of the surface layer, when n is 0, R f1 or R f4 It is preferable that it has a fluorine-containing ring structure. When n is 1, R f1 or R f4 When the fluorine-containing ring structure is absent, or when n is 0, m is preferably an integer between 5 and 30, more preferably an integer between 6 and 20, and particularly preferably an integer between 7 and 10, from the viewpoint of excellent chemical resistance and excellent slip resistance of the surface layer. When n is 1, R f1 or R f4 When the ring has a fluorine-containing structure, or when n is an integer of 2 or more, m is preferably an integer from 1 to 30, more preferably an integer from 2 to 20, and particularly preferably an integer from 3 to 10, in order to have excellent chemical resistance and excellent slip resistance of the surface layer.

[0050] Ure f2Examples of oxyfluoroalkylene units include OCHF, OCF2CHF, OCHFCF2, OCF2CH2, OCH2CF2, OCF2CF2CHF, OCHFCF2CF2, OCF2CF2CH2, OCH2CF2CF2, OCF2CF2CF2CH2, OCH2CF2CF2CF2, OCF2CF2CF2CF2CH2, OCH2CF2CF2CF2CF2, OCF2CF2CF2CF2CF2CH2, OCH2CF2CF2CF2CF2CF2, OCF2, OCF2CF2CF2CF2, OCF(CF3)CF2, OCF2CF2CF2CF2CF2, OCF(CF3)CF2, OCF2CF2CF2CF2CF2, and OCF2CF2CF2CF2CF2CF2CF2.

[0051] Ure f3 For example, the oxyfluorocycloalkylene unit shown in the following formula can be cited. * in the formula indicates a bond.

[0052] [ka]

[0053] (OR f2 ) m (OR f3 ) n In the case where two or more oxyfluoro(cyclo)alkylene units are present, the bonding order of each oxyfluoro(cyclo)alkylene unit is not limited. For example, if OCF2CF2 and OCF2CF2CF2CF2 are present, OCF2CF2 and OCF2CF2CF2CF2 may be arranged randomly, alternately, or in blocks. If OCF2 and OCF2CF2 are present, it is preferable that both are arranged randomly. The presence of two or more oxyfluoro(cyclo)alkylene units means that there are two or more oxyfluoro(cyclo)alkylene units with different numbers of carbon atoms, two or more oxyfluoro(cyclo)alkylene units with different numbers of hydrogen atoms, two or more oxyfluoro(cyclo)alkylene units with different positions of hydrogen atoms, and two or more oxyfluoro(cyclo)alkylene units with the same number of carbon atoms but different in the presence or absence of side chains or the type of side chains (number of side chains, number of carbon atoms in side chains, etc.). For the arrangement of two or more oxyfluoro(cyclo)alkylene units, for example, {(OCF2) m1 (OCF2CF2) m2 The structure represented by} represents a random arrangement of m1 (OCF2) and m2 (OCF2CF2). Also, (OCF2CF2-OCF2CF2CF2CF2) m5 The structure represented by this symbol indicates that m5 (OCF2CF2) and m5 (OCF2CF2CF2CF2) are arranged alternately.

[0054] (OR) when n is 0 f2 ) m (OR f3 ) n Preferably, it has at least a part of the following structure. {(OCF2) m1 (OCF2CF2) m2}, (OCF2CF2) m3 , (OCF2CF2CF2) m4 , (OCF2CF2-OCF2CF2CF2CF2) m5 , (OCF2CF2CF2CF2CF2) m6 (OCF2) m7 , (OCF2CF2CF2CF2CF2) m6 (OCF2CF2) m7 , (OCF2CF2CF2CF2CF2CF2) m6 (OCF2) m7 , (OCF2CF2CF2CF2CF2CF2) m6 (OCF2CF2) m7 , (OCF2CF2CF2CF2CF2-OCF2) m8 , (OCF2CF2CF2CF2CF2-OCF2CF2) m8 , (OCF2CF2CF2CF2CF2CF2-OCF2) m8 , (OCF2CF2CF2CF2CF2CF2-OCF2CF2 m8 , (OCF2-OCF2CF2CF2CF2CF2) m8 , (OCF2-OCF2CF2CF2CF2CF2CF2) m8 , (OCF2CF2-OCF2CF2CF2CF2CF2) m8 , (OCF2CF2-OCF2CF2CF2CF2CF2CF2) m8 , (OCF(CF3)CF2) m9 . However, m1, m2, m3, m4, m5, m6, m7, m8, and m9 are integers greater than or equal to 1. The upper limits of m1, m2, m3, m4, m5, m6, m7, m8, and m9 are adjusted to match the upper limit of m.

[0055] (OR) when n is 0 f2 ) m (OR f3 ) n The following are preferred in terms of ease of producing compound (1A) and compound (1B). {(OCF2) m1 (OCF2CF2) m2}OCF2, (OCF2CF2) m3 OCF2, (OCF2CF2CF2) m4 OCF2CF2, (OCF2CF2)2{(OCF2) m1 (OCF2CF2) m2}OCF2, (OCF2CF2-OCF2CF2CF2CF2) m5 OCF2CF2OCF2CF2CF2, (OCF2-OCF2CF2CF2CF2CF2) m8 OCF2OCF2CF2CF2CF2, (OCF2-OCF2CF2CF2CF2CF2CF2) m8 OCF2OCF2CF2CF2CF2CF2, (OCF2CF2-OCF2CF2CF2CF2CF2) m8 OCF2CF2OCF2CF2CF2CF2, (OCF2CF2-OCF2CF2CF2CF2CF2CF2) m8 OCF2CF2OCF2CF2CF2CF2CF2, (OCF(CF3)CF2) m9 OCF(CF3).

[0056] (OR) f2 ) m (OR f3 ) n Preferably, it has at least a part of the following structure. (OCF2CF2-OCF2CF2CF2CF2) m11 -O(c-C4F6)-(OCF2CF2CF2CF2-OCF2CF2) m12 , (OCF2CF2CF2CF2-O(c-C4F6)) m13 , (OCF2CF2-OCF2CF2CF2CF2CF2CF2) m14 -O(c-C4F6)-(OCF2CF2CF2CF2CF2CF2-OCF2CF2) m15 . However, c-C4F6 is a perfluoro-1,2-cyclobutylene group, and m11, m12, m13, m14, and m15 are integers greater than or equal to 1. The upper limits of m11, m12, m13, m14, and m15 are adjusted to match the upper limits of m and n.

[0057] (OR)f2 ) m (OR f3 ) n The following are preferred in terms of ease of producing compound (1A) and compound (1B). OCF2CF2CF2(OCF2CF2-OCF2CF2CF2CF2) m11 -O(c-C4F6)-(OCF2CF2CF2CF2-OCF2CF2) m12 OCF2CF2CF2, OCF2CF2(OCF2CF2CF2CF2-O(c-C4F6)) m13 OCF2CF2CF2, O(c-C4F6)(OCF2CF2CF2CF2-O(c-C4F6)) m13 OCF2CF2CF2, OCF2CF2CF2(OCF2CF2-OCF2CF2CF2CF2CF2CF2) m11 -O(c-C4F6)-(OCF2CF2CF2CF2CF2CF2-OCF2CF2) m12 OCF2CF2CF2.

[0058] Q 1 This is a single bond, or a linear or branched linking group with a1+b1 valency. Q 2 A linking group is a single bond or a linear or branched linking group with a b2+1 valency. A linking group is an organic group with two or more valencies. Q 1 Or Q 2 When it is a single bond, this compound has a polyfluoroalkylene chain (R f Or Q f It has a structure in which a functional group T is directly bonded to ). Q 1 When a1+b1 is 3 or more, it is preferable that it further has at least one branching point (hereinafter referred to as "branching point P") selected from the group consisting of C, N, Si, ring structures, and a1+b1 valent organopolysiloxane residues. 2 When b2+1 is 3 or more, it is preferable to have at least one branching point (hereinafter referred to as "branching point P'") selected from the group consisting of C, N, Si, ring structures, and b2+1 valent organopolysiloxane residues.

[0059] As for the ring structure, a type selected from the group consisting of a 3- to 8-membered aliphatic ring, a 3- to 8-membered aromatic ring, a 3- to 8-membered heteroring, and a fused ring consisting of two or more of these rings is preferred, given the ease of producing compounds (1A) and (1B), and the superior abrasion resistance, light resistance, and chemical resistance of the surface layer. The ring structure shown in the following formula is particularly preferred. The ring structure may have substituents such as halogen atoms, alkyl groups (which may contain etheric oxygen atoms between carbon atoms), cycloalkyl groups, alkenyl groups, allyl groups, alkoxy groups, and oxo groups (=O).

[0060] [ka]

[0061] Examples of a1+b1 valent organopolysiloxane residues or b2+1 valent organopolysiloxane residues include the following groups. However, R in the following formula 5 R is a hydrogen atom, an alkyl group, an alkoxy group, or a phenyl group. 5 The number of carbon atoms in the alkyl and alkoxy groups is preferably 1 to 10, and particularly preferably 1.

[0062] [ka]

[0063] Q 1 and Q 2 is -C(O)NR 6 -, -C(O)O-, -C(O)-, -O-, -NR 6 -, -S-, -OC(O)O-, -NHC(O)O-, -NHC(O)NR 6 -, -SO2NR 6 -, -Si(R 6 )2-, -OSi(R 6It may further have at least one bond selected from the group consisting of )2-, -Si(CH3)2-Ph-Si(CH3)2- and divalent organopolysiloxane residues (hereinafter referred to as "bond B"). However, R 6 R is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group, and Ph is a phenylene group. 6 The number of carbon atoms in the alkyl group is preferably 1 to 3, and particularly preferably 1 to 2, from the standpoint of facilitating the production of compound (1A) and compound (1B).

[0064] Examples of divalent organopolysiloxane residues include the group shown in the following formula. However, R in the following formula 7 R is a hydrogen atom, an alkyl group, an alkoxy group, or a phenyl group. 7 The number of carbon atoms in the alkyl and alkoxy groups is preferably 1 to 10, and particularly preferably 1.

[0065] [ka]

[0066] As for bond B, -C(O)NR is chosen because it facilitates the production of compounds (1A) and (1B). 6 -, -C(O)-, -NR 6 -C(O)NR is preferred because it provides even better light resistance and chemical resistance to the surface layer. 6 - or -C(O)- is particularly preferred.

[0067] Q 1 Examples include combinations of two or more divalent hydrocarbon groups and one or more branching points P, or combinations of two or more hydrocarbon groups, one or more branching points P, and one or more bonds B. Q 2 Examples include combinations of two or more divalent hydrocarbon groups and one or more branch points P', or combinations of two or more hydrocarbon groups, one or more branch points P', and one or more bonds B. Examples of divalent hydrocarbon groups include divalent aliphatic hydrocarbon groups (alkylene groups, cycloalkylene groups, etc.) and divalent aromatic hydrocarbon groups (phenylene groups, etc.). The number of carbon atoms in the divalent hydrocarbon group is preferably 1 to 10, more preferably 1 to 6, and particularly preferably 1 to 4.

[0068] Q of the above combination 1 As for ease of producing compound (1A), the groups (g2-1) (where a1=d1+d3 and b1=d2+d4), (g2-2) (where a1=e1 and b1=e2), (g2-3) (where a1=1 and b1=2), (g2-4) (where a1=h1 and b1=h2), (g2-5) (where a1=i1 and b1=i2), (g2-6) (where a1=1 and b1=1), and (g2-7) (where a1=1 and b1=i3) are preferred. Q of the above combination 2 In terms of ease of producing compound (1B), the groups (g2-1) (where b2 = d2 + d4), (g2-2) (where b2 = e2), (g2-3) (where b2 = 2), (g2-4) (where b2 = h2), (g2-5) (where b2 = i2), (g2-6) (where b2 = 1), and (g2-7) (where b2 = i3) are preferred.

[0069] [ka]

[0070] (-AQ 12 -) e1 C(R 2 ) 4-e1-e2 (-Q 22 -) e2 (g2-2) -AQ 13 -N(-Q 23 -)2(g2-3) (-AQ 14 -) h1 Z(-Q 24-) h2 (g2-4) (-AQ 15 -) i1 Si(R 3 ) 4-i1-i2 (-Q 25 -) i2 (g2-5) -AQ 26 - (g2-6) -AQ 12 -CH(-Q 22 -)-Si(R 3 ) 3-i3 (-Q 25 -) i3 (g2-7)

[0071] However, in equations (g2-1) to (g2-7), side A is R f Or Q f Connect to Q 22 Q 23 Q 24 Q 25 Or Q 26 The side connects to T. A is a single bond, -C(O)NR 6 -, -C(O)-, -OC(O)O-, -NHC(O)O-, -NHC(O)NR 6 -, -O- or -SO2NR 6 - is. Q 11 This refers to a single bond, -O-, an alkylene group, or an alkylene group with 2 or more carbon atoms with -C(O)NR between carbon atoms. 6 -, -C(O)-, -NR 6 It is a group having - or -O-. Q 12 This refers to a single bond, an alkylene group, or an alkylene group with 2 or more carbon atoms with -C(O)NR between carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O-, Q 1 Or Q 2 Q 12 If you have 2 or more Q 12 They may be the same or different. Q 13 This refers to a single bond (where A is -C(O)-), an alkylene group, and an -C(O)NR between carbon atoms of an alkylene group with 2 or more carbon atoms. 6-, -C(O)-, -NR 6 A group having - or -O-, or a group having -C(O)- at the N-side terminal of an alkylene group. Q 14 Q 14 If the atom at Z to which the bond is formed is a carbon atom, then Q 12 Q 14 If the atom at Z to which it is bonded is a nitrogen atom, then Q 13 Q 1 Or Q 2 Q 14 If you have 2 or more Q 14 They may be the same or different. Q 15 This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between the carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O-, Q 1 Or Q 2 Q 15 If you have 2 or more Q 15 They may be the same or different. Q 22 This refers to alkylene groups, and alkylene groups with 2 or more carbon atoms, where the -C(O)NR is formed between the carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O-, or -C(O)NR at the non-T-connected end of the alkylene group. 6 -, -C(O)-, -NR 6 - or -O- groups, or alkylene groups having 2 or more carbon atoms with -C(O)NR between carbon atoms. 6 -, -C(O)-, -NR 6 - or -O- and -C(O)NR at the end that is not connected to T 6 -, -C(O)-, -NR 6 A group having - or -O-, Q 1 Or Q 2 Q 22 If you have 2 or more Q 22 They may be the same or different. Q 23 This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between the carbon atoms. 6 -, -C(O)-, -NR6 A group having - or -O-, and two Q 23 They may be the same or different. Q 24 Q 24 If the atom at Z to which the bond is formed is a carbon atom, then Q 22 Q 24 If the atom at Z to which it is bonded is a nitrogen atom, then Q 23 Q 1 Or Q 2 Q 24 If you have 2 or more Q 24 They may be the same or different. Q 25 This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between the carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O-, Q 1 Or Q 2 Q 25 If you have 2 or more Q 25 They may be the same or different. Q 26 This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between the carbon atoms. 6 -, -C(O)-, -NR 6 It is a group having - or -O-. Z is Q 14 It has a carbon or nitrogen atom that is directly bonded to it and Q 24 It is a group having a ring structure with a1+b1 or b2+1 valency, with a carbon or nitrogen atom directly bonded to it. 1 Q is a hydrogen atom or an alkyl group, 1 Or Q 2 R 1 If you have 2 or more of these, then 2 or more R 1 They may be the same or different. 2 R is a hydrogen atom, a hydroxyl group, an alkyl group, or an acyloxy group. 3 R is an alkyl group. 6 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. d1 is an integer from 0 to 3, preferably 1 or 2. d2 is an integer between 0 and 3, preferably 1 or 2. d1 + d2 is an integer between 1 and 3. d3 is an integer between 0 and 3, preferably 0 or 1. d4 is an integer between 0 and 3, preferably 2 or 3. d3 + d4 is an integer between 1 and 3. d1 + d3 is Q 1 In this case, it is an integer from 1 to 5, preferably 1 or 2, Q 2 In this case, it is 1. d2+d4 is Q 1 In this case, it is an integer from 1 to 5, preferably 4 or 5, Q 2 In this case, it is an integer between 3 and 5, with 4 or 5 being preferred. e1 + e2 is 3 or 4. e1 is Q 1 In this case, it is an integer from 1 to 3, preferably 1 or 2, Q 2 In this case, it is 1. e2 is Q 1 In this case, it is an integer from 1 to 3, preferably 2 or 3, Q 2 In this case, it is 2 or 3. h1 is Q 1 In this case, it is an integer of 1 or more, preferably 1 or 2, Q 2 In this case, it is 1. h2 is an integer greater than or equal to 1, preferably 2 or 3. i1 + i2 is 3 or 4. i1 is Q 1 In this case, it is an integer from 1 to 3, preferably 1 or 2, Q 2 In this case, it is 1. i2 is Q 1 In this case, it is an integer from 1 to 3, preferably 2 or 3, Q 2 In this case, it is 2 or 3. i3 is 2 or 3.

[0072] Q 11 Q 12 Q 13 Q 14 Q 15 Q 22 Q 23 Q 24 Q 25 and Q 26The number of carbon atoms in the alkylene group is preferably 1 to 10, more preferably 1 to 6, and particularly preferably 1 to 4, from the viewpoints of ease of producing the compound (1A) and the compound (1B), and further excellent antifriction property, light resistance and chemical resistance of the surface layer. However, the lower limit of the number of carbon atoms in the alkylene group when having a specific bond between carbon-carbon atoms is 2.

[0073] Examples of the ring structure in Z include the ring structures described above, and the preferred forms are the same. In addition, in the ring structure in Z, Q 14 or Q 24 is directly bonded, so for example, an alkylene group is not linked to the ring structure and Q 14 or Q 24 is not linked to the alkylene group.

[0074] R 1 、R [[ID=2(1)]] 2 and R 3 The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 to 2, from the viewpoint of ease of producing the compound (1A) and the compound (1B). R 2 The number of carbon atoms in the alkyl group portion of the acyloxy group is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 to 2, from the viewpoint of ease of producing the compound 1. h1 is preferably 1 to 6, more preferably 1 to 4, still more preferably 1 or 2, and particularly preferably 1, from the viewpoints of ease of producing the compound (1A) and the compound (1B), and further excellent antifriction property and fingerprint stain removability of the surface layer. h2 is preferably 2 to 6, more preferably, 2 to 4, and particularly preferably 2 or 3, from the viewpoints of ease of producing the compound (1A) and the compound (1B), and further excellent antifriction property and fingerprint stain removability of the surface layer.

[0075] Q 1Other forms include group (g2-8) (where a1 is the sum of d1 + d3 and b1 is k), group (g2-9) (where a1 is e1 and b1 is e2), group (g2-10) (where a1 is 1 and b1 is the sum of k), group (g2-11) (where a1 is h1 and b1 is the sum of k), group (g2-12) (where a1 is i1 and b1 is the sum of k), group (g2-13) (where a1 is 1 and b1 is k), and group (g2-14) (where a1 is 1 and b1 is the sum of k). Q 2 Other forms include group (g2-8) (where b2 is the sum of k), group (g2-9) (where b2 is e2), group (g2-10) (where b2 is the sum of k), group (g2-11) (where b2 is the sum of k), group (g2-12) (where b2 is the sum of k), group (g2-13) (where b2 is k), and group (g2-14) (where b2 is the sum of k).

[0076]

Chemical Formula

[0077] (-A-Q 12 -) e1 C(R 2 ) 4-e1-e2 (-Q 22 -G) e2 (g2-9) -A-Q 13 -N(-Q 23 -G)2(g2-10) (-A-Q 14 -) h1 Z(-Q 24 -G) h2 (g2-11) (-A-Q 15 -) i1 Si(R 3 ) 4-i1-i2 (-Q 25 -G) i2 (g2-12) -A-Q 26 -G (g2-13) -AQ 12 -CH(-Q 22 -G)-Si(R 3 ) 3-i3 (-Q 25 -G) i3 (g2-14)

[0078] However, in equations (g2-8) to (g2-14), side A is R f Or Q f It connects to and G connects to T. G is the base (g3) and Q 1 Or Q 2 The two or more Gs present in the expression may be the same or different. The signs of the elements other than G are the same as the signs in equations (g2-1) to (g2-7). -Si(R 8 ) 3-k (-Q 3 -) k (g3) However, in equation (g3), the Si side is Q. 22 Q 23 Q 24 Q 25 Or Q 26 Connect to Q 3 The side connects to T. 8 Q is an alkyl group. 3 This refers to alkylene groups, and alkylene groups with 2 or more carbon atoms, where the -C(O)NR is formed between the carbon atoms. 6 -, -C(O)-, -NR 6 - or a group having -O- or -(OSi(R 9 )2) p -O- and Q is 2 or greater. 3 They may be the same or different. k is 2 or 3. R 6 R is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. 9 is an alkyl group, a phenyl group, or an alkoxy group, and has two R 9 They may be the same or different. p is an integer from 0 to 5, and if p is 2 or greater, then (OSi(R) is 2 or greater. 9 )2) may be the same or different.

[0079] Q3 The number of carbon atoms in the alkylene group is preferably 1 to 10, more preferably 1 to 6, and particularly preferably 1 to 4, from the standpoint of facilitating the production of compounds (1A) and (1B), and further improving the abrasion resistance, light resistance, and chemical resistance of the surface layer. However, the lower limit of the number of carbon atoms in the alkylene group when there is a specific bond between carbon atoms is 2. R 8 The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 to 2, from the standpoint of facilitating the production of compound (1A) and compound (1B). R 9 The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 to 2, from the standpoint of facilitating the production of compound (1A) and compound (1B). R 9 The number of carbon atoms in the alkoxy group is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 to 2, from the viewpoint of excellent storage stability of compound (1A) and compound (1B). p is preferably 0 or 1.

[0080] T is a functional group that imparts various functions to this compound. These functions include, for example, improving adhesion to the substrate surface, imparting photocurability or thermocurability to the compound, imparting acidity or alkalinity to the compound, adjusting the solubility of the compound in specific solvents, and acting as a reactive group when synthesizing other compounds using this compound as a raw material. R f6 and R 10 The fluoroalkyl group in T preferably has 1 to 6 carbon atoms. The fluoroalkyl group may have other substituents. Compounds having a fluoroalkyl group as T have a high fluorine content and exhibit excellent properties such as low refractive index, low dielectric constant, water and oil repellency, heat resistance, chemical resistance, chemical stability, and transparency. Substituents that the fluoroalkyl group may have include fluorine atoms, halogen atoms such as chlorine atoms, alkyl groups having 1 to 6 carbon atoms, and those similar to those exemplified as the functionalizing group T. Ar and R 10The aryl group in this formula includes phenyl groups, naphthyl groups, and others, and may have substituents. Substituents that the aryl group may have include fluorine atoms, halogen atoms such as chlorine atoms, C1-C6 alkyl groups, and those similar to those exemplified as functionality-granting groups T. R 10 The alkyl group in is preferably one to six carbon atoms. The alkyl group may have other substituents. Examples of substituents that the alkyl group may have include halogen atoms such as chlorine atoms, alkyl groups having one to six carbon atoms, and those similar to those exemplified as the functional group T.

[0081] This compound, having a hydroxyl group, N-hydroxyl group, aldehyde group, ketone group, amino group, quaternary ammonium group, nitrile group, imino group, diazo group, carboxyl group, carboxylate, acid anhydride group, sulfo group, sulfonate, phosphate group, or phosphate as T, is endowed with various properties such as acidity, alkalinity, and hydrophilicity by the functional-imparting group T. For example, it can impart functions such as improved solubility in a specific solvent or improved adhesion to a specific substrate. Examples of counterions for quaternary ammonium salts include halide ions. Examples of counterions for carboxylates, sulfonates, and phosphates include alkali metal ions and ammonium ions. Groups having a carbon-carbon double bond include vinyl groups, acryloyloxy groups, methacryloyloxy groups, and olefins. By combining this compound having a carbon-carbon double bond with a photoinitiator, a photocurable composition can be prepared, and the cured coating film obtained from this composition possesses both water-repellent and oil-repellent properties as well as hard-coat properties. Furthermore, this compound, which has an isocyanate group, epoxy group, glycidyl group, oxetanyl group, and mercapto group, can be combined with an epoxy curing agent to prepare a thermosetting or photocurable composition, and the cured coating obtained from this composition possesses both water-repellent and oil-repellent properties as well as hard coat properties. The amide, ester, ether, thioether, siloxane, and urea bonds in T are bonds that connect alkyl groups, fluoroalkyl groups, aryl groups, heteroaryl groups, etc., contained in T. These bonds may also provide other functional groups.

[0082] As the functionalizing group T of this compound, a hydroxyl group, an amino group, or a group having a carbon-carbon double bond is preferred from the viewpoint of synthesis, chemical stability, and adhesion to the substrate. Among the groups having a carbon-carbon double bond, an acryloyl group, a methacryloyl group, a vinyl group, an allyl group, or an olefin is preferred.

[0083] Furthermore, when this compound is used as a surface treatment agent to form a surface layer with excellent durability such as abrasion resistance, T is preferably a group having a reactive silyl group. A group having a reactive silyl group is -Si(R) 3-c (L) c This is preferable. However, a1 is an integer of 1 or more, b1 is an integer of 1 or more, R is an alkyl group, L is a hydrolyzable group or a hydroxyl group, the two or more Ls in T may be the same or different, and c is 2 or 3. The number of carbon atoms in the alkyl group of R is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 to 2, from the standpoint of facilitating the production of compounds (1A) and (1B). Examples of hydrolyzable groups of L include those similar to those described above, and the preferred form is also the same. Option c is particularly preferred because it results in stronger adhesion between the surface layer and the substrate. The multiple T groups in compound (1A) and compound (1B) may be the same or different. It is preferable that they be the same group from the standpoint of facilitating the production of compound (1A) and compound (1B).

[0084] The following structure is a concrete example of T. However, R in the formula a R represents an alkyl group, fluoroalkyl group, or aryl group which may have substituents. brepresents an optionally substituted fluoroalkyl group or an aryl group, and * represents a bond.

[0085]

Chemical formula

[0086] Examples of the compound (1A) and the compound (1B) include compounds represented by the following formula. The compounds represented by the following formula are easy to manufacture industrially, easy to handle, and have further excellent water and oil repellency, abrasion resistance, fingerprint stain removal property, lubricity, chemical resistance, light resistance and chemical resistance of the surface layer, and are particularly preferable in terms of particularly excellent light resistance. R in the compound represented by the following formula f , Q f and T are the same as R in the above-mentioned formula (1A) f or Q in the formula 2A f and the preferred forms are also the same.

[0087] Q 1 Examples of the compound (1A) in which is the group (g2-1) include compounds represented by the following formula.

[0088]

Chemical formula

[0089] Q 1 Examples of the compound (1A) in which is the group (g2-2) include compounds represented by the following formula.

[0090]

Chemical formula

[0091] Q 1 Examples of the compound (1A) in which is the group (g2-3) include compounds represented by the following formula.

[0092]

Chemical formula

[0093] Q 1 Examples of compounds (1A) in which (g2-4) is the group include the following compound.

[0094] [ka]

[0095] Q 1 Examples of compounds (1A) in which (g2-5) is the base are the compounds shown in the following formula.

[0096] [ka]

[0097] Q 1 Examples of compounds (1A) in which (g2-6) is the base are the compounds shown in the following formula.

[0098] [ka]

[0099] Q 1 Examples of compounds (1A) in which (g2-7) is the base are the compounds shown in the following formula.

[0100] [ka]

[0101] Q 1 Examples of compounds (1A) in which (g2-8) is the group include the following compound.

[0102] [ka]

[0103] Q 1Examples of compounds (1A) in which (g2-9) is the base are the compounds shown in the following formula.

[0104] [ka]

[0105] Q 1 Examples of compounds (1A) in which (g2-10) is the group (g2-10) include the compound shown in the following formula.

[0106] [ka]

[0107] Q 1 Examples of compounds (1A) in which (g2-11) is the group include the following compound.

[0108] [ka]

[0109] Q 1 Examples of compounds (1A) in which (g2-12) is the base (g2-12) include the compounds shown in the following formula.

[0110] [ka]

[0111] Q 1 Examples of compounds (1A) in which (g2-13) is the group include the following compound.

[0112] [ka]

[0113] Q 1 Examples of compounds (1A) in which (g2-14) is the base (g2-14) include the compound shown in the following formula.

[0114] [ka]

[0115] Q 2 Examples of compounds (1B) in which (g2-1) is the base (g2-1) include the compound shown in the following formula.

[0116] [ka]

[0117] Q 2 Examples of compounds (1B) in which the group (g2-2) is shown include the following compound.

[0118] [ka]

[0119] Q 2 Examples of compounds (1B) in which (g2-3) is the group include the compound shown in the following formula.

[0120] [ka]

[0121] Q 2 Examples of compounds (1B) in which (g2-4) is the base are the compounds shown in the following formula.

[0122] [ka]

[0123] Q 2 Examples of compounds (1B) in which (g2-5) is the base are the compounds shown in the following formula.

[0124] [ka]

[0125] Q 2 Examples of compounds (1B) in which (g2-6) is the base are the compounds shown in the following formula.

[0126] [ka]

[0127] Q 2 Examples of compounds (1B) in which (g2-7) is the base are the compounds shown in the following formula.

[0128] [ka]

[0129] Q 2 Examples of compounds (1B) in which (g2-9) is the base are the compounds shown in the following formula.

[0130] [ka]

[0131] One embodiment of the present invention is one in which T is -Si(R) 3-c (L) c This compound (hereinafter also referred to as the compound having a reactive silyl group) can form a surface layer with excellent fingerprint stain removal properties, abrasion resistance, and slip resistance. This compound, which has a reactive silyl group, comprises a polyfluoropolyether chain, a reactive silyl group, and a specific linking group that connects the polyfluoropolyether chain and the reactive silyl group. The polyfluoropolyether chain is preferably monovalent or divalent. That is, the compound may have the structure of "monovalent polyfluoropolyether chain-linking group-reactive silyl group," or it may have the structure of "reactive silyl group-linking group-divalent polyfluoropolyether chain-linking group-reactive silyl group."

[0132] This compound, which has a reactive silyl group, also has a polyfluoropolyether chain. This compound, which has a polyfluoropolyether chain, exhibits excellent fingerprint stain removal properties on surface layers. This compound, which has a reactive silyl group, has a reactive silyl group at at least one end. Because this compound, which has a reactive silyl group at the end, strongly chemically bonds with the substrate, the surface layer has excellent abrasion resistance. Furthermore, among the compounds having a reactive silyl group, compounds having a reactive silyl group at only one end are preferred. Compounds having a reactive silyl group at only one end are less prone to aggregation, resulting in an excellent appearance of the surface layer. They also exhibit excellent abrasion resistance and fingerprint stain removal properties of the surface layer.

[0133] A reactive silyl group is a group in which either a hydrolyzable group or a hydroxyl group, or both, are bonded to a silicon atom. A hydrolyzable group is a group that becomes a hydroxyl group through hydrolysis. Specifically, a hydrolyzable silyl group becomes a silanol group (Si-OH) through hydrolysis. The silanol group then undergoes further dehydration condensation reactions with other molecules to form a Si-O-Si bond. Additionally, the silanol group undergoes dehydration condensation reactions with hydroxyl groups on the surface of the substrate (substrate-OH) to form a chemical bond (substrate-O-Si). Examples of hydrolyzable groups include alkoxy groups, halogen atoms, acyl groups, and isocyanate groups. Among alkoxy groups, those having 1 to 6 carbon atoms are preferred. A chlorine atom is preferred as the halogen atom. As the hydrolyzable group, an alkoxy group or a halogen atom is preferred because it facilitates the production of this compound. As the hydrolyzable group, an alkoxy group having 1 to 4 carbon atoms is preferred because it produces less outgassing during coating and has excellent storage stability for this compound. An ethoxy group is particularly preferred when long-term storage stability of this compound is required, and a methoxy group is particularly preferred when the reaction time after coating is to be short.

[0134] The structure of this compound having a reactive silyl group, other than T, is the same as that described for the above compound, and the preferred structure is also the same. The following are specific examples of this compound having a reactive silyl group.

[0135] Q 1 Examples of compounds (1A) in which (g2-1) is the base (g2-1) include the following compound.

[0136] [ka]

[0137] Q 1 Examples of compounds (1A) in which the group (g2-2) is shown include the following compound.

[0138] [ka]

[0139] Q 1 Examples of compounds (1A) in which (g2-3) is the group include the following compound.

[0140] [ka]

[0141] Q 1 Examples of compounds (1A) in which (g2-4) is the group include the following compound.

[0142] [ka]

[0143] Q 1 Examples of compounds (1A) in which (g2-5) is the base are the compounds shown in the following formula.

[0144] [ka]

[0145] Q 1 Examples of compounds (1A) in which (g2-6) is the base are the compounds shown in the following formula.

[0146] [ka]

[0147] Q 1 Examples of compounds (1A) in which (g2-7) is the base are the compounds shown in the following formula.

[0148] [ka]

[0149] Q 1 Examples of compounds (1A) in which (g2-8) is the group include the following compound.

[0150] [ka]

[0151] Q 1 Examples of compounds (1A) in which (g2-9) is the base are the compounds shown in the following formula.

[0152] [ka]

[0153] Q 1 Examples of compounds (1A) in which (g2-10) is the group (g2-10) include the compound shown in the following formula.

[0154] [ka]

[0155] Q 1 Examples of compounds (1A) in which (g2-11) is the group include the following compound.

[0156] [ka]

[0157] Q 1 Examples of compounds (1A) in which (g2-12) is the base (g2-12) include the compounds shown in the following formula.

[0158] [ka]

[0159] Q 1 Examples of compounds (1A) in which (g2-13) is the group include the following compound.

[0160] [ka]

[0161] Q 1 Examples of compounds (1A) in which (g2-14) is the base (g2-14) include the compound shown in the following formula.

[0162] [ka]

[0163] Q 2 Examples of compounds (1B) in which (g2-1) is the base (g2-1) include the compound shown in the following formula.

[0164] [ka]

[0165] Q 2Examples of compounds (1B) in which the group (g2-2) is shown include the following compound.

[0166] [ka]

[0167] Q 2 Examples of compounds (1B) in which (g2-3) is the group include the compound shown in the following formula.

[0168] [ka]

[0169] Q 2 Examples of compounds (1B) in which (g2-4) is the base are the compounds shown in the following formula.

[0170] [ka]

[0171] Q 2 Examples of compounds (1B) in which (g2-5) is the base are the compounds shown in the following formula.

[0172] [ka]

[0173] Q 2 Examples of compounds (1B) in which (g2-6) is the base are the compounds shown in the following formula.

[0174] [ka]

[0175] Q 2 Examples of compounds (1B) in which (g2-7) is the base are the compounds shown in the following formula.

[0176] [ka]

[0177] Q 2 Examples of compounds (1B) in which (g2-9) is the base are the compounds shown in the following formula.

[0178] [ka]

[0179] Specific examples of this compound include the following compounds. However, n1 to n12 represent the number of repeating units and are adjusted as appropriate within the range of 1 to 200.

[0180] [ka]

[0181] (Method for producing compound (1A) and compound (1B)) Below, as an example of a method for producing compound (1A) and compound (1B), a method for producing compound (1A) and compound (1B) having a reactive silyl group will be described. When introducing a functional group T other than a reactive silyl group, in the production method described below, the desired functional group and a compound having a substituent capable of addition to a double bond may be used instead of compound (3a). Furthermore, although the reaction described below is an addition reaction to a double bond, the functional group T may also be introduced using known reactions such as esterification or amidation.

[0182] Compound (1A) can be produced, for example, by hydrosilylation of compound (2A) with compound (3a) or compound (3b). Compound (1B) can be produced, for example, by hydrosilylation of compound (2B) with compound (3a) or compound (3b). [R f -] a1 Q 10 [-CH=CH2] b1(2A) [CH2=CH-] b2 Q 20 -Q f -Q 20 [-CH=CH2] b2 (2B) However, in equation (2A), Q 10 is a linked group with a1+b1 valence, Q 10 The signs other than are the same as the signs in equation (1A). In equation (2B), Q 20 This is a b2+1 valent linking group, and has two Q 20 Q can be the same or different, 20 The signs other than those shown are the same as the signs in equation (1B). Q 10 [-CH=CH2] b1 Q in compound (1A) after hydrosilylation. 1 This is the result. Q 10 Q 1 Similar groups can be cited, and the preferred forms are also similar. Q 20 [-CH=CH2] b2 Q in compound (1B) after hydrosilylation. 2 This is the result. Q 20 Q 2 Similar groups can be cited, and the preferred forms are also similar.

[0183] HSi(R) 3-c (L) c (3a) HSi(R 8 ) 3-k [-(OSi(R 9 )2) p -O-Si(R) 3-c (L) c ] k (3b) However, the symbols in formulas (3a) and (3b) are the same as the symbols in formulas (1A), (1B), and (g3). Compound (3b) can be produced, for example, by the method described in the specification of Japanese Patent Application No. 2018-085493.

[0184] Q 10 [-CH=CH2] b1As for ease of producing compound (1A), the following groups are preferred: group (g4-1) (where a1=d1+d3 and b1=d2+d4), group (g4-2) (where a1=e1 and b1=e2), group (g4-3) (where a1=1 and b1=2), group (g4-4) (where a1=h1 and b1=h2), group (g4-5) (where a1=i1 and b1=i2), group (g4-6) (where a1=1 and b1=1), or group (g4-7) (where a1=1 and b1=i3). Q 20 [-CH=CH2] b2 In terms of ease of producing compound (1B), the groups (g4-1) (where b2 = d2 + d4), (g4-2) (where b2 = e2), (g4-3) (where b2 = 2), (g4-4) (where b2 = h2), (g4-5) (where b2 = i2), (g4-6) (where b2 = 1), and (g4-7) (where b2 = i3) are preferred.

[0185] [ka]

[0186] (-AQ 12 -) e1 C(R 2 ) 4-e1-e2 (-Q 220 -CH=CH2) e2 (g4-2) -AQ 13 -N(-Q 230 -CH=CH2)2(g4-3) (-AQ 14 -) h1 Z(-Q 240 -CH=CH2) h2 (g4-4) (-AQ 15 -) i1 Si(R 3 ) 4-i1-i2 (-Q 250 -CH=CH2) i2 (g4-5) -AQ 260 -CH=CH2(g4-6) -AQ 12 -CH(-Q 220 -CH=CH2)-Si(R 3 ) 3-i3 (-Q 250 -CH=CH2) i3 (g4-7)

[0187] However, Q 220 This refers to alkylene groups, and alkylene groups with 2 or more carbon atoms, where the -C(O)NR is formed between the carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O-, or -C(O)NR at the terminal end of the alkylene group that is not connected to -CH=CH2. 6 -, -C(O)-, -NR 6 - or -O- groups, or alkylene groups having 2 or more carbon atoms with -C(O)NR between carbon atoms. 6 -, -C(O)-, -NR 6 - or -O- and -C(O)NR at the end that is not connected to -CH=CH2 6 -, -C(O)-, -NR 6 A group having - or -O-, Q 10 Or Q 20 Q 220 If you have 2 or more Q 220 They may be the same or different. Q 230 This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between the carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O-, and two or more Q 230 They may be the same or different. Q 240 Q 240 If the atom at Z to which the bond is formed is a carbon atom, then Q 220 Q 240 If the atom at Z to which it is bonded is a nitrogen atom, then Q 230 Q 10 Or Q 20 Q 240 If you have 2 or more Q 240They may be the same or different. Q 250 This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between the carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O-, Q 10 Or Q 20 Q 250 If you have 2 or more Q 250 They may be the same or different. Q 260 This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between the carbon atoms. 6 -, -C(O)-, -NR 6 It is a group having - or -O-. Q 220 Q 230 Q 240 Q 250 and Q 260 The signs other than are the same as the signs in equations (g2-1) to (g2-7).

[0188] Q 220 -CH=CH2 is the Q in compound (1A) and compound (1B) after hydrosilylation. 22 This is the result. Q 220 Q 22 Similar groups can be cited, and the preferred forms are also similar. Q 230 -CH=CH2 is the Q in compound (1A) and compound (1B) after hydrosilylation. 23 This is the result. Q 230 Q 23 Similar groups can be cited, and the preferred forms are also similar. Q 240 -CH=CH2 is the Q in compound (1A) and compound (1B) after hydrosilylation. 24 This is the result. Q 240 Q 24 Similar groups can be cited, and the preferred forms are also similar. Q 250 -CH=CH2 is the Q in compound (1A) and compound (1B) after hydrosilylation. 25 This is the result. Q 250 Q 25Similar groups can be cited, and the preferred forms are also similar. Q 260 -CH=CH2 is the Q in compound (1A) and compound (1B) after hydrosilylation. 26 This is the result. Q 260 Q 26 Similar groups can be cited, and the preferred forms are also similar.

[0189] Q 10 [-CH=CH2] b1 Other forms include base(g4-8) (where a1=d1+d3 and b1=k), base(g4-9) (where a1=e1 and b1=k), base(g4-10) (where a1=1 and b1=k), base(g4-11) (where a1=h1 and b1=k), base(g4-12) (where a1=i1 and b1=k), base(g4-13) (where a1=1 and b1=k), or base(g4-14) (where a1=1 and b1=k). Q 20 [-CH=CH2] b2 Other forms of b4 include base(g4-8) (where b2=k), base(g4-9) (where b2=k), base(g4-10) (where b2=k), base(g4-11) (where b2=k), base(g4-12) (where b2=k), base(g4-13) (where b2=k), and base(g4-14) (where b2=k).

[0190] [ka]

[0191] (-AQ 12 -) e1 C(R 2 ) 4-e1-e2 (-Q 22 -G 1 ) e2 (g4-9) -AQ13 -N(-Q 23 -G 1 )2(g4-10) (-AQ 14 -) h1 Z(-Q 24 -G 1 ) h2 Formula (g4-11) (-AQ 15 -) i1 Si(R 3 ) 4-i1-i2 (-Q 25 -G 1 ) i2 (g4-12) -AQ 26 -G 1 (g4-13) -AQ 12 -CH(-Q 22 -G 1 )-Si(R 3 ) 3-i3 (-Q 25 -G 1 ) i3 (g4-14)

[0192] However, G 1 is the base (g5), Q 10 [-CH=CH2] b1 Or Q 20 [-CH=CH2] b2 2 or more G 1 They may be the same or different, G 1 The signs other than are the same as the signs in equations (g2-1) to (g2-7). -Si(R 8 ) 3-k (-Q 30 -CH=CH2) k (g5) However, Q 30 This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between the carbon atoms. 6 -, -C(O)-, -NR 6 A group having - or -O-, and two or more Q 30 Q can be the same or different, 30 The signs other than are the same as the signs in equation (g3). Q 30 -CH=CH2 is a group with Q in the (g3) group after hydrosilylation. 3 This is the result. Q 30 Q 3 Similar groups can be listed (however, -(OSi(R 9 )2) p (Excluding -O-), the same applies to preferred forms.

[0193] (Method for producing compound (2A) and compound (2B)) Q 10 [-CH=CH2] b1 Compound (2A) has (g4-1) as the base, and Q 20 [-CH=CH2] b2 Compound (2B) in which is the group (g4-1) is, for example, R f The precursor or Q of the part f Except for changing the method of producing the precursor of the part, it can be produced by the method described in International Publication No. 2017 / 187775. Q 10 [-CH=CH2] b1 Compound (2A) and Q, which have (g4-2) as the base. 20 [-CH=CH2] b2 Compound (2B) in which the group (g4-2) is, for example, R f The precursor or Q of the part f Except for changing the method of producing the precursor of the part, it can be produced by the method described in Japanese Patent Publication No. 2015-199906, the method described in Patent Document 1, the method described in Japanese Patent Publication No. 2016-204656, the method described in Japanese Patent Publication No. 2016-222859, the method described in Patent Document 2, the method described in International Publication No. 2017 / 187775, and the method described in International Publication No. 2019 / 039226. Q 10 [-CH=CH2] b1 Compound (2A) and Q, which have (g4-3) as the base. 20 [-CH=CH2] b2 Compound (2B) in which the group (g4-3) is, for example, R f The precursor or Q of the part fExcept for changing the method of producing the precursor of the part, it can be produced by the method described in International Publication No. 2017 / 038832. Q 10 [-CH=CH2] b1 Compound (2A) and Q, which have (g4-4) as the base. 20 [-CH=CH2] b2 Compound (2B) in which the group (g4-4) is, for example, R f The precursor or Q of the part f Except for changing the method of producing the precursor of the part, it can be produced by the method described in International Publication No. 2019 / 039186. Q 10 [-CH=CH2] b1 Compound (2A) and Q, which have (g4-5) as the base. 20 [-CH=CH2] b2 Compound (2B) in which the group (g4-5) is, for example, R f The precursor or Q of the part f Except for changing the method of producing the precursor of the part, it can be produced by the method described in Patent Document 1 or the method described in International Publication No. 2016 / 121211. Q 10 [-CH=CH2] b1 Compound (2A) and Q, which have (g4-6) as the base. 20 [-CH=CH2] b2 Compound (2B) in which the group (g4-6) is, for example, R f The precursor or Q of the part f Except for changing the method of producing the precursor of the part, it can be produced by the method described in Japanese Patent Publication No. 2012-072272, International Publication No. 2013 / 121984, and International Publication No. 2013 / 121986. Q 10 [-CH=CH2] b1 Compound (2A) and Q, which have (g4-7) as the base. 20 [-CH=CH2] b2 Compound (2B) in which the group (g4-7) is, for example, R f The precursor or Q of the part f Except for changing the method of producing the precursor of the part, it can be produced by the method described in International Publication No. 2019 / 163282. Q 10 [-CH=CH2] b1 Compound (2A) and Q, in which the group is (g4-8) to (g4-14). 20 [-CH=CH2] b2 Compound (2B) in which the group is (g4-8) to (g4-14) is, for example, R f The precursor or Q of the part f Except for changing the method of producing the precursor of the part, it can be produced by the method described in International Publication No. 2019 / 163282.

[0194] R of compound (2A) f A precursor for this part is, for example, compound (4A). Q of compound (2B) f A precursor to this part is, for example, compound (4B). R f -E 1 (4A) E 1 -Q f -E 1 (4B) However, E 1 -CH2-OH, -C(O)-X, -I, -OC(O)R f5 -SO2F, -CH2-SO2R f5 It is -CH2-NH2 or -CH2-O-CH2CH=CH2. X is a halogen atom, an alkoxy group, a hydroxyl group, or an amino group. f5 This is a perfluoroalkyl group or a perfluoroalkyl group having -O- between carbon atoms of a carbon atom with 2 or more carbon atoms. 1 , X and R f5 All other signs are the same as the signs in equations (2A) and (2B).

[0195] Examples of compounds (4A) and (4B) include, for example, the fluorine-containing compound (A), described later, having multiple -O- atoms between carbon atoms and an E at the terminal. 1If it has, a fluorine-containing compound (A) is an example. If the fluorine-containing compound (A), described later, does not have multiple -O- units between carbon atoms, then compound (4A) and compound (4B) are formed by starting with fluorine-containing compound (A), introducing one or more oxyfluoroalkylene units by known addition reactions, etc. to form a polyfluoropolyether chain, and then, if necessary, adding E to the end of the polyfluoropolyether chain by known methods, etc. 1 It can be manufactured by introducing [this technology].

[0196] E at the end of the polyfluoropolyether chain 1 Methods for implementing this include, for example, the method described in International Publication No. 2009 / 008380, the method described in International Publication No. 2013 / 121984, the method described in International Publication No. 2013 / 121986, the method described in International Publication No. 2015 / 087902, the method described in Patent Document 1, the method described in International Publication No. 2017 / 038832, the method described in International Publication No. 2018 / 143433, and the method described in International Publication No. 2018 / 216630.

[0197] As described above, the compound has monovalent or divalent polyfluoropolyether chains, and therefore can form a surface layer with excellent fingerprint stain removal properties. Furthermore, because this compound contains a reactive silyl group, it can form a surface layer with excellent abrasion resistance. Furthermore, in this compound, since the monovalent polyfluoropolyether chain has at least one of a monovalent fluorine-containing ring structure at the free end and a divalent fluorine-containing ring structure in the main chain, or the divalent polyfluoropolyether chain has a divalent fluorine-containing ring structure in the main chain, a surface layer with excellent slip resistance can be formed without reducing friction resistance and fingerprint stain removal properties.

[0198] [Method for producing fluorine-containing compounds] The following describes a method for producing fluorine-containing compounds useful as raw materials for this compound having a silyl group. However, some of the fluorine-containing compounds listed below may correspond to this compound having a functional group T other than a silyl group.

[0199] A first embodiment of a method for producing a fluorine-containing compound (hereinafter also referred to as "fluorine-containing compound (A)") having at least one of a monovalent four-membered fluorine-containing ring structure and a divalent four-membered fluorine-containing ring structure is a method of reacting compound (11) and compound (12) to obtain compound (21).

[0200] [ka]

[0201] However, R 11 This refers to an alkylene group, an alkylene group having 2 or more carbon atoms with an -O- between the carbon atoms, a fluoroalkylene group (where E is -OH, the E-side terminal is CH2), or a fluoroalkylene group having 2 or more carbon atoms with an -O- between the carbon atoms (where E is -OH, the E-side terminal is CH2). 12 is a halogen atom, a perfluoroalkyl group, or a group having -O- between carbon atoms of a perfluoroalkyl group having 2 or more carbon atoms. q is 0 or 1. E is -OH, -OR 14 , -SR 14 , -C(O)OR 14 -C(O)NHR 14 -C(O)NR 14 R 15 , -SO2X 1 , -C(O)X 1 , or a halogen atom. R 14 and R 15 These are each an alkyl group independently. 1 It is a halogen atom.

[0202] R 11 The number of carbon atoms in the alkylene group or fluoroalkylene group is preferably 1 to 10, more preferably 1 to 8, and particularly preferably 2 to 6, from the standpoint of facilitating the production of fluorine-containing compound (A). However, the lower limit of the number of carbon atoms in the alkylene group or fluoroalkylene group when there is an -O- between carbon atoms is 2. R 11Examples include -CH2-, -CH2CH2-, -CHF-, -CF2CH2-, -CF2CF2CF2CH2-, -CF2-, -CF2CF2-, -CF2CF2OCF2-, -CF(CF3)CF2OCF(CF3)-, and -CF2CF2CF2CF2CF2CH2-.

[0203] Examples of compound (11) include the following compounds. CF2 = CFOCF3, CF2 = CFOCF2CF3, CF2 = CFOCF2CF2CF3, CF2=CFOCF2CF(CF3)OCF2CF2CF3, CF2=CFOCF2CF(CF3)OCF2CF(CF3)OCF2CF2CF3, CF2=CFOCF2CF(CF3)OCF2CF2SO2F, CF2=CFOCF2CFCF2CONH2, CF2=CFOCF2CF2CF2CH2OCF2CHFOCF3, CF2=CFOCF2CF2CF2CH2OCF2CHFOCF2CF3, CF2=CFOCF2CF2CF2CH2OCF2CHFOCF2CF2CF3, CF2=CFOCF2CF2CF2CF2CF2CH2OCF2CHFOCF3, CF2=CFOCF2CF2CF2CF2CF2CH2OCF2CHFOCF2CF3, CF2=CFOCF2CF2CF2CF2CF2CH2OCF2CHFOCF2CF2CF3, CF2=CFOCF2CF2CF2OCHFCF2OCH3, CF2=CFOCF2CF2CF2OCHFCF2OCH2CH3, CF2=CFOCF2CF2CF2OCHFCF2OCH2CH2CH3, CF2=CFOCF2CF2CF2OCHFCF2OCH2CH2CH2CH3, CF2=CFOCF2CF2CF2OCHFCF2OCH2CH2CH2CH2CH3, CF2=CFOCF2CF2CF2OCHFCF2OCH2CH2CH2CH2CH2CH3、 CF2=CFOCF2CF2CF2CF2OCHFCF2OCH3、 CF2=CFOCF2CF2CF2CF2OCHFCF2OCH2CH3、 CF2=CFOCF2CF2CF2CF2OCHFCF2OCH2CH2CH3、 CF2=CFOCF2CF2CF2CF2OCHFCF2OCH2CH2CH2CH3、 CF2=CFOCF2CF2CF2CF2OCHFCF2OCH2CH2CH2CH2CH3、 CF2=CFOCF2CF2CF2CF2OCHFCF2OCH2CH2CH2CH2CH2CH3、 CF2=CFOCF2CF2CF2CF2CF2OCHFCF2OCH3、 CF2=CFOCF2CF2CF2CF2CF2OCHFCF2OCH2CH3、 CF2=CFOCF2CF2CF2CF2CF2OCHFCF2OCH2CH2CH3、 CF2=CFOCF2CF2CF2CF2CF2OCHFCF2OCH2CH2CH2CH3、 CF2=CFOCF2CF2CF2CF2CF2OCHFCF2OCH2CH2CH2CH2CH3、 CF2=CFOCF2CF2CF2CF2CF2OCHFCF2OCH2CH2CH2CH2CH2CH3、 CF2=CFOCF2CF2CF2CF2CF2CF2OCHFCF2OCH3、 CF2=CFOCF2CF2CF2CF2CF2CF2OCHFCF2OCH2CH3、 CF2=CFOCF2CF2CF2CF2CF2CF2OCHFCF2OCH2CH2CH3、 CF2=CFOCF2CF2CF2CF2CF2CF2OCHFCF2OCH2CH2CH2CH3、 CF2=CFOCF2CF2CF2CF2CF2CF2OCHFCF2OCH2CH2CH2CH2CH3、 CF2=CFOCF2CF2CF2CF2CF2CF2OCHFCF2OCH2CH2CH2CH2CH2CH3、 CF2=CFOCF2CF2CF2CF2CF2CH2OH、 CF2=CFOCF2CF2CF2CF2CF2COOCH3、 CF2=CFOCF2CF2CF2CF2CF2CONHCH3、 CF2=CFOCF2CF2CF2CF2CF2CONH2、 CF2=CFOCF2CF2CF2CF2CF2SO2F、 CF2=CFOCF2C(CF2OCF2CF2SO2F)FOCF2CF2SO2F、 CF2=CFOCF2CF2SO2F、 CF2=CFOCF2CF2CF2CF2SO2F、 CF2=CF-O-CF2CF2CF2CH2-OH、 CF2=CF-O-CF2CF2CF2-C(O)OCH3、 CF2=CF-O-CF2CF2CF2-C(O)NHCH3、 CF2=CF-O-CF2CF2CF2-C(O)N(CH3)2、 CF2=CF-O-CF2CF2CF2-SO2F、 CF2=CF-O-CF2CF2CF2CF2-F、 CF2=CF-O-CF2CF2CF2CF2-Cl、 CF2=CF-O-CF2CF2CF2CF2-Br、 CF2=CF-O-CF2CF2CF2CF2-I、 CF2=CF-O-CF2CF2CF2CH2-OCH3、 CF2=CF-O-CF2CF2CF2-C(O)F、 CF2=CF-O-CF2CF2CF2CF2OCHFCF2-OCH3。

[0204] R 12The number of carbon atoms in the perfluoroalkyl group is preferably 1 to 10, more preferably 1 to 8, and particularly preferably 1 to 6, from the standpoint of facilitating the production of fluorine-containing compound (A). However, the lower limit of the number of carbon atoms in the perfluoroalkyl group when there is an -O- between carbon atoms is 2. R 12 As the halogen atom, a fluorine atom or a chlorine atom is preferred because it facilitates the production of fluorine-containing compounds (A). R 12 Examples include -F, -Cl, -CF3, -CF2CF3, -CF2CF2OCF3, and -CF(CF3)CF2CF3. Examples of compound (12) include CF2=CF2, CF2=CF-CF3, CF2=CF-CF2CF3, and CF2=CF-CF(CF3)2.

[0205] R 14 or R 15 The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 8, and particularly preferably 1 to 6, from the standpoint of facilitating the production of fluorine-containing compound A. X 1 As such, fluorine atoms or chlorine atoms are preferred because they facilitate the production of fluorine-containing compounds (A).

[0206] Compound (21) can be produced, for example, by charging compound (11) and compound (12) into a reaction vessel and heating it. Examples of reaction vessels include metal containers (such as stainless steel). The reaction temperature is, for example, 150-250°C. The reaction time is, for example, 50 to 300 hours. The reaction pressure is, for example, above atmospheric pressure and below 2.0 MPa (gauge), and preferably below 0.2 MPa.

[0207] A second aspect of the method for producing the fluorine-containing compound (A) is a method of reacting compound (11) and compound (13) to obtain compound (22).

[0208] [ka]

[0209] However, R 13 R is a fluoroalkylene group, a group having -O- at both ends of a fluoroalkylene group, or a group having -O- between carbon atoms of a fluoroalkylene group having 2 or more carbon atoms. 13 The signs other than are the same as the signs in equation (11), and the preferred form is also the same. 11 q and E may be the same or different. If compound (11) is a single compound, the resulting compound (22) has multiple R in formula (22). 11 In this case, the same compound is obtained for both E and q. On the other hand, when compound (11) is a combination of multiple compounds, the resulting compound (22) has multiple R in formula (22). 11 , containing at least one different compound among E and q.

[0210] R 13 The number of carbon atoms in the fluoroalkylene group is preferably 0 to 10, more preferably 1 to 8, and particularly preferably 1 to 6, from the standpoint of facilitating the production of fluorine-containing compound (A). However, the lower limit of the number of carbon atoms in the fluoroalkylene group when there is an -O- between carbon atoms is 2. R 13 Examples include -CF2-, -CF2CF2-, -CF(CF3)CF2-, -CF2CH2CF2-, -OCF2CF2CF2O-, and -CF2OCF2CF2OCF2-.

[0211] Examples of compound (13) include CF2=CF-OCF2CF2CF2O-CF=CF2, CF2=CF-OCF2-CF=CF2, CF2=CF-OCF2CF2CF2CF2O-CF=CF2, CF2=CFOCF2CF2OCF=CF2, CF2=CFOCF2CF2CF2CF2CF2CF2OCF=CF2, CF2=CFOCF2OCF2OCF2OCF=CF2, CF2=CFOCF2CF2OCF2CF2OCF=CF2, and CF2=CFOCF2CF2OCF2CF2OCF2CF2OCF=CF2. Compound (22) can be prepared in the same manner as compound (21).

[0212] A third aspect of the method for producing the fluorine-containing compound (A) is a method of reacting compounds (11) together to obtain compound (23).

[0213] [ka]

[0214] However, the signs in formula (23) are the same as the signs in formula (11), and the preferred form is also the same. Compound (23) can be prepared in the same manner as compound (21). Note that compound (11) may be a single compound or a combination of multiple compounds corresponding to formula (11). If compound (11) is a single compound, the resulting compound (23) will have multiple R compounds in formula (23). 11 In this case, the same compound is obtained for both E and q. On the other hand, when compound (11) is a combination of multiple compounds, the resulting compound (23) has multiple R in formula (23). 11 , containing at least one different compound among E and q.

[0215] A fourth aspect of the method for producing the fluorine-containing compound (A) is a method of reacting compounds (13) together to obtain compound (24).

[0216] [ka]

[0217] However, r is an integer greater than or equal to 1. The signs of the other elements are the same as the signs in equation (13), and the preferred form is also the same. r is preferably an integer between 1 and 100, and particularly preferably an integer between 2 and 20. Compound (24) can be prepared in the same manner as compound (21). Note that compound (13) may be a single compound or a combination of multiple compounds corresponding to formula (13). If compound (13) is a single compound, the resulting compound (24) will have multiple R compounds in formula (24). 13 The same compound is obtained. On the other hand, if compound (13) is a combination of multiple compounds, the resulting compound (24) has multiple R in formula (24). 13 It contains different compounds.

[0218] A fifth aspect of the method for producing the fluorine-containing compound (A) is a method of reacting compound (11) and compound (13) to obtain compound (25).

[0219] [ka] However, the symbols in formula (25) are the same as the symbols in formulas (11), (13), and (24), and the preferred form is also the same. Compound (25) can be prepared in the same manner as compound (21).

[0220] A sixth aspect of the method for producing the fluorine-containing compound (A) is a method of reacting compounds (12) together to obtain compound (26).

[0221] [ka] However, the signs in formula (26) are the same as the signs in formula (12), and the preferred form is also the same. Compound (26) can be prepared in the same manner as compound (21). Note that compound (12) may be a single compound or a combination of multiple compounds corresponding to formula (12). If compound (12) is a single compound, the resulting compound (26) will have multiple R compounds in formula (26). 12 The same compound is obtained. On the other hand, if compound (12) is a combination of multiple compounds, the resulting compound (23) will have multiple R in formula (23). 12 It contains different compounds.

[0222] A seventh aspect of the method for producing the fluorine-containing compound (A) is a method of reacting compound (12) and compound (13) to obtain compound (27).

[0223] [ka] However, r² is an integer greater than or equal to 1. The signs of the other terms are the same as the signs in equations (12) and (13), and the preferred form is also the same. r² is preferably an integer between 1 and 100, and particularly preferably an integer between 2 and 20. Compound (27) can be prepared in the same manner as compound (21).

[0224] [Fluorine-containing compound-containing composition] The fluorine-containing compound-containing composition of the present invention (hereinafter also referred to as "this composition") comprises one or more fluorine-containing ether compounds that are the present compound, and other fluorine-containing ether compounds other than the present compound. This composition may contain, for example, both compound (1A) and compound (1B) as the present compound. This composition does not contain the liquid medium described later.

[0225] Other fluorine-containing ether compounds include both compounds that are inevitably included and compounds that are used in combination depending on the application.

[0226] Examples of compounds that can be used in combination with this compound include known fluorine-containing ether compounds and fluorine-containing oils.

[0227] Examples of fluorinated oils include polytetrafluoroethylene (PTFE), ethylene-chlorotrifluoroethylene copolymer (ECTFE), polyvinylidene fluoride (PVDF), polyvinyl fluoride (PVF), and polychlorotrifluoroethylene (PCTFE).

[0228] Furthermore, known fluorine-containing ether compounds include, for example, fluorine-containing ether compounds that are commercially available as surface treatment agents. When this composition contains known fluorine-containing ether compounds, new effects such as complementing the properties of this compound may be exhibited. Examples of known fluorine-containing ether compounds include those described in the following literature. Perfluoropolyether-modified aminosilane as described in Japanese Patent Publication No. 11-029585, Silicon-containing organic fluorine polymer as described in Japanese Patent Publication No. 2874715, Organosilicon compounds described in Japanese Patent Publication No. 2000-144097, Perfluoropolyether-modified aminosilane as described in Japanese Patent Publication No. 2000-327772, Fluorinated siloxane as described in Japanese Patent Publication No. 2002-506887, Organic silicone compounds described in Japanese Patent Publication No. 2008-534696, Fluorinated modified hydrogen-containing polymer as described in Japanese Patent Publication No. 4138936, The compounds described in U.S. Patent Application Publication No. 2010 / 0129672, International Publication No. 2014 / 126064, and Japanese Patent Publication No. 2014-070163, Organosilicon compounds described in International Publication No. 2011 / 060047 and International Publication No. 2011 / 059430, Fluorine-containing organosilane compounds described in International Publication No. 2012 / 064649, A fluorooxyalkylene group-containing polymer described in Japanese Patent Publication No. 2012-72272, Fluorine-containing ether compounds as described in International Publication No. 2013 / 042732, International Publication No. 2013 / 121984, International Publication No. 2013 / 121985, International Publication No. 2013 / 121986, International Publication No. 2014 / 163004, Japanese Patent Publication No. 2014-080473, International Publication No. 2015 / 087902, International Publication No. 2017 / 038830, International Publication No. 2017 / 038832, and International Publication No. 2017 / 187775. Perfluoro(poly)ether-containing silane compounds described in Japanese Patent Publication No. 2014-218639, International Publication No. 2017 / 022437, International Publication No. 2018 / 079743, and International Publication No. 2018 / 143433. Fluoropolyether group-containing polymer-modified silanes as described in Japanese Patent Publication No. 2015-199906, Japanese Patent Publication No. 2016-204656, Japanese Patent Publication No. 2016-210854, and Japanese Patent Publication No. 2016-222859. Fluorine-containing ether compounds as described in International Publication No. 2018 / 216630, International Publication No. 2019 / 039226, International Publication No. 2019 / 039341, International Publication No. 2019 / 039186, International Publication No. 2019 / 044479, Japanese Patent Publication No. 2019-44158, International Publication No. 2019 / 044479, and International Publication No. 2019 / 163282. Furthermore, commercially available fluorine-containing compounds include the KY-100 series (KY-178, KY-185, KY-195, etc.) from Shin-Etsu Chemical Co., Ltd., Afluid® S550 from AGC Inc., and Optool® DSX, Optool® AES, Optool® UF503, and Optool® UD509 from Daikin Industries, Ltd.

[0229] In this composition, when combining this compound with a known fluorine-containing ether compound, the content ratio may be adjusted as appropriate depending on the application. The content of this compound in this composition is preferably 10 to 90% by mass, more preferably 20 to 80% by mass, and even more preferably 25 to 75% by mass. By setting the content within the above range, the properties of this compound can be fully exhibited, and the properties of the fluorine-containing ether compound used in combination can also be fully obtained.

[0230] Compounds that are inevitably included include fluorine-containing ether compounds (hereinafter also referred to as "by-product fluorine-containing ether compounds") that are produced as by-products during the manufacturing process of this compound. Examples of by-product fluorine-containing ether compounds include unreacted fluorine-containing compounds (e.g., compound (2A) or compound (2B)), and fluorine-containing ether compounds in which some of the allyl groups are isomerized to inner olefins during hydrosilylation in the production of this compound.

[0231] If the composition contains a by-product fluorine-containing ether compound, it is possible to remove the by-product fluorine-containing ether compound by purification. However, it may be included in the composition to the extent that the properties of the compound can be fully exhibited. This simplifies the purification process for the by-product fluorine-containing ether compound. When not combined with known fluorine-containing ether compounds, the content of this compound in the composition is preferably 60% by mass or more and less than 100% by mass, more preferably 70% by mass or more and less than 100% by mass, and particularly preferably 80% by mass or more and less than 100% by mass. The content of the by-product fluorine-containing ether compound is preferably greater than 0% by mass and 40% by mass or less of the composition, more preferably greater than 0% by mass and 30% by mass or less, and particularly preferably greater than 0% by mass and 20% by mass or less. If the content of this compound and the content of the by-product fluorine-containing ether compound are within the above range, the initial water- and oil-repellent properties, abrasion resistance, fingerprint stain removal properties, light resistance, and chemical resistance of the surface layer are further improved.

[0232] In addition, additives such as acid catalysts and basic catalysts that promote the hydrolysis and condensation reactions of hydrolyzable silyl groups are inevitably included. Examples of acid catalysts include hydrochloric acid, nitric acid, acetic acid, sulfuric acid, phosphoric acid, sulfonic acid, methanesulfonic acid, and p-toluenesulfonic acid. Examples of basic catalysts include sodium hydroxide, potassium hydroxide, and ammonia. The content of these components is preferably 0 to 9.999% by mass, and particularly preferably 0 to 0.99% by mass, of the composition.

[0233] [Coating liquid] The coating solution of the present invention (hereinafter also referred to as "the coating solution") comprises the compound or composition and a liquid medium. The coating solution may be a solution or a dispersion.

[0234] An organic solvent is preferred as the liquid medium. The organic solvent may be a fluorine-containing organic solvent or a non-fluorine organic solvent, or it may contain both. Examples of fluorine-containing organic solvents include fluorinated alkanes, fluorinated aromatic compounds, fluoroalkyl ethers, fluorinated alkylamines, and fluoroalcohols. As the fluorinated alkane, compounds with 4 to 8 carbon atoms are preferred. A commercially available example is C6F 13 H (manufactured by AGC Corporation, Asahi Clean® AC-2000), C6F 13 Examples include C2H5 (manufactured by AGC, Asahi Clean® AC-6000) and C2F5CHFCHFCF3 (manufactured by Chemours, Bartrell® XF). Examples of fluorinated aromatic compounds include hexafluorobenzene, trifluoromethylbenzene, perfluorotoluene, and bis(trifluoromethyl)benzene. As fluoroalkyl ethers, compounds having 4 to 12 carbon atoms are preferred. Examples of commercially available products include CF3CH2OCF2CF2H (manufactured by AGC, Asahi Clean® AE-3000), C4F9OCH3 (manufactured by 3M, Novec® 7100), C4F9OC2H5 (manufactured by 3M, Novec® 7200), and C2F5CF(OCH3)C3F7 (manufactured by 3M, Novec® 7300). Examples of fluorinated alkylamines include perfluorotripropylamine and perfluorotributylamine. Examples of fluoroalcohols include 2,2,3,3-tetrafluoropropanol, 2,2,2-trifluoroethanol, and hexafluoroisopropanol. Preferred non-fluorine organic solvents include compounds consisting only of hydrogen atoms and carbon atoms, and compounds consisting only of hydrogen atoms, carbon atoms, and oxygen atoms, and examples include hydrocarbons, alcohols, ketones, ethers, and esters. The liquid medium may be a mixed medium obtained by mixing two or more types.

[0235] The content of this compound or composition is preferably 0.001 to 10% by mass, and particularly preferably 0.01 to 1% by mass, of the coating solution. The liquid medium content of the coating solution is preferably 90 to 99.999% by mass, and particularly preferably 99 to 99.99% by mass.

[0236] [Goods] The article of the present invention (hereinafter also referred to as "the Article") has a surface layer formed from the Compound or Composition on the surface of a substrate. The surface layer may be formed on a part of the surface of the substrate or on the entire surface of the substrate. The surface layer may spread as a film on the surface of the substrate or may be scattered as dots. When using the compound having a silyl group, the surface layer contains the compound in a state in which some or all of the hydrolyzable silyl groups of the compound have undergone hydrolysis and the silanol groups have undergone dehydration condensation.

[0237] The surface layer thickness is preferably 1 to 100 nm, and particularly preferably 1 to 50 nm. If the surface layer thickness is 1 nm or more, the effects of the surface treatment are easily obtained. If the surface layer thickness is 100 nm or less, the utilization efficiency is high. The surface layer thickness can be calculated from the vibration period of the interference pattern obtained by the X-ray reflectivity method using a thin-film analysis X-ray diffractometer (RIGAKU Corporation, ATX-G).

[0238] Examples of substrates include those for which water-repellent and oil-repellent properties are required. These include substrates that may come into contact with other items (e.g., styluses) or people's fingers during use, substrates that may be held by people's fingers during operation, and substrates that may be placed on other items (e.g., stands). Examples of substrate materials include metals, resins, glass, sapphires, ceramics, stones, and composite materials thereof. The glass may be chemically strengthened. An undercoat, such as an SiO2 film, may be formed on the surface of the substrate. Suitable substrates include touch panel substrates, display substrates, and eyeglass lenses, with touch panel substrates being particularly preferred. Glass and transparent resins are preferred materials for the touch panel substrates. Furthermore, glass and resin films used as substrates are also preferred for use in the exterior parts (excluding the display) of devices such as mobile phones (e.g., smartphones), personal digital assistants (e.g., tablet devices), game consoles, and remote controls.

[0239] [Method of manufacturing articles] This article can be manufactured, for example, by the following method. A method for treating the surface of a substrate by a dry coating method using the compound or composition, thereby forming a surface layer on the surface of the substrate that is made of compound (1A) or compound (1B) or the composition. A method of applying the coating liquid to the surface of a substrate by a wet coating method and drying it to form a surface layer on the surface of the substrate that is made of the compound or composition.

[0240] Examples of dry coating methods include vacuum deposition, CVD, and sputtering. Vacuum deposition is preferred as a dry coating method due to its ability to suppress the decomposition of the compound and its simplicity of equipment. During vacuum deposition, pellet-like material impregnated with the compound or composition may be used in porous metal materials such as iron or steel. Alternatively, the coating solution may be impregnated into porous metal materials such as iron or steel, the liquid medium may be dried, and pellet-like material impregnated with the compound or composition may be used.

[0241] Examples of wet coating methods include spin coating, wipe coating, spray coating, squeegee coating, dip coating, die coating, inkjet coating, flow coating, roll coating, cast coating, Langmuir-Bludget coating, and gravure coating. [Examples]

[0242] The present invention will be described in more detail below using examples, but the present invention is not limited to these examples. In the following, "%" refers to "mass%" unless otherwise specified. Examples 1-4, 7-10, and 13-16 are examples relating to the compound having a reactive silyl group, while Examples 5, 6, 11, and 12 are comparative examples. More specifically, Examples 1-3 to 1-8, 2-2 to 2-7, 3-2 to 3-7, 4-1 to 4-6, 14-2 to 14-7, and 15-2 to 15-7 are examples illustrating the synthesis method of fluorine-containing ether compounds according to the present invention.

[0243] [Example 1] (Example 1-1) Compound (11-1) was obtained according to the method described in Example 1-1 of International Publication No. 2013-121984. CF2=CF-O-CF2CF2CF2CH2-OH (11-1)

[0244] (Examples 1-2) 10 g of compound (11-1) obtained in Example 1-1 was placed in a 100 mL metal reactor and stirred at 175 °C for 200 hours. The resulting organic phase was concentrated to obtain 6 g of compound (23-1).

[0245] [ka]

[0246] NMR spectrum of compound (23-1); 1 ¹H-NMR (300.4 MHz, solvent: CDCl3, reference: tetramethylsilane (TMS)) δ (ppm): 4.1 (4H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -80 (2F), -85 (2F), -123 (4F), -126 (4F), -128 (2F), -131 (2F), -137 (1F), -139 (1F).

[0247] (Examples 1-3) In a 200 mL round-bottom flask, 5 g of compound (23-1) obtained in Example 1-2 and 1.2 g of potassium carbonate were placed and stirred at 120°C. Then, 25 g of compound (11-1) was added and the mixture was stirred at 120°C for 2 hours. The temperature in the round-bottom flask was reduced to 25°C, 30 g each of AC-2000 and hydrochloric acid were added, and the mixture was separated to concentrate the organic phase. The resulting crude reaction solution was purified by column chromatography to obtain 21 g of compound (4-1).

[0248] [ka]

[0249] NMR spectrum of compound (4-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.0 (10H), 4.6 (20H), 4.1 (4H). 19F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -80 (2F), -85 (22F), -91 (20F), -120 (20F), -123 (4F), -126 (24F), -128 (2F), -131 (2F), -137 (1F), -139 (1F), -144 (10F). The average value of x1 + x2 is 10.

[0250] (Examples 1-4) 20 g of compound (4-1) obtained in Example 1-3, 7.1 g of sodium fluoride powder, 20 g of AC-2000, and 20 g of CF3CF2CF2OCF(CF3)COF were added to a 50 mL round-bottom flask. The mixture was stirred at 50°C for 24 hours under a nitrogen atmosphere. After the temperature in the round-bottom flask was reduced to 25°C, the sodium fluoride powder was removed by filtration. The excess CF3CF2CF2OCF(CF3)COF and AC-2000 were removed by distillation under reduced pressure to obtain 24 g of compound (4-2).

[0251] [ka]

[0252] NMR spectrum of compound (4-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.0 (10H), 5.0 (4H), 4.6 (20H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -79 (4F), -80 (2F), -81 (6F), -82 (6F), -85 (22F), -91 (20F), -119 (4F), -120 (20F), -126 (24F), -128 (2F), -129 (4F), -131 (2F), -131 (2F), -137 (1F), -139 (1F), -144 (10F). The average value of x1 + x2 is 10.

[0253] (Examples 1-5) 250 mL of ClCF2CFClCF2OCF2CF2Cl (hereinafter referred to as "CFE-419") was added to a 500 mL metal reactor, and nitrogen gas was bubbled in. Then, 20 vol% fluorine gas diluted with nitrogen gas was bubbled in. A CFE-419 solution of compound (4-2) obtained in Example 1-4 (concentration: 10%, compound (4-2): 20 g) was added over 3 hours. The ratio of the fluorine gas introduction rate (mol / hour) to the hydrogen atom introduction rate in compound (4-2) (mol / hour) was controlled to 2:1. After the addition of compound (4-2) was complete, a CFE-419 solution of benzene (concentration: 0.1%, benzene: 0.1 g) was added intermittently. After the addition of benzene was complete, fluorine gas was bubbled in, and finally the reactor was thoroughly purged with nitrogen gas. The solvent was removed by distillation to obtain 21 g of compound (4-3).

[0254] [ka]

[0255] NMR spectrum of compound (4-3); 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -79 (4F), -80 (2F), -81 (6F), -82 (6F), -83 (46F), -87 (40F), -124 (48F), -128 (2F), -129 (4F), -131 (2F), -131 (2F), -137 (1F), -139 (1F). The average value of x1 + x2 is 10.

[0256] (Examples 1-6) In a 50 mL round-bottom flask, 20 g of compound (4-3) obtained in Example 1-5, 1.8 g of sodium fluoride, and 20 mL of AC-2000 were placed and stirred in an ice bath. 1.4 g of methanol was added and stirred at 25°C for 1 hour. After filtration, the filtrate was purified by column chromatography. 14 g of compound (4-4) was obtained.

[0257] [ka]

[0258] NMR spectrum of compound (4-4); 1 1H-NMR (300.4 MHz, solvent: CDCl3, reference: TMS) δ (ppm): 4.2 (6H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -80 (2F), -83 (42F), -87 (40F), -119 (4F), -124 (44F), -128 (2F), -131 (2F), -137 (1F), -139 (1F). The average value of x1 + x2 is 10.

[0259] (Examples 1-7) In a 50 mL round-bottom flask, 12 g of compound (4-4) obtained in Example 1-6, 1.5 g of H2NCH2C(CH2CH=CH2)3, and 12 mL of AC-2000 were placed and stirred at 0°C for 24 hours. The crude reaction solution was purified by column chromatography. 9 g of compound (2-1) was obtained.

[0260] [ka]

[0261] NMR spectrum of compound (2-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.1 (6H), 5.2 (12H), 3.4 (4H), 2.1 (12H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -80 (2F), -83 (42F), -87 (40F), -120 (4F), -124 (44F), -128 (2F), -131 (2F), -137 (1F), -139 (1F). The average value of x1 + x2 is 10.

[0262] (Examples 1-8) In a 50 mL round-bottom flask, 1 g of compound (2-1) obtained in Example 1-7, 0.21 g of trimethoxysilane, 0.001 g of aniline, 1.0 g of AC-6000, and 0.0033 g of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex were placed and stirred overnight at 25°C. The solvent and other substances were removed by distillation under reduced pressure to obtain 1.2 g of compound (1-1).

[0263] [ka]

[0264] NMR spectrum of compound (1-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.6 (54H), 3.4 (4H), 1.3 (24H), 0.9 (12H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -80 (2F), -83 (42F), -87 (40F), -120 (4F), -124 (44F), -128 (2F), -131 (2F), -137 (1F), -139 (1F). The average value of x1 + x2 is 10.

[0265] [Example 2] (Example 2-1) 20 g of compound (11-1) obtained in Example 1-1 was placed in a 100 mL metal reactor, and 7.2 g of CF2=CF2 was added. The mixture was stirred at 180 °C for 300 hours. The resulting organic phase was concentrated to obtain 8 g of compound (21-1).

[0266] [ka]

[0267] NMR spectrum of compound (21-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 4.1 (2H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -80 (2F), -123 (2F), -126 (2F), -128 (2F), -130 (4F), -137 (1F).

[0268] (Example 2-2) Compound (4-5) was obtained in the same manner as in Example 1-3, except that compound (23-1) was replaced with 3.4 g of compound (21-1) obtained in Example 2-1, and potassium carbonate was changed to 0.6 g.

[0269] [ka]

[0270] NMR spectra of compounds (4-5); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.0 (10H), 4.6 (20H), 4.1 (2H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -80 (2F), -85 (20F), -91 (20F), -120 (20F), -123 (2F), -126 (22F), -128 (2F), -130 (4F), -137 (1F), -144 (10F). The mean value of x is 10.

[0271] (Example 2-3) Compound (4-6) was obtained in the same manner as in Example 1-4, except that compound (4-1) was replaced with 16 g of compound (4-5) obtained in Example 2-2, the amount of sodium fluoride powder was changed to 3.5 g, and the amount of CF3CF2CF2OCF(CF3)COF was changed to 10 g.

[0272] [ka]

[0273] NMR spectra of compounds (4-6); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.0 (10H), 5.0 (2H), 4.6 (20H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -79 (2F), -80 (2F), -81 (3F), -82 (3F), -85 (20F), -91 (20F), -119 (2F), -120 (20F), -126 (22F), -128 (2F), -129 (2F), -130 (4F), -131 (1F), -137 (1F), -144 (10F). The mean value of x is 10.

[0274] (Examples 2-4) Compound (4-7) was obtained in the same manner as in Example 1-5, except that compound (4-2) was replaced with 18 g of compound (4-6) obtained in Example 2-3.

[0275] [ka]

[0276] NMR spectra of compounds (4-7); 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -79 (2F), -80 (2F), -81 (3F), -82 (3F), -83 (42F), -87 (40F), -124 (44F), -128 (2F), -129 (2F), -130 (4F), -131 (1F), -137 (1F). The mean value of x is 10.

[0277] (Examples 2-5) 14 g of compound (4-8) was obtained in the same manner as in Example 1-6, except that compound (4-3) was replaced with 19 g of compound (4-7) obtained in Example 2-4.

[0278] [ka]

[0279] NMR spectra of compounds (4-8); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 4.2 (3H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -80 (2F), -83 (40F), -87 (40F), -119 (2F), -124 (42F), -128 (2F), -130 (4F), -137 (1F). The mean value of x is 10.

[0280] (Examples 2-6) 10 g of compound (2-2) was obtained in the same manner as in Example 1-7, except that compound (4-4) was replaced with 14 g of compound (4-8) obtained in Example 2-5.

[0281] [ka]

[0282] NMR spectrum of compound (2-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.1 (3H), 5.2 (6H), 3.4 (2H), 2.1 (6H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -80 (2F), -83 (40F), -87 (40F), -120 (2F), -124 (42F), -128 (2F), -130 (4F), -137 (1F). The mean value of x is 10.

[0283] (Examples 2-7) 1.1 g of compound (1-2) was obtained in the same manner as in Example 1-8, except that compound (2-1) was replaced with 1 g of compound (2-2) obtained in Example 2-6.

[0284] [ka]

[0285] NMR spectra of compounds (1-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.6 (27), 3.4 (2H), 1.3 (12H), 0.9 (6H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -80 (2F), -83 (40F), -87 (40F), -120 (2F), -124 (42F), -128 (2F), -130 (4F), -137 (1F). The mean value of x is 10.

[0286] [Example 3] (Example 3-1) 39.4 g of CF2=CFOCF2CF2CF2CF2OCF=CF2, 3.2 g of methanol, and 13.8 g of potassium carbonate were placed in a 500 mL round-bottom flask and stirred at 40°C for 2 hours. Hydrochloric acid was added, and the organic phase obtained by liquid-liquid separation was dehydrated with magnesium sulfate. After filtering off the magnesium sulfate, the crude liquid was distilled to obtain 17.0 g of compound (11-2).

[0287] [ka]

[0288] NMR spectrum of compound (11-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.0 (1H), 3.4 (3H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -82 (4F), -90 (2F), -114 (1F), -122 (1F), -124 (4F), -135 (1F), -144 (1F).

[0289] (Example 3-2) In a 200 mL metal reactor, 15 g of compound (11-2) obtained in Example 3-1 was added, along with 138 g of CF2=CFOCF2CF2CF2CF2OCF=CF2, and the mixture was stirred at 160°C for 300 hours. The reactor temperature was reduced to 25°C, and 9.8 g of compound (11-1) obtained in Example 1-1 was added, and the mixture was stirred at 180°C for 100 hours. The reactor temperature was reduced to 25°C, and the resulting crude reaction solution was purified by column chromatography to obtain 9.8 g of compound (4-9).

[0290] [ka]

[0291] NMR spectra of compounds (4-9); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.0 (1H), 4.0 (2H), 3.4 (3H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -82 (44F), -85 (2F), -90 (2F), -123 (2F), -124 (44F), -126 (2F), -128 (22F), -131 (22F), -137 (11F), -139 (11F), -144 (1F). The mean value of x is 11.

[0292] (Example 3-3) Except for changing compound (4-1) to 9 g of compound (4-9) obtained in Example 3-2, changing the sodium fluoride powder to 0.4 g, and changing the CF3CF2CF2OCF(CF3)COF to 3.2 g, 10 g of compound (4-10) was obtained in the same manner as in Example 1-4.

[0293] [ka]

[0294] NMR spectra of compounds (4-10); 1H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.0 (1H), 5.0 (2H), 3.4 (3H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -79 (2F), -81 (3F), -82 (47F), -85 (2F), -90 (2F), -119 (2F), -124 (44F), -126 (2F), -128 (22F), -129 (2F), -131 (23F), -137 (11F), -139 (11F), -144 (1F). The mean value of x is 11.

[0295] (Example 3-4) Compound (4-11) was obtained in the same manner as in Example 1-5, except that compound (4-2) was replaced with 10 g of compound (4-10) obtained in Example 3-3, and the time of infusion of compound (4-10) into the CFE-419 solution was changed to 2 hours.

[0296] [ka]

[0297] NMR spectra of compounds (4-11); 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -55 (3F), -79 (2F), -81 (3F), -82 (51F), -87 (4F), -124 (48F), -128 (22F), -129 (2F), -131 (23F), -137 (11F), -139 (11F). The mean value of x is 11.

[0298] (Examples 3-5) In a 50 mL round-bottom flask, 9 g of compound (4-11) obtained in Example 3-4, 0.4 g of sodium fluoride, and 10 mL of AC-2000 were placed and stirred in an ice bath. 0.3 g of methanol was added and stirred at 25°C for 1 hour. After filtration, the filtrate was purified by column chromatography. 6.7 g of compound (4-12) was obtained.

[0299] [ka]

[0300] NMR spectra of compounds (4-12); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 4.2 (3H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -55 (3F), -82 (46F), -87 (4F), -119 (2F), -124 (46F), -128 (22F), -131 (22F), -137 (11F), -139 (11F). The mean value of x is 11.

[0301] (Examples 3-6) In a 50 mL round-bottom flask, 6 g of compound (4-12) obtained in Example 3-5, 0.4 g of H2NCH2C(CH2CH=CH2)3, and 6 mL of AC-2000 were placed and stirred at 0°C for 24 hours. The crude reaction solution was purified by column chromatography. 4.3 g of compound (2-3) was obtained.

[0302] [ka]

[0303] NMR spectra of compounds (2-3); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.1 (3H), 5.2 (6H), 3.4 (2H), 2.1 (6H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -55 (3F), -82 (46F), -87 (4F), -120 (2F), -124 (46F), -128 (22F), -131 (22F), -137 (11F), -139 (11F). The mean value of x is 11.

[0304] (Examples 3-7) 1.2 g of compound (1-3) was obtained in the same manner as in Example 1-8, except that compound (2-1) was replaced with 1 g of compound (2-3) obtained in Example 3-6.

[0305] [ka]

[0306] NMR spectra of compounds (1-3); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.6 (27H), 3.4 (2H), 1.3 (12H), 0.9 (6H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -55 (3F), -82 (46F), -87 (4F), -120 (2F), -124 (46F), -128 (22F), -131 (22F), -137 (11F), -139 (11F). The mean value of x is 11.

[0307] [Example 4] (Example 4-1) 394 g of CF2=CFOCF2CF2CF2CF2OCF=CF2 was placed in a 500 mL metal reactor and stirred at 180°C for 200 hours. The reactor temperature was reduced to 25°C, 55.6 g of compound (11-1) obtained in Example 1-1 was added, and the reactor was stirred at 180°C for 100 hours. The reactor temperature was reduced to 25°C, and the resulting crude reaction solution was purified by column chromatography to obtain 45.0 g of compound (4-13).

[0308] [ka]

[0309] NMR spectra of compounds (4-13); 1H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 4.0 (4H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -82 (40F), -85 (4F), -123 (4F), -124 (40F), -126 (4F), -128 (22F), -131 (22F), -137 (11F), -139 (11F). The mean value of x is 10.

[0310] (Example 4-2) Compound (4-14) was obtained in 22.8 g in the same manner as in Example 1-4, except that compound (4-1) was changed to 20 g of compound (4-13) obtained in Example 4-1, the amount of sodium fluoride powder was changed to 1.7 g, and the amount of CF3CF2CF2OCF(CF3)COF was changed to 14.8 g.

[0311] [ka]

[0312] NMR spectra of compounds (4-14); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 5.0 (4H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -79 (4F), -81 (6F), -82 (46F), -85 (4F), -119 (4F), -124 (40F), -126 (4F), -128 (22F), -129 (4F), -131 (24F), -137 (11F), -139 (11F). The mean value of x is 10.

[0313] (Example 4-3) Compound (4-15) was obtained in the same manner as in Example 1-5, except that compound (4-2) was replaced with 19.3 g of compound (4-14) obtained in Example 4-2, and the time of infusion of compound (4-14) into the CFE-419 solution was changed to 5 hours.

[0314] [ka]

[0315] NMR spectra of compounds (4-15); 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -79 (4F), -81 (6F), -82 (54F), -124 (48F), -128 (22F), -129 (4F), -131 (24F), -137 (11F), -139 (11F). The mean value of x is 10.

[0316] (Example 4-4) In a 50 mL round-bottom flask, 19.3 g of compound (4-15) obtained in Example 4-3, 1.6 g of sodium fluoride, and 20 mL of AC-2000 were placed and stirred in an ice bath. 1.2 g of methanol was added and stirred at 25°C for 1 hour. After filtration, the filtrate was purified by column chromatography. 13.5 g of compound (4-16) was obtained.

[0317] [ka]

[0318] NMR spectra of compounds (4-16); 1 1H-NMR (300.4 MHz, solvent: CDCl3, reference: TMS) δ (ppm): 4.2 (6H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -82 (44F), -119 (4F), -124 (44F), -128 (22F), -131 (22F), -137 (11F), -139 (11F). The mean value of x is 10.

[0319] (Examples 4-5) In a 50 mL round-bottom flask, 10.0 g of compound (4-16) obtained in Example 4-4, 1.5 g of H2NCH2C(CH2CH=CH2)3, and 10 mL of AC-2000 were placed and stirred at 0°C for 24 hours. The crude reaction solution was purified by column chromatography. 7.4 g of compound (2-4) was obtained.

[0320] [ka]

[0321] NMR spectra of compounds (2-4); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.1 (6H), 5.2 (12H), 3.4 (4H), 2.1 (12H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -82 (44F), -120 (4F), -124 (44F), -128 (22F), -131 (22F), -137 (11F), -139 (11F). The mean value of x is 10.

[0322] (Examples 4-6) 1.2 g of compound (1-4) was obtained in the same manner as in Example 1-8, except that compound (2-1) was replaced with 1 g of compound (2-4) obtained in Example 4-5.

[0323] [ka]

[0324] NMR spectra of compounds (1-4); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.6 (54H), 3.4 (4H), 1.3 (24H), 0.9 (12H). 19F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -82 (44F), -120 (4F), -124 (44F), -128 (22F), -131 (22F), -137 (11F), -139 (11F). The mean value of x is 10.

[0325] [Example 5] Compound (10-1) was obtained according to the method described in Example 11 of Patent Document 2. Mean value of x: 11.

[0326] [ka]

[0327] [Example 6] (Example 6-1) 16.2 g of HOCH2CF2CF2CH2OH and 13.8 g of potassium carbonate were placed in a 200 mL round-bottom flask and stirred at 120°C. 278 g of compound (11-1) obtained in Example 1-1 was added and stirred at 120°C for 2 hours. The temperature in the round-bottom flask was reduced to 25°C, 50 g each of AC-2000 and hydrochloric acid were added, and the mixture was separated to concentrate the organic phase. The resulting crude reaction solution was purified by column chromatography to obtain 117.7 g of compound (5-1).

[0328] [ka]

[0329] NMR spectrum of compound (5-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.0 (12H), 4.6 (20H), 4.2 (4H), 4.1 (4H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -85 (24F), -90 (24F), -120 (20F), -122 (4F), -123 (4F), -126 (24F), -144 (12F). The average value of x1 + x2 is 10.

[0330] (Example 6-2) Compound (5-2) was obtained in the same manner as in Example 1-4, except that compound (4-1) was replaced with 20 g of compound (5-1) obtained in Example 6-1, the amount of sodium fluoride powder was changed to 2.4 g, and the amount of CF3CF2CF2OCF(CF3)COF was changed to 18.8 g.

[0331] [ka]

[0332] NMR spectrum of compound (5-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.0 (12H), 5.0 (4H), 4.6 (20H), 4.2 (4H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -79 (4F), -81 (6F), -82 (6F), -85 (24F), -90 (24F), -119 (4F), -120 (20F), -122 (4F), -126 (24F), -129 (4F), -131 (2F), -144 (12F). The average value of x1 + x2 is 10.

[0333] (Example 6-3) Compound (5-3) was obtained in the same manner as in Example 1-5, except that compound (4-2) was replaced with 24 g of compound (5-2) obtained in Example 6-2, and the time of infusion of compound (5-2) into the CFE-419 solution was changed to 6 hours.

[0334] [ka]

[0335] NMR spectrum of compound (5-3); 19F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -79 (4F), -81 (6F), -82 (6F), -83 (52F), -87 (48F), -124 (52F), -129 (4F), -131 (2F). The mean value of x is 11.

[0336] (Example 6-4) In a 50 mL round-bottom flask, 25.3 g of compound (5-3) obtained in Example 6-3, 2.2 g of sodium fluoride, and 25 mL of AC-2000 were placed and stirred in an ice bath. 1.7 g of methanol was added and stirred at 25°C for 1 hour. After filtration, the filtrate was purified by column chromatography. 15 g of compound (5-4) was obtained.

[0337] [ka]

[0338] NMR spectra of compounds (5-4); 1 1H-NMR (300.4 MHz, solvent: CDCl3, reference: TMS) δ (ppm): 4.2 (6H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -83 (48F), -87 (48F), -119 (4F), -124 (48F). The mean value of x is 11.

[0339] (Example 6-5) In a 50 mL round-bottom flask, 15 g of compound (5-4) obtained in Example 6-4, 3.2 g of H2NCH2C(CH2CH=CH2)3, and 15 mL of AC-2000 were placed and stirred at 0°C for 24 hours. The crude reaction solution was purified by column chromatography. 11.2 g of compound (20-2) was obtained.

[0340] [ka]

[0341] NMR spectrum of compound (20-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.1 (6H), 5.2 (12H), 3.4 (4H), 2.1 (12H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -83 (48F), -87 (48F), -120 (4F), -124 (48F). The mean value of x is 11.

[0342] (Example 6-6) 1.2 g of compound (10-2) was obtained in the same manner as in Example 1-8, except that compound (2-1) was replaced with 1 g of compound (20-2) obtained in Example 6-5.

[0343] [ka]

[0344] NMR spectrum of compound (10-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.6 (54H), 3.4 (4H), 1.3 (24H), 0.9 (12H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -83 (48F), -87 (48F), -120 (4F), -124 (48F). The mean value of x is 11.

[0345] [Examples 7-13: Manufacturing and evaluation of goods] The compounds obtained in Examples 1-6, and the compounds obtained in Examples 1 and 5 (compound (1-1) and compound (10-1)) were mixed in a mass ratio of 1:1 to form a composition used to surface-treat a substrate to obtain the articles of Examples 7-13. For each example, the following dry coating method and wet coating method were used as the surface treatment method. Chemically strengthened glass was used as the substrate. The obtained articles were evaluated by the following method. The results are shown in Table 1.

[0346] (Dry coating method) Dry coating was performed using a vacuum deposition apparatus (ULVAC, VTR350M) (vacuum deposition method). 0.5 g of each compound obtained in Examples 1-6 was packed into a molybdenum boat inside the vacuum deposition apparatus, and the inside of the vacuum deposition apparatus was filled to 1 × 10⁻⁶ -3 The air was evacuated to below Pa. The boat containing the compound was heated at a heating rate of 10°C / min or less, and when the deposition rate measured by a quartz crystal film thickness gauge exceeded 1 nm / second, the shutter was opened to begin film formation on the substrate surface. When the film thickness reached approximately 50 nm, the shutter was closed to end film formation on the substrate surface. The substrate on which the compound was deposited was heat-treated at 200°C for 30 minutes and washed with dichloropentafluoropropane (AGC, AK-225) to obtain an article with a surface layer on the substrate surface.

[0347] (Wet coating method) Each compound obtained in Examples 1-6 was mixed with C4F9OC2H5 (Novec® 7200, manufactured by 3M) as a medium to prepare a coating solution with a solid content of 0.05%. The substrate was dipped into the coating solution and left for 30 minutes before being removed (dip coating method). The coating film was dried at 200°C for 30 minutes and washed with AK-225 to obtain an article having a surface layer on the surface of the substrate.

[0348] (Evaluation method) <Method for measuring contact angle> The contact angle of approximately 2 μL of distilled water or n-hexadecane placed on the surface of the surface layer was measured using a contact angle measuring device (Kyowa Interface Science Co., Ltd., DM-500). Measurements were taken at five different locations on the surface of the surface layer, and the average value was calculated. The 2θ method was used to calculate the contact angle.

[0349] <Initial contact angle> The initial water contact angle and initial n-hexadecane contact angle of the surface layer were measured using the measurement method described above. The evaluation criteria are as follows. Initial water contact angle: ◎ (Excellent): 115 degrees or higher. ○ (Good): 110 degrees or higher and less than 115 degrees. △ (Acceptable): 100 degrees or more and less than 110 degrees. × (Not allowed): Below 100 degrees. Initial n-hexadecane contact angle: ◎ (Excellent): 66 degrees or higher. ○ (Good): 65 degrees or higher and less than 66 degrees. △ (Acceptable): 63 degrees or higher and less than 65 degrees. × (Not allowed): Below 63 degrees.

[0350] <Lightfastness> The surface layer was subjected to a tabletop xenon arc lamp type accelerated lightfastness tester (SUNTEST XLS+, manufactured by Toyo Seiki Co., Ltd.) at a black panel temperature of 63°C, using a light source (650W / m²). 2 After irradiating with light (300-700 nm) for 1,000 hours, the water contact angle was measured. A smaller decrease in the water contact angle after accelerated lightfastness testing indicates less performance degradation due to light and superior lightfastness. The evaluation criteria are as follows: ◎(Excellent): Change in water contact angle after accelerated lightfastness test is 2 degrees or less. ○ (Good): The change in water contact angle after accelerated lightfastness testing is greater than 2 degrees and less than or equal to 5 degrees. △ (Acceptable): The change in water contact angle after accelerated lightfastness testing is greater than 5 degrees and less than or equal to 10 degrees. × (Not acceptable): Change in water contact angle after accelerated lightfastness test exceeds 10 degrees.

[0351] <Abrasion resistance (steel wool)> For the surface layer, a reciprocating traverse tester (manufactured by KNT Co., Ltd.) was used in accordance with JIS L0849:2013 (ISO 105-X12:2001). Steel wool bonstar (#0000) was reciprocated 15,000 times at a pressure of 98.07 kPa and a speed of 320 cm / min, and then the water contact angle was measured using the method described above. The smaller the decrease in water repellency (water contact angle) after friction, the smaller the decrease in performance due to friction and the better the abrasion resistance. The evaluation criteria are as follows. ◎(Excellent): The change in water contact angle after 15,000 cycles is 2 degrees or less. ○ (Good): The change in water contact angle after 15,000 cycles is greater than 2 degrees and less than or equal to 5 degrees. △ (Acceptable): The change in water contact angle after 15,000 cycles is greater than 5 degrees and less than or equal to 10 degrees. × (Not acceptable): The change in water contact angle after 15,000 cycles exceeds 10 degrees.

[0352] <Chemical resistance (alkali resistance)> The articles were immersed in a 1N sodium hydroxide aqueous solution (pH=14) for 5 hours, then rinsed with water, air-dried, and the water contact angle was measured using the method described above. A smaller decrease in the water contact angle after the test indicates less performance degradation due to alkali and superior alkali resistance. The evaluation criteria are as follows. ◎(Excellent): Change in water contact angle after alkali resistance test is 2 degrees or less. ○ (Good): The change in water contact angle after alkali resistance testing is greater than 2 degrees and less than or equal to 5 degrees. △ (Acceptable): The change in water contact angle after alkali resistance testing is greater than 5 degrees and less than or equal to 10 degrees. × (Unacceptable): Change in water contact angle after alkali resistance test exceeds 10 degrees.

[0353] <Chemical resistance (saltwater resistance)> A salt spray test was conducted in accordance with JIS H8502. Specifically, the product was exposed to a salt spray atmosphere for 300 hours in a salt spray tester (manufactured by Suga Test Instruments Co., Ltd.), and then the water contact angle was measured using the method described above. The smaller the decrease in the water contact angle after the test, the less the performance degradation due to salt water and the better the salt water resistance. The evaluation criteria are as follows. ◎(Excellent): The change in water contact angle after the salt spray test is 2 degrees or less. ○ (Good): The change in water contact angle after the salt spray test is greater than 2 degrees and less than or equal to 5 degrees. △ (Acceptable): The change in water contact angle after the salt spray test is greater than 5 degrees and less than or equal to 10 degrees. × (Unacceptable): Change in water contact angle after salt spray test exceeds 10 degrees.

[0354] <Slip resistance> The coefficient of dynamic friction of the surface layer of artificial skin (Idemitsu Technofine, PBZ13001) was measured using a load-variable friction and wear testing system (Shinto Kagaku Co., Ltd., HHS2000) under the conditions of a contact area of ​​3 cm × 3 cm and a load of 0.98 N. A higher coefficient of dynamic friction indicates better slip resistance. The evaluation criteria are as follows. ◎(Excellent): The coefficient of kinetic friction is 0.6 or higher. ○ (Good): The coefficient of kinetic friction is 0.5 or higher and less than 0.6. △ (Acceptable): The coefficient of kinetic friction is 0.4 or higher and less than 0.5. × (Not acceptable): The coefficient of kinetic friction is less than 0.4.

[0355] <Fingerprint stain removal> An artificial fingerprint solution (a solution consisting of oleic acid and squalene) was applied to the flat surface of a silicone rubber stopper. Excess oil was then wiped off with a nonwoven fabric (Asahi Kasei Corporation, Bencot® M-3) to prepare a fingerprint stamp. The fingerprint stamp was placed on the surface layer and pressed down with a load of 9.8 N for 10 seconds. The haze at the fingerprint site was measured with a haze meter and set as the initial value. The fingerprint site was wiped with a reciprocating traverse tester (KNT Corporation) equipped with tissue paper, under a load of 4.9 N. The haze value was measured after each reciprocating wipe, and the number of wipes required to reduce the haze to 10% or less of the initial value was determined. Fewer wipes indicate easier removal of fingerprint stains and superior fingerprint stain removal performance. The evaluation criteria are as follows. ◎(Excellent): Wiping required 3 times or less. ○ (Good): Wipeable 4-5 times. △ (Acceptable): Wipes 6-8 times. × (Not allowed): Wiping more than 9 times.

[0356] [Table 1]

[0357] Examples 7-10 using this compound confirmed excellent initial water and oil repellency, light resistance, abrasion resistance, chemical resistance, slip resistance, and fingerprint stain removal properties. Examples 11 and 12, which used conventional fluorine-containing ether compounds, exhibited poor friction resistance, lubricity, light resistance, and chemical resistance. On the other hand, in Example 13, which used the present composition combining this compound with a conventional fluorine-containing ether compound, slip resistance and chemical resistance were improved compared to Example 11, demonstrating the full effectiveness of this compound.

[0358] Furthermore, various fluorine-containing ether compounds (including this compound) were synthesized. Examples of synthesis are shown below. [Example 14] (Example 14-1) 20 g of compound (11-1) obtained in Example 1-1 was placed in a 100 mL metal reactor, and 19.1 g of CF2=CFOCF2CF2CF3 was added. The mixture was stirred at 180 °C for 300 hours. The resulting organic phase was concentrated and purified by distillation to obtain 5.9 g of compound (33-1).

[0359] [ka]

[0360] NMR spectrum of compound (33-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 4.1 (2H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -81 (3F), -82 (4F), -123 (2F), -126 (2F), -128 (4F), -129 (2F), -137 (2F).

[0361] (Example 14-2) Compound (33-2) was obtained in the same manner as in Example 1-3, except that compound (23-1) was replaced with 4.9 g of compound (33-1) obtained in Example 14-1, and potassium carbonate was changed to 0.5 g.

[0362] [ka]

[0363] NMR spectrum of compound (33-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.0 (10H), 4.6 (20H), 4.1 (2H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -81 (3F), -82 (24F), -90 (20F), -120 (20F), -123 (2F), -126 (22F), -128 (4F), -129 (2F), -137 (2F), -144 (10F). The average value for n+1 is 10.

[0364] (Example 14-3) Compound (33-3) was obtained in the same manner as in Example 1-4, except that compound (4-1) was replaced with 10 g of compound (33-2) obtained in Example 14-2, the amount of sodium fluoride powder was changed to 0.6 g, and the amount of CF3CF2CF2OCF(CF3)COF was changed to 5 g.

[0365] [ka]

[0366] NMR spectrum of compound (33-3); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.0 (10H), 5.0 (2H), 4.6 (20H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -81 (6F), -82 (26F), -83 (3F), -90 (20F), -119 (2F), -120 (20F), -126 (22F), -128 (4F), -129 (4F), -132 (1F), -137 (2F), -144 (10F). The average value for n+1 is 10.

[0367] (Example 14-4) 12 g of compound (33-4) was obtained in the same manner as in Example 1-5, except that compound (4-2) was replaced with 10 g of compound (33-3) obtained in Example 14-3.

[0368] [ka]

[0369] NMR spectrum of compound (33-4); 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -81 (6F), -82 (6F), -83 (3F), -84 (42F), -90 (40F), 124 (44F), -128 (4F), -129 (4F), -132 (1F), -137 (2F). The average value for n+1 is 10.

[0370] (Example 14-5) 11 g of compound (33-5) was obtained in the same manner as in Example 1-6, except that compound (4-3) was replaced with 12 g of compound (33-4) obtained in Example 14-4.

[0371] [ka]

[0372] NMR spectrum of compound (33-5); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 4.2 (3H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -81 (3F), -82 (4F), -84 (40F), -90 (40F), -118 (2F), 124 (42F), -128 (4F), -129 (2F), -137 (2F). The average value of n is 9.

[0373] (Example 14-6) Compound (33-6) was obtained in the same manner as in Example 1-7, except that compound (4-4) was replaced with 12 g of compound (33-5) obtained in Example 14-5.

[0374] [ka]

[0375] NMR spectrum of compound (33-6); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.1 (3H), 5.2 (6H), 3.4 (2H), 2.1 (6H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -81 (3F), -82 (4F), -84 (40F), -90 (40F), -120 (2F), 124 (42F), -128 (4F), -129 (2F), -137 (2F). The average value of n is 9.

[0376] (Example 14-7) 1.1 g of compound (33-7) was obtained in the same manner as in Example 1-8, except that compound (2-1) was replaced with 1 g of compound (33-6) obtained in Example 14-6.

[0377] [ka]

[0378] NMR spectrum of compound (33-7); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.6 (27), 3.4 (2H), 1.3 (12H), 0.9 (6H). 19F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -81 (3F), -82 (4F), -84 (40F), -90 (40F), -120 (2F), 124 (42F), -128 (4F), -129 (2F), -137 (2F). The average value of n is 9.

[0379] [Example 15] (Example 15-1) In a 50 mL round-bottom flask, 10 g of compound (33-1) obtained in Example 14-1, 15.6 g of trifluoromethanesulfonic anhydride, 5.6 g of triethylamine, and 10 g of 1,3-bistrifluoromethylbenzene were mixed and reacted at 40°C for 3 hours. After the reaction, the crude solution was washed with water and the organic layer was recovered. The solvent and other substances were removed by distillation under reduced pressure to obtain 9.9 g of compound (34-1).

[0380] [ka] However, OTf in the formula represents ―OSO2CF3.

[0381] NMR spectrum of compound (34-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 5.0 (2H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -74 (3F), -81 (3F), -82 (4F), -119 (2F), -126 (2F), -128 (4F), -129 (2F), -137 (2F).

[0382] (Example 15-2) In a 50 mL round-bottom flask, 10 g of compound (34-1) obtained in Example 15-1, 13.1 g of cesium carbonate, 59 g of 1,3-bistrifluoromethylbenzene, and 59 g of FLUOROLINK (trademark registered) D4000 from Solvay Solexis were mixed and reacted at 80°C for 6 hours. The crude solution after the reaction was washed with aqueous hydrochloric acid and the organic layer was recovered. The solvent and other substances were removed by reduced pressure distillation, and the compound (34-2) was purified by column chromatography to obtain 20 g. Furthermore, in the following compounds (34-2) to (34-7), -[CF2O] C1 -[CF2CF2O] C2 The dash (-) represents a random copolymer chain of one carbon atom (CF2O) and two carbon atoms (CF2CF2O).

[0383] [ka]

[0384] NMR spectrum of compound (34-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 5.0 (2H), 4.2 (2H), 3.9 (2H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -55 (44F), -80 (2F), -81 (5F), -82 (4F), -90 (96F), -119 (2F), -126 (2F), -128 (4F), -129 (2F), -137 (2F). Average value for C1: 22. Average value for C2: 24.

[0385] (Example 15-3) Compound (34-3) was obtained in the same manner as in Example 1-5, except that compound (4-2) was replaced with 20 g of compound (34-2) obtained in Example 15-2.

[0386] [ka]

[0387] NMR spectrum of compound (34-3); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 5.0 (2H), 4.7 (2H), 4.2 (2H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -55 (44F), -80 (2F), -81 (8F), -82 (6F), -83 (3F), -90 (96F), -119 (2F), -126 (2F), -128 (4F), -129 (4F), -132 (1F), -137 (2F). Average value for C1: 22. Average value for C2: 24.

[0388] (Example 15-4) Compound (34-4) was obtained in the same manner as in Example 1-5, except that compound (4-2) was replaced with 12 g of compound (34-3) obtained in Example 15-3.

[0389] [ka]

[0390] NMR spectrum of compound (34-4); 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -55 (44F), -81 (6F), -82 (8F), -83 (3F), -90 (104F), -124 (4F), -128 (4F), -129 (4F), -132 (1F), -137 (2F). Average value for C1: 22. Average value for C2: 24.

[0391] (Example 15-5) 19 g of compound (34-5) was obtained in the same manner as in Example 1-6, except that compound (4-3) was replaced with 20 g of compound (34-4) obtained in Example 15-4.

[0392] [ka]

[0393] NMR spectra of compounds (34-5); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 4.2 (3H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -55 (44F), -80 (2F), -81 (3F), -82 (6F), -90 (100F), -124 (4F), -128 (4F), -129 (2F), -137 (2F). Average value for C1: 22. Average value for C2: 24.

[0394] (Example 15-6) 15 g of compound (34-6) was obtained in the same manner as in Example 1-7, except that compound (4-4) was replaced with 19 g of compound (34-5) obtained in Example 15-5.

[0395] [ka]

[0396] NMR spectra of compounds (34-6); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.1 (3H), 5.2 (6H), 3.4 (2H), 2.1 (6H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -55 (44F), -79 (2F), -81 (3F), -82 (6F), -90 (100F), -124 (4F), -128 (4F), -129 (2F), -137 (2F). Average value for C1: 22. Average value for C2: 24.

[0397] (Example 15-7) 1.1 g of compound (34-7) was obtained in the same manner as in Example 1-8, except that compound (2-1) was replaced with 1 g of compound (34-6) obtained in Example 15-6.

[0398] [ka]

[0399] NMR spectra of compounds (34-7); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.6 (27), 3.4 (2H), 1.3 (12H), 0.9 (6H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -55 (44F), -79 (2F), -81 (3F), -82 (6F), -90 (100F), -124 (4F), -128 (4F), -129 (2F), -137 (2F). Average value for C1: 22. Average value for C2: 24.

[0400] [Example 16] (Example 16-1) In a 200 mL round-bottom flask, 10.0 g of 1,4-cyclohexanedimethanol and 19.2 g of potassium carbonate were added and stirred at 120°C. 192.8 g of compound (11-1) obtained in Example 1-1 was added and the mixture was stirred at 120°C for 2 hours. The temperature in the round-bottom flask was reduced to 25°C, 100 g each of AC-2000 and hydrochloric acid were added, and the mixture was separated to concentrate the organic phase. The resulting crude reaction solution was purified by column chromatography to obtain 96.6 g of compound (35-1).

[0401] [ka]

[0402] NMR spectrum of compound (35-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.0 (10H), 4.6 (16H), 4.1 (4H), 3.3 (4H), 1.9 (2H), 1,5 (8H). 19F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -82 (20F), -90 (20F), -120 (16F), -123 (4F), -126 (20F), -144 (10F). The mean of (m+1)+(n+1) is 10.

[0403] (Example 16-2) 100.8 g of compound (35-2) was obtained in the same manner as in Example 1-4, except that compound (4-1) was replaced with 90 g of compound (35-1) obtained in Example 16-1, the amount of sodium fluoride powder was changed to 5.4 g, and the amount of CF3CF2CF2OCF(CF3)COF was changed to 85.8 g.

[0404] [ka]

[0405] NMR spectrum of compound (35-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.0 (10H), 5.0 (4H), 4.6 (16H), 3.3 (4H), 1.9 (2H), 1,5 (8H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -81 (6F), -82 (24F), -83 (6F), -90 (20F), -119 (4F), -120 (16F), -126 (20F), -129 (4F), -132 (2F), -144 (10F). The mean of (m+1)+(n+1) is 10.

[0406] (Example 16-3) Compound (35-3) was obtained in the same manner as in Example 1-5, except that compound (4-2) was replaced with 40 g of compound (35-2) obtained in Example 16-2, and the time of infusion of compound (35-2) into the CFE-419 solution was changed to 8 hours.

[0407] [ka]

[0408] NMR spectrum of compound (35-3); 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -81 (6F), -82 (4F), -83 (6F), -84 (40F), -90 (40F), -93 (4F), -124 (40F), -127 (8F), -129 (4F), -132 (2F), -184 (2F). The mean of (m+1)+(n+1) is 10.

[0409] (Example 16-4) In a 50 mL round-bottom flask, 40.0 g of compound (35-3) obtained in Example 16-3, 3.4 g of sodium fluoride, and 40 mL of AC-2000 were placed and stirred in an ice bath. 2.6 g of methanol was added and the mixture was stirred at 25°C for 1 hour. After filtration, the filtrate was purified by column chromatography. 31.3 g of compound (35-4) was obtained.

[0410] [ka]

[0411] NMR spectrum of compound (35-4); 1 1H-NMR (300.4 MHz, solvent: CDCl3, reference: TMS) δ (ppm): 4.2 (6H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -84 (36F), -90 (40F), -93 (4F), -118 (4F), -124 (36F), -127 (8F), -184 (2F). The average value of m+n is 8.

[0412] (Example 16-5) In a 50 mL round-bottom flask, 20 g of compound (35-4) obtained in Example 16-4, 2.3 g of H2NCH2C(CH2CH=CH2)3, and 15 mL of AC-2000 were placed and stirred at 0°C for 24 hours. The crude reaction solution was purified by column chromatography. 12.7 g of compound (35-5) was obtained.

[0413] [ka]

[0414] NMR spectrum of compound (35-5); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 6.1 (6H), 5.2 (12H), 3.4 (4H), 2.1 (12H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -84 (36F), -90 (40F), -93 (4F), -120 (4F), -124 (36F), -127 (8F), -184 (2F). The average value of m+n is 8.

[0415] (Example 16-6) 1.1 g of compound (35-6) was obtained in the same manner as in Example 1-8, except that compound (2-1) was replaced with 1 g of compound (35-5) obtained in Example 16-5.

[0416] [ka]

[0417] NMR spectra of compounds (35-6); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.6 (54H), 3.4 (4H), 1.3 (24H), 0.9 (12H). 19F-NMR (282.7 MHz, solvent: CDCl3, reference: CFCl3) δ (ppm): -84 (36F), -90 (40F), -93 (4F), -120 (4F), -124 (36F), -127 (8F), -184 (2F). The average value of m+n is 8. [Industrial applicability]

[0418] The fluorine-containing ether compound of the present invention can be used in various applications where lubrication and water / oil repellency are required. For example, it can be used in display input devices such as touch panels, surface protective coatings for transparent glass or transparent plastic components, anti-fouling coatings for kitchens, water-repellent and moisture-proof coatings and anti-fouling coatings for electronic devices, heat exchangers, batteries, etc., anti-fouling coatings for toiletries, coatings for components that require both conductivity and liquid repellency, water-repellent, waterproof and water-slip coatings for heat exchangers, and low-friction surface coatings for vibrating screens and the inside of cylinders. More specific examples of use include front protective plates, anti-reflective plates, polarizing plates, anti-glare plates for displays, or those with anti-reflective coatings applied to their surfaces; touch panel sheets and touch panel displays for mobile phones and personal digital assistants, and other devices with display input devices that allow users to operate the screen with their fingers or palms; decorative building materials for wet areas such as toilets, bathrooms, washrooms, and kitchens; waterproof coatings for wiring boards; water-repellent and waterproof coatings for heat exchangers; water-repellent coatings for solar cells; waterproof and water-repellent coatings for printed circuit boards; waterproof and water-repellent coatings for electronic equipment casings and electronic components; insulation-enhancing coatings for power transmission lines; waterproof and water-repellent coatings for various filters; waterproof coatings for radio wave absorbing materials and sound-absorbing materials; stain-resistant coatings for baths, kitchen equipment, and toiletries; water-repellent, waterproof, and water-slip coatings for heat exchangers; low-friction surface coatings for vibrating screens and cylinder interiors; and surface protection coatings for machine parts, vacuum equipment parts, bearing parts, automobile parts, tools, etc. Furthermore, the entire contents of the specifications, claims, and abstracts of Japanese Patent Application No. 2019-022079, filed on February 8, 2019, and Japanese Patent Application No. 2019-220995, filed on December 6, 2019, are incorporated herein by reference as disclosures of the present invention.

Claims

1. A fluorine-containing ether compound, represented by the formula (1A) below. [R ｆ -] ａ１ Q １ [-T] ｂ１ (1A) however, R ｆ This is a group represented by the following formula (g1a), R ｆ１ -(OR ｆ２ ) ｍ (OR ｆ３ ) ｎ - (g1a) Q １ This is a single bond or a1+b1 valent linking group, T is -Si(R) ３－ｃ (L) ｃ And, R is an alkyl group, L is a hydrolyzable group or a hydroxyl group, and the two or more Ls in T may be the same or different. a1 is an integer greater than or equal to 1, b1 is an integer greater than or equal to 1, c is 2 or 3, If there are two or more T's, the two or more T's may be the same or different. R ｆ１ This is a fluoroalkyl group having 1 to 20 carbon atoms, or a monovalent fluorinated hydrocarbon group having a fluorine-containing ring structure, wherein the monovalent fluorinated hydrocarbon group having a fluorine-containing ring structure is one of the groups in the following formula (where * indicates a bond): 【Chemistry 1】 R ｆ２ This is a fluoroalkylene group having 1 to 6 carbon atoms (however, Q １ R that binds ｆ２ Q １ At least one fluorine atom is bonded to the carbon atom at the terminal end of the side. R ｆ３ This refers to a divalent fluorinated hydrocarbon group having a fluorine-containing ring structure (however, Q １ R that binds ｆ３ Q １ At least one fluorine atom is bonded to the carbon atom at the terminal end of the side. OR ｆ３ is one of the bases in the following equations (where * indicates a bond): 【Chemistry 2】 n is R ｆ１ If it has a fluorine-containing ring structure, it is an integer from 0 to 500, R ｆ１ If it does not have a fluorine-containing ring structure, it is an integer from 1 to 500, and if n is 2 or more, (OR ｆ３ ) ｎ is two or more OR ｆ３ It may consist of, When n is 0, m is an integer between 5 and 500. When n is 1 or greater, m is an integer between 2 and 500. If m is 2 or greater, (OR ｆ２ ) ｍ is two or more OR ｆ２ It may consist of, m pieces (OR ｆ２ ) and n (OR ｆ３ The order of joining the elements is not restricted.

2. A fluorine-containing ether compound, represented by the formula (1A) below. [R ｆ -] ａ１ Q １ [-T] ｂ１ (1A) however, R ｆ It has a first substructure represented by the following formula (1) and a second substructure represented by the following formula (2), Furthermore, it is a monovalent polyfluoropolyether chain having five or more of the first substructure or two or more of the second substructure, with carbon atoms at the bonding ends, R ｆ If there are two or more, then there are two or more R ｆ They may be the same or different. -OR ｆ１２ - (1) -OR ｆ１３ - (2) R ｆ１２ This is a fluoroalkylene group having 1 to 6 carbon atoms. R ｆ１３ This is a group having a fluorine-containing ring structure which may have heteroatoms, OR ｆ１３ is one of the bases in the following equations (where * indicates a bond): 【Transformation 3】 Q １ This is a group represented by formula (g2-1) (where a1 = d1 + d3 and b1 = d2 + d4), a group represented by formula (g2-2) (where a1 = e1 and b1 = e2), a group represented by formula (g2-3) (where a1 = 1 and b1 = 2), a group represented by formula (g2-4) (where a1 = h1 and b1 = h2), a group represented by formula (g2-5) (where a1 = i1 and b1 = i2), a group represented by formula (g2-6) (where a1 = 1 and b1 = 1), or a group represented by formula (g2-7) (where a1 = 1 and b1 = i3 + 1), T is -Si(R) ３－ｃ (L) ｃ And, R is an alkyl group, L is a hydrolyzable group or a hydroxyl group, and the two or more Ls in T may be the same or different. a1 is an integer greater than or equal to 1, b1 is an integer greater than or equal to 1, c is 2 or 3, If there are two or more T's, the two or more T's may be the same or different. 【Chemistry 4】 (-A-Q １２ -) ｅ１ C(R ２ ) ４－ｅ１－ｅ２ (-Q ２２ -) ｅ２ (g2-2) -A-Q １３ -N(-Q ２３ -) ２ (g2-3) (-A-Q １４ -) ｈ１ Z(-Q ２４ -) ｈ２ (g2-4) (-A-Q １５ -) ｉ１ Si(R ３ ) ４－ｉ１－ｉ２ (-Q ２５ -) ｉ２ (g2-5) -A-Q ２６ - (g2-6) -A-Q １２ -CH(-Q ２２ -)-Si(R ３ ) ３－ｉ３ (-Q ２５ -) ｉ３ (g2-7) however, In equations (g2-1) to (g2-7), side A is R ｆ Connect to Q ２２ Q ２３ Q ２４ Q ２５ and Q ２６ The side is connected to T, A is a single bond, -C(O)NR ６ -, -C(O)-, -OC(O)O-, -NHC(O)O-, -NHC(O)NR ６ -, -O-, or -SO ２ NR ６ - and Q １１ This refers to a single bond, -O-, an alkylene group, or an alkylene group with two or more carbon atoms with -C(O)NR between carbon atoms. ６ -, -C(O)-, -NR ６ A group having - or -O-, Q １２ is a single bond, an alkylene group, or a group having -C(O)NR ６ -, -C(O)-, -NR ６ -, or -O-, and when Q １ has two or more Q １２ , the two or more Q １２ may be the same or different, Q １３ This includes single bonds (where A is -C(O)-), alkylene groups, and -C(O)NR between carbon atoms of alkylene groups with 2 or more carbon atoms. ６ -, -C(O)-, -NR ６ A group having - or -O-, or a group having -C(O)- at the N-side terminal of an alkylene group, Q １４ is such that when the atom in Z to which Q １４ is attached is a carbon atom, Q １２ is, and when the atom in Z to which Q １４ is attached is a nitrogen atom, Q １３ is, and when Q １ has two or more Q １４ , the two or more Q １４ may be the same or different, Q １５ This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between carbon atoms. ６ -, -C(O)-, -NR ６ A group having - or -O-, Q １ Q １５ If you have two or more Q １５ They may be the same or different. Q ２２ This refers to an alkylene group, an alkylene group with 2 or more carbon atoms, with -C(O)NR between the carbon atoms. ６ -, -C(O)-, -NR ６ A group having - or -O-, or -C(O)NR at the non-T-connected end of an alkylene group. ６ -, -C(O)-, -NR ６ A group having - or -O-, or an alkylene group having 2 or more carbon atoms with -C(O)NR between carbon atoms. ６ -, -C(O)-, -NR ６ - or -O- and -C(O)NR at the end not connected to T ６ -, -C(O)-, -NR ６ A group having - or -O-, Q １ Q ２２ If you have two or more Q ２２ They may be the same or different. Q ２３ This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between carbon atoms. ６ -, -C(O)-, -NR ６ A group having - or -O-, and two Q ２３ They may be the same or different. Q ２４ Q ２４ If the atom at Z to which it is bonded is a carbon atom, then Q ２２ Q ２４ If the atom at Z to which the bond is formed is a nitrogen atom, then Q ２３ Q １ Q ２４ If you have two or more Q ２４ They may be the same or different. Q ２５ This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between carbon atoms. ６ -, -C(O)-, -NR ６ A group having - or -O-, Q １ Q ２５ If you have two or more Q ２５ They may be the same or different. Q ２６ This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between carbon atoms. ６ -, -C(O)-, -NR ６ A group having - or -O-, Z is Q １４ It has a carbon or nitrogen atom that is directly bonded to it and Q ２４ It is a group having an a1+b1 valent ring structure with a carbon or nitrogen atom to which it is directly bonded, R １ Q is a hydrogen atom or an alkyl group, １ R １ If there are two or more, then there are two or more R １ They may be the same or different. R ２ is a hydrogen atom, a hydroxyl group, an alkyl group, or an acyloxy group. R ３ It is an alkyl group, R ６ These are a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. d1 is an integer between 0 and 3, d2 is an integer between 0 and 3, and d1 + d2 is an integer between 1 and 3. d3 is an integer between 0 and 3, d4 is an integer between 0 and 3, and d3 + d4 is an integer between 1 and 3. d1 + d3 is Q １ In this case, it is an integer from 1 to 5. d2 + d4 is Q １ In this case, it is an integer from 1 to 5. e1 + e2 is either 3 or 4. e1 is Q １ In this case, it is an integer from 1 to 3, e2 is Q １ In this case, it is an integer from 1 to 3, h1 is Q １ In this case, it is an integer greater than or equal to 1, h2 is an integer greater than or equal to 1, i1 + i2 is either 3 or 4. i1 is Q １ In this case, it is an integer from 1 to 3, i2 is Q １ In this case, it is an integer from 1 to 3, i3 is either 2 or 3.

3. A fluorine-containing ether compound, represented by the formula (1A) below. [R ｆ -] ａ１ Q １ [-T] ｂ１ (1A) however, R ｆ This is a group represented by the following formula (g1a), R ｆ１ -(OR ｆ２ ) ｍ (OR ｆ３ ) ｎ - (g1a) Q １ This is a linked group with a1+b1 valency, Tは、-Ar、-OR １０ 、-SR １０ 、-NOR １０ 、-C(=O)R １０ 、-N(R １０ ) ２ 、-N ＋ (R １０ ) ３ X ３ 、-C≡N、-C(=NR １０ )-R １０ 、-N ＋ ≡N、-N=NR １０ 、-C(=O)OR １０ 、-C(=O)OX ２ 、-C(=O)OX ４ 、-C(=O)OC(=O)R １０ 、-SO ２ R １０ 、-SO ３ H、-SO ３ X ２ 、-O-P(=O)(-OR １０ ) ２ 、-O-P(=O)(-OR １０ )(-OX ２ )、-N=C=O、-Si(R) ３－ｃ (L) ｃ 、-C(R １０ )=C(R １０ ) ２ 、-C≡C(R １０ )、-C(=O)N(R １０ ) ２ 、-N(R １０ )C(=O)R １０ 、-Si(R １０ ) ２ -O-Si(R １０ ) ３ 、-NH-C(=O)R １０ 、-C(=O)NHR １０ 、-I、 【Transformation 5】 R １０ R is a hydrogen atom, a C1-C6 alkyl group or fluoroalkyl group, or an aryl group which may have a substituent. １０ If there are two or more, then there are two or more R １０ They may be the same or different from each other. Ar is an aryl group which may have substituents. X ２ These are alkali metal ions or ammonium ions, X ３ It is a halide ion, X ４ It is a halogen atom, R is an alkyl group, L is a hydrolyzable group or a hydroxyl group, and the two or more Ls in T may be the same or different. a1 is an integer greater than or equal to 1, b1 is an integer greater than or equal to 2, c is 2 or 3, Two or more Ts may be the same or different. R ｆ１ This is a fluoroalkyl group having 1 to 20 carbon atoms, or a monovalent fluorinated hydrocarbon group having a fluorine-containing ring structure, wherein the monovalent fluorinated hydrocarbon group having a fluorine-containing ring structure is one of the groups in the following formula (where * indicates a bond): 【Transformation 6】 R ｆ２ This is a fluoroalkylene group having 1 to 6 carbon atoms (however, Q １ R that binds ｆ２ Q １ At least one fluorine atom is bonded to the carbon atom at the terminal end of the side. R ｆ３ This refers to a divalent fluorinated hydrocarbon group having a fluorine-containing ring structure (however, Q １ R that binds ｆ３ Q １ At least one fluorine atom is bonded to the carbon atom at the terminal end of the side. OR ｆ３ is one of the bases in the following equations (where * indicates a bond): 【Transformation 7】 n is R ｆ１ If it has a fluorine-containing ring structure, it is an integer from 0 to 500, R ｆ１ If it does not have a fluorine-containing ring structure, it is an integer from 1 to 500, and if n is 2 or more, (OR ｆ３ ) ｎ is two or more OR ｆ３ It may consist of, When n is 0, m is an integer between 5 and 500. When n is 1 or greater, m is an integer between 2 and 500. If m is 2 or greater, (OR ｆ２ ) ｍ is two or more OR ｆ２ It may consist of, m pieces (OR ｆ２ ) and n (OR ｆ３ The order of joining the elements is not restricted.

4. A fluorine-containing ether compound, represented by the formula (1A) below. [R ｆ -] ａ１ Q １ [-T] ｂ１ (1A) however, R ｆ It has a first substructure represented by the following formula (1) and a second substructure represented by the following formula (2), Furthermore, it is a monovalent polyfluoropolyether chain having five or more of the first substructure or two or more of the second substructure, with carbon atoms at the bonding ends, R ｆ If there are two or more, then there are two or more R ｆ They may be the same or different. -OR ｆ１２ - (1) -OR ｆ１３ - (2) R ｆ１２ This is a fluoroalkylene group having 1 to 6 carbon atoms. R ｆ１３ This is a group having a fluorine-containing ring structure which may have heteroatoms, OR ｆ１３ is one of the bases in the following equations (where * indicates a bond): 【Transformation 8】 Q １ This is a group represented by formula (g2-1) (where a1 = d1 + d3 and b1 = d2 + d4), a group represented by formula (g2-2) (where a1 = e1 and b1 = e2), a group represented by formula (g2-3) (where a1 = 1 and b1 = 2), a group represented by formula (g2-4) (where a1 = h1 and b1 = h2), a group represented by formula (g2-5) (where a1 = i1 and b1 = i2), or a group represented by formula (g2-7) (where a1 = 1 and b1 = i3 + 1), Tは、-Ar、-OR １０ 、-SR １０ 、-NOR １０ 、-C(=O)R １０ 、-N(R １０ ) ２ 、-N ＋ (R １０ ) ３ X ３ 、-C≡N、-C(=NR １０ )-R １０ 、-N ＋ ≡N、-N=NR １０ 、-C(=O)OR １０ 、-C(=O)OX ２ 、-C(=O)OX ４ 、-C(=O)OC(=O)R １０ 、-SO ２ R １０ 、-SO ３ H、-SO ３ X ２ 、-O-P(=O)(-OR １０ ) ２ 、-O-P(=O)(-OR １０ )(-OX ２ )、-N=C=O、-Si(R) ３－ｃ (L) ｃ 、-C(R １０ )=C(R １０ ) ２ 、-C≡C(R １０ )、-C(=O)N(R １０ ) ２ 、-N(R １０ )C(=O)R １０ 、-Si(R １０ ) ２ -O-Si(R １０ ) ３ 、-NH-C(=O)R １０ 、-C(=O)NHR １０ 、-I、 【Chemistry 9】 R １０ R is a hydrogen atom, a C1-C6 alkyl group or fluoroalkyl group, or an aryl group which may have a substituent. １０ If there are two or more, then there are two or more R １０ They may be the same or different from each other. Ar is an aryl group which may have substituents. X ２ These are alkali metal ions or ammonium ions, X ３ It is a halide ion, X ４ It is a halogen atom, R is an alkyl group, L is a hydrolyzable group or a hydroxyl group, and the two or more Ls in T may be the same or different. a1 is an integer greater than or equal to 1, b1 is an integer greater than or equal to 2, c is 2 or 3, Two or more Ts may be the same or different. 【Chemistry 10】 (-A-Q １２ -) ｅ１ C(R ２ ) ４－ｅ１－ｅ２ (-Q ２２ -) ｅ２ (g2-2) -A-Q １３ -N(-Q ２３ -) ２ (g2-3) (-A-Q １４ -) ｈ１ Z(-Q ２４ -) ｈ２ (g2-4) (-A-Q １５ -) ｉ１ Si(R ３ ) ４－ｉ１－ｉ２ (-Q ２５ -) ｉ２ (g2-5) -A-Q １２ -CH(-Q ２２ -)-Si(R ３ ) ３－ｉ３ (-Q ２５ -) ｉ３ (g2-7) however, In equations (g2-1) to (g2-7), side A is R ｆ Connect to Q ２２ Q ２３ Q ２４ , and Q25 is connected to T, A is a single bond, -C(O)NR ６ -, -C(O)-, -OC(O)O-, -NHC(O)O-, -NHC(O)NR ６ -, -O-, or -SO ２ NR ６ - and Q １１ This refers to a single bond, -O-, an alkylene group, or an alkylene group with two or more carbon atoms with -C(O)NR between carbon atoms. ６ -, -C(O)-, -NR ６ A group having - or -O-, Q １２ This refers to a single bond, an alkylene group, or an alkylene group having two or more carbon atoms with -C(O)NR between carbon atoms. ６ -, -C(O)-, -NR ６ A group having - or -O-, Q １ Q １２ If you have two or more Q １２ They may be the same or different. Q １３ This includes single bonds (where A is -C(O)-), alkylene groups, and -C(O)NR between carbon atoms of alkylene groups with 2 or more carbon atoms. ６ -, -C(O)-, -NR ６ A group having - or -O-, or a group having -C(O)- at the N-side terminal of an alkylene group, Q １４ Q １４ If the atom at Z to which it is bonded is a carbon atom, then Q １２ Q １４ If the atom at Z to which the bond is formed is a nitrogen atom, then Q １３ Q １ Q １４ If you have two or more Q １４ They may be the same or different. Q １５ This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between carbon atoms. ６ -, -C(O)-, -NR ６ A group having - or -O-, Q １ Q １５ If you have two or more Q １５ They may be the same or different. Q ２２ This refers to an alkylene group, an alkylene group with 2 or more carbon atoms, with -C(O)NR between the carbon atoms. ６ -, -C(O)-, -NR ６ A group having - or -O-, or -C(O)NR at the non-T-connected end of an alkylene group. ６ -, -C(O)-, -NR ６ A group having - or -O-, or an alkylene group having 2 or more carbon atoms with -C(O)NR between carbon atoms. ６ -, -C(O)-, -NR ６ - or -O- and -C(O)NR at the end not connected to T ６ -, -C(O)-, -NR ６ A group having - or -O-, Q １ Q ２２ If you have two or more Q ２２ They may be the same or different. Q ２３ This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between carbon atoms. ６ -, -C(O)-, -NR ６ A group having - or -O-, and two Q ２３ They may be the same or different. Q ２４ Q ２４ If the atom at Z to which it is bonded is a carbon atom, then Q ２２ Q ２４ If the atom at Z to which the bond is formed is a nitrogen atom, then Q ２３ Q １ Q ２４ If you have two or more Q ２４ They may be the same or different. Q ２５ This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NR between carbon atoms. ６ -, -C(O)-, -NR ６ A group having - or -O-, Q １ Q ２５ If you have two or more Q ２５ They may be the same or different. Z is Q １４ It has a carbon or nitrogen atom that is directly bonded to it and Q ２４ It is a group having an a1+b1 valent ring structure with a carbon or nitrogen atom to which it is directly bonded, R １ Q is a hydrogen atom or an alkyl group, １ R １ If there are two or more, then there are two or more R １ They may be the same or different. R ２ is a hydrogen atom, a hydroxyl group, an alkyl group, or an acyloxy group. R ３ It is an alkyl group, R ６ These are a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. d1 is an integer between 0 and 3, d2 is an integer between 0 and 3, and d1 + d2 is an integer between 1 and 3. d3 is an integer between 0 and 3, d4 is an integer between 0 and 3, and d3 + d4 is an integer between 1 and 3. d1 + d3 is Q １ In this case, it is an integer from 1 to 5. d2 + d4 is Q １ In this case, it is an integer between 2 and 5. e1 + e2 is either 3 or 4. e1 is Q １ In this case, it is an integer from 1 to 3, e2 is Q １ In this case, it is an integer between 2 and 3. h1 is Q １ In this case, it is an integer greater than or equal to 1, h2 is an integer greater than or equal to 2, i1 + i2 is either 3 or 4. i1 is Q １ In this case, it is an integer from 1 to 3, i2 is Q １ In this case, it is an integer between 2 and 3. i3 is either 2 or 3.

5. T is -Si(R) ３－ｃ (L) ｃ The fluorine-containing ether compound according to claim 3 or 4. however, R is an alkyl group, L is a hydrolyzable group or a hydroxyl group, and the two or more Ls in T may be the same or different. c is either 2 or 3.

6. The fluorine-containing ether compound according to any one of claims 1 to 5, wherein the fluorine-containing ring structure is a four-membered ring.

7. A fluorine-containing ether compound according to any one of claims 1 to 6, wherein the number average molecular weight is 2,500 or more.

8. A fluorine-containing ether composition characterized by comprising one or more fluorine-containing ether compounds described in any one of claims 1 to 7, and other fluorine-containing ether compounds.

9. A fluorine-containing ether compound according to any one of claims 1 to 7 or a fluorine-containing ether composition according to claim 8, A coating liquid characterized by containing a liquid medium.

10. An article characterized by having a surface layer formed from a fluorine-containing ether compound according to any one of claims 1 to 7 or a fluorine-containing ether composition according to claim 8 on the surface of a substrate.

11. The article according to claim 10, wherein the surface layer is provided on the surface of a component that constitutes the surface of a touch panel that is touched by a finger.

12. A method for manufacturing an article, characterized by treating the surface of a substrate by a dry coating method using a fluorine-containing ether compound according to any one of claims 1 to 7 or a fluorine-containing ether composition according to claim 8, thereby forming a surface layer on the surface of the substrate made of the fluorine-containing ether compound or the fluorine-containing ether composition.

13. A method for manufacturing an article, characterized by applying the coating liquid described in claim 9 to the surface of a substrate by a wet coating method and drying it to form a surface layer on the surface of the substrate that is made of the fluorine-containing ether compound or the fluorine-containing ether composition.

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