Fluorinated ether compound, fluorinated ether composition, coating liquid and article

Abstract

To provide a fluorinated ether compound, a fluorinated ether composition and a coating liquid that can form a surface layer excellent in water / oil repellency, abrasion resistance, fingerprint stain removability, lubricity and outer appearance, and an article having such a surface layer.SOLUTION: A fluorinated ether compound is represented by A1-O-(Rf1O)m1-Q1-[C(O)N(R1)]p1-R11-C[-R12-SiR13n1X13-n1]3, where A1 is a C1-20 perfluoroalkyl group; Rf1 is a fluoroalkylene group having no branched structure; m1 is an integer from 2 to 210; Q1 is a single bond or a fluoroalkylene group having no branched structure; R1 is a hydrogen atom, etc.; p1 is 0 or 1; R11 is a single bond, an alkylene group, etc.; R12 is an alkylene group, etc.; R13 is a monovalent hydrocarbon group, etc.; X1 is a hydrolyzable group; and n1 is an integer of from 0 to 2.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a fluorinated ether compound, a fluorinated ether composition, a coating liquid, and an article. [Background technology]

[0002] Fluorine-containing compounds are suitable for use in surface treatment agents because they exhibit high lubricity, water and oil repellency, etc. When the surface of a substrate is imparted with water and oil repellency by the surface treatment agent, dirt on the substrate surface becomes easier to wipe off, improving dirt removability. Among these fluorine-containing compounds, fluorine-containing ether compounds having a poly(oxyperfluoroalkylene) chain in which an ether bond (-O-) exists in the middle of the perfluoroalkyl chain are particularly excellent in removing dirt such as oils and grease.

[0003] The surface treatment agent containing the fluorinated ether compound is used in applications where it is required that the performance of water and oil repellency not decreasing even when rubbed repeatedly with fingers (abrasion resistance) and the performance of fingerprints adhering to the surface can be easily removed by wiping (fingerprint stain removability) are maintained for a long period of time, such as as a surface treatment agent for members constituting the surface that is touched by fingers in a touch panel.

[0004] In order to impart abrasion resistance to a surface layer formed on the surface of a substrate, for example, a hydrolyzable silyl group may be introduced at the end of a fluorine-containing ether compound to chemically bond the fluorine-containing ether compound to the substrate. As a fluorine-containing ether compound intended to form a surface layer with excellent abrasion resistance, a fluorine-containing ether compound has been proposed in which three hydrolyzable silyl groups are introduced at each of both ends of the fluorine-containing ether compound via a branched structure of pentaerythritol (Patent Document 1). [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2014-070163 Summary of the Invention [Problem to be solved by the invention]

[0006] According to the findings of the present inventors, the fluorine-containing ether compound described in Patent Document 1 has the following problems. The hydrolyzable silyl groups at both ends of the fluorine-containing ether compound react with the substrate or react with one another, immobilizing both ends of the fluorine-containing ether compound. This results in insufficient lubricity (smoothness when touched with a finger) and abrasion resistance of the surface layer. The poly(oxyperfluoroalkylene) chain has a branched structure, which results in insufficient fingerprint removal and lubrication of the surface layer. The high content of non-fluorinated terminal moieties (a branched structure with pentaerythritol and three hydrolyzable silyl groups) tends to lead to a poor appearance of the surface layer. This is thought to be because the hydrolyzable silyl groups tend to aggregate between molecules of the fluorine-containing ether compound, and the hydrolyzable silyl groups aggregate and react with each other in the coating liquid, or during drying after the coating liquid has been applied to the surface of the substrate, forming an uneven layer.

[0007] The present invention aims to provide a fluorinated ether compound, a fluorinated ether composition and a coating liquid which are capable of forming a surface layer which is excellent in water and oil repellency, abrasion resistance, fingerprint stain removability, lubricity and appearance, and an article having a surface layer which is excellent in water and oil repellency, abrasion resistance, fingerprint stain removability, lubricity and appearance. [Means for solving the problem]

[0008] The present invention provides a fluorinated ether compound, a fluorinated ether composition, a coating liquid and an article having the following structures [1] to

[14] . [1] A fluorine-containing ether compound represented by the following formula (1): A 1 -O-(R f1 O) m1 -Q 1 -[C(O)N(R 1 )]p1 -R 11 -C[-R 12 -SiR 13 n1 X 1 3-n1 ]3···(1) however, A 1 is a perfluoroalkyl group having 1 to 20 carbon atoms, R f1 is a fluoroalkylene group having no branched structure, m1 is an integer from 2 to 210, (R f1 O) m1 is two or more types of R f1 O, Q 1 is a fluoroalkylene group that does not have a single bond or a branched structure, R 1 is a hydrogen atom or an alkyl group, p1 is 0 or 1, R 11 is a single bond, an alkylene group, or the terminal of an alkylene group (where C[-R 12 -SiR 13 n1 X 1 3-n1 ]3.) or a group having an etheric oxygen atom between carbon atoms of an alkylene group having two or more carbon atoms, or a group having an etheric oxygen atom between carbon atoms of an alkylene group having two or more carbon atoms (provided that C[-R 12 -SiR 13 n1 X 1 3-n1 ]3.) and a group having an etheric oxygen atom between carbon atoms, R 12 is an alkylene group, a group having an ethereal oxygen atom at the terminal of the alkylene group (excluding the terminal bonded to Si), or a group having an ethereal oxygen atom between carbon atoms of an alkylene group having two or more carbon atoms, R 13 is a hydrogen atom or a monovalent hydrocarbon group, X1 is a hydrolyzable group, n1 is an integer from 0 to 2, Three [-R 12 -SiR 13 n1 X 1 3-n1 ] do not all have to be the same group.

[0009] [2] The fluorinated ether compound according to [1], wherein the fluorinated ether compound represented by the formula (1) is a fluorinated ether compound represented by the following formula (1-1): A 1 -O-(R f5 O) m5 (R F1 O) m10 (R f6 O) m6 -Q 1 -[C(O)N(R 1 )] p1 -R 11 -C[-R 12 -SiR 13 n1 X 1 3-n1 ]3···(1-1) however, A 1 , Q 1 , R 1 , p1, R 11 , R 12 , R 13 , X 1 and n1 are the same as in formula (1), R F1 is a perfluoroalkylene group having no branched structure, m10 is an integer of 2 or more, and (R F1 O) m10 is two or more types of R F1 O, R f5 is a fluoroalkylene group containing one or more hydrogen atoms and not having a branched structure, m5 is an integer of 0 to 4, and when m5 is an integer of 2 to 4, (R f5 O) m5 is two or more types of R f5 O, Rf6 is a fluoroalkylene group containing one or more hydrogen atoms and not having a branched structure, m6 is an integer of 0 to 4, and when m6 is an integer of 2 to 4, (R f6 O) m6 is two or more types of R f6 O, m10+m5+m6=m1.

[0010] [3] R F1 is a perfluoroalkylene group having 1 to 6 carbon atoms, and R f5 , R f6 are each independently a fluoroalkylene group having 2 to 6 carbon atoms. [4]R f5 , R f6 are each independently a fluoroalkylene group having one or two hydrogen atoms. [5] When p1 is 0, m6 is 1 or 2 and Q 1 is a single bond, and R 11 binds to (R f6 O) is (R f7 CHO), When p1 is 1, m6 is 0 and Q 1 is a fluoroalkylene group. [6] The fluorine-containing ether compound according to any one of [2] to [5], wherein m10 is 5 or more.

[0011] [7] Q 1 The fluorine-containing ether compound of any one of [1] to [6], wherein when is a fluoroalkylene group, the fluoroalkylene group is a perfluoroalkylene group having 1 to 6 carbon atoms. [8] When p1 is 0, R 11 is an alkylene group having 1 to 4 carbon atoms, and when p1 is 1, R 11 is a single bond or an alkylene group having 1 to 4 carbon atoms. [9] R 12is an alkylene group having 2 to 6 carbon atoms or an alkylene group having 3 to 8 carbon atoms and having an etheric oxygen atom between carbon atoms.

[10] The fluorinated ether compound according to any one of [1] to [9], having a number average molecular weight of 500 to 20,000.

[0012]

[11] A fluorinated ether composition comprising the fluorinated ether compound of any one of [1] to

[10] above and a fluorinated ether compound other than the fluorinated ether compound represented by formula (1), the total proportion of the fluorinated ether compound represented by formula (1) and other fluorinated ether compounds in the fluorinated ether composition is 80 to 100% by mass relative to the fluorinated ether composition, A fluorinated ether composition characterized in that the ratio of the other fluorinated ether compound to the total of the fluorinated ether compound represented by formula (1) and the other fluorinated ether compound is more than 0 mass% and less than 40 mass%.

[12] The fluorinated ether composition according to

[11] , wherein the other fluorinated ether compound is at least one selected from the group consisting of the following fluorinated ether compound (2), the following fluorinated ether compound (3) and the following fluorinated ether compound (4): Fluorine-containing ether compound (2): In the fluorine-containing ether compound represented by the formula (1), the —C[—R 12 -SiR 13 n1 X 1 3-n1 ]3 is the group having the (R f1 O) m1 A fluorine-containing ether compound bonded to both sides of the Fluorine-containing ether compound (3): In the fluorine-containing ether compound represented by the formula (1), 1 The group having the formula (R f1 O) m1 A fluorine-containing ether compound bonded to both sides of the Fluorine-containing ether compound (4): In the fluorine-containing ether compound represented by the formula (1), the —C[—R12 -SiR 13 n1 X 1 3-n1 ]3 is -C[-R 12 -SiR 13 n1 X 1 3-n1 ] 3―t [-R 15 ] t (However, R 15 is HSiR 13 n1 X 1 3-n1 Adding -R 12 -SiR 13 n1 X 1 3-n1 or an isomer group of the unsaturated bond-containing group, and t is an integer of 1 to 3), a fluorine-containing ether compound.

[0013]

[13] A coating liquid comprising the fluorinated ether compound of any one of [1] to

[10] above or the fluorinated ether composition of

[11] or

[12] above, and a liquid medium.

[14] An article having a surface layer formed from the fluorinated ether compound of any one of [1] to

[10] above, or the fluorinated ether composition of

[11] or

[12] above. [Effects of the Invention]

[0014] The fluorinated ether compound, fluorinated ether composition and coating liquid of the present invention can form a surface layer that is excellent in water and oil repellency, abrasion resistance, fingerprint stain removability, lubricity and appearance. The article of the present invention has a surface layer that is excellent in water and oil repellency, abrasion resistance, fingerprint stain removability, lubricity, and appearance. DETAILED DESCRIPTION OF THE INVENTION

[0015] In this specification, the compound represented by formula (1) will be referred to as compound (1). Compounds represented by other formulas will also be referred to in the same manner. As used herein, the following terms have the following meanings: The term "perfluoroalkyl group" refers to an alkyl group in which all of the hydrogen atoms have been substituted with fluorine atoms. The term "fluoroalkylene group" refers to an alkylene group in which one or more hydrogen atoms have been substituted with a fluorine atom. The term "perfluoroalkylene group" refers to an alkylene group in which all of the hydrogen atoms have been substituted with fluorine atoms. The chemical formula of an oxyperfluoroalkylene group is represented by writing the oxygen atom to the right of the perfluoroalkylene group. The term "etheric oxygen atom" refers to an oxygen atom that forms an ether bond (-O-) between carbon atoms. The term "hydrolyzable silyl group" refers to a group that can form a silanol group (Si-OH) by hydrolysis. For example, SiR 13 n1 X 1 3-n1 is. The term "surface layer" refers to a layer formed on the surface of a substrate. The "number average molecular weight" of the fluorinated ether compound is calculated by the following method using NMR analysis. 1 H-NMR and 19 The number of oxyperfluoroalkylene groups is calculated by F-NMR using the number of oxyperfluoroalkylene groups (average value) based on the number of terminal groups. 1 or SiR 13 n1 X 1 3-n1 is.

[0016] [Fluorine-containing ether compounds] The fluorine-containing ether compound of the present invention (hereinafter also referred to as the present compound) is compound (1). A 1 -O-(R f1 O) m1 -Q 1 -[C(O)N(R 1 )] p1 -R11 -C[-R 12 -SiR 13 n1 X 1 3-n1 ]3···(1) However, A 1 is a perfluoroalkyl group having 1 to 20 carbon atoms; R f1 is a fluoroalkylene group having no branched structure; m1 is an integer of 2 to 210; (R f1 O) m1 is two or more types of R f1 O; Q 1 is a fluoroalkylene group having no single bond or branched structure; R 1 is a hydrogen atom or an alkyl group; p1 is 0 or 1; R 11 is a single bond, an alkylene group, or the terminal of an alkylene group (where C[-R 12 -SiR 13 n1 X 1 3-n1 ]3.) or a group having an etheric oxygen atom between carbon atoms of an alkylene group having two or more carbon atoms, or a group having an etheric oxygen atom between carbon atoms of an alkylene group having two or more carbon atoms (provided that C[-R 12 -SiR 13 n1 X 1 3-n1 ]3.) and a group having an etheric oxygen atom between carbon atoms; R 12 is an alkylene group, a group having an etheric oxygen atom at the terminal of the alkylene group (excluding the terminal bonded to Si), or a group having an etheric oxygen atom between carbon atoms of an alkylene group having two or more carbon atoms; R 13 is a hydrogen atom or a monovalent hydrocarbon group; X 1 is a hydrolyzable group; n1 is an integer of 0 to 2; and three [-R 12 -SiR 13 n1 X 1 3-n1 ] do not all have to be the same group.

[0017] (A 1 basis) A 1 As the alkyl group, a perfluoroalkyl group having 1 to 10 carbon atoms is preferred, a perfluoroalkyl group having 1 to 6 carbon atoms is more preferred, and a perfluoroalkyl group having 1 to 3 carbon atoms is particularly preferred, in terms of further improving the lubricity and abrasion resistance of the surface layer.

[0018] A 1 has CF3- at its terminal, one terminal of compound (1) is CF3- and the other terminal is a hydrolyzable silyl group. Compound (1) having this structure can form a surface layer with low surface energy, and the surface layer has excellent lubricity and abrasion resistance. On the other hand, conventional fluorine-containing ether compounds having hydrolyzable silyl groups at both terminals have insufficient lubricity and abrasion resistance of the surface layer.

[0019] ((R f1 O) m1 ) R f1 may be a perfluoroalkylene group having no branched structure, or a fluoroalkylene group having no branched structure and containing one or more hydrogen atoms. R f1 As the alkylene group, a fluoroalkylene group having 1 to 6 carbon atoms and not having a branched structure is preferred, and a fluoroalkylene group having 1 to 4 carbon atoms and not having a branched structure is more preferred, in order to provide a surface layer with even better abrasion resistance and fingerprint stain removability, and a fluoroalkylene group having 1 to 2 carbon atoms and not having a branched structure is particularly preferred, in order to provide a surface layer with even better lubricity.

[0020] Compound (1) is (R f1 O) m1 Therefore, it is possible to form a surface layer that is excellent in water and oil repellency, abrasion resistance, and fingerprint stain removability. Also, R f1 is a fluoroalkylene group having no branched structure, (R f1 O) m1has a linear structure. Compound (1) having this structure provides a surface layer with excellent abrasion resistance and lubricity. On the other hand, conventional fluorine-containing ether compounds in which the poly(oxyperfluoroalkylene) chain has a branched structure provide a surface layer with insufficient abrasion resistance and lubricity.

[0021] m1 is an integer of 2 to 210, preferably an integer of 5 to 160, and particularly preferably an integer of 10 to 110. When m1 is at least the lower limit of the above range, the surface layer has excellent water and oil repellency. When m1 is at most the upper limit of the above range, the surface layer has excellent abrasion resistance. That is, when the number average molecular weight of compound (1) is too large, the number of hydrolyzable silyl groups present per unit molecular weight decreases, and abrasion resistance decreases.

[0022] (R f1 O) m1 In this case, two or more types of R f1 If O is present, then each R f1 The bonding order of O is not limited. For example, two types of R f1 When O is present, two types of R f1 The Os may be arranged randomly, alternately, or in blocks. Two or more types of R f1 O exists if R f1 is a perfluoroalkylene group, two or more R with different carbon numbers f1 O exists. R f1 is a fluoroalkylene group having a hydrogen atom, at least one of the number of carbon atoms, the number of hydrogen atoms, and the bonding position of the hydrogen atom is different, or two or more R f1 This means that O exists. Two or more types of R f1 Regarding the arrangement of O, for example, in the case of the fluorine-containing ether compound of the example, {(CF2O) x1 (CF2CF2O) x2 The structure represented by} indicates that x1 (CF2O) and x2 (CF2CF2O) are randomly arranged. x3The structure represented by the formula indicates that x3 (CF2CF2O) and x3 (CF2CF2CF2CF2O) are alternately arranged.

[0023] (Q 1 basis) Q 1 Q may be a single bond, a perfluoroalkylene group having no branched structure, or a fluoroalkylene group having no branched structure and containing one or more hydrogen atoms. 1 Compound (1) having no branched structure can form a surface layer that is excellent in abrasion resistance and lubricity. Q 1 is R f1 or a fluoroalkylene group derived from a compound having an amide group and a hydrolyzable silyl group (for example, compound (30) described below) used in producing compound (1). Q 1 When is not a single bond, it preferably has 1 to 10 carbon atoms.

[0024] ([C(O)N(R 1 )] p1 basis) The properties of the fluorine-containing ether compound are almost the same whether p1 is 0 or 1. When p is 1, it has an amide bond, but Q 1 [C(O)N(R 1 By bonding at least one fluorine atom to the carbon atom at the end of the bond with ), the polarity of the amide bond is reduced, and the water and oil repellency of the surface layer is less likely to decrease. Whether p1 is 0 or 1 can be selected from the viewpoint of ease of production. [C(O)N(R 1 )] p1 R in the group 1 is preferably a hydrogen atom in view of ease of production of compound (1). R 1 When the alkyl group is an alkyl group, the alkyl group is preferably an alkyl group having 1 to 4 carbon atoms.

[0025] (R 11 basis) R11 Examples of the alkylene group include a single bond, an alkylene group having 1 to 10 carbon atoms, and the terminal end of an alkylene group having 1 to 10 carbon atoms (provided that C[-R 12 -SiR 13 n1 X 1 3-n1 ]3) at the end of the bond, a group having an etheric oxygen atom between carbon atoms of an alkylene group having 2 to 10 carbon atoms, or a group having an etheric oxygen atom between carbon atoms of an alkylene group having 2 to 10 carbon atoms (provided that C[-R 12 -SiR 13 n1 X 1 3-n1 ]3.) and groups having an etheric oxygen atom between carbon atoms are preferred. If p1 is 0, R 11 From the viewpoint of ease of production of compound (1), a single bond or an alkylene group having 4 or less carbon atoms is preferred, and a single bond, a methylene group, or a dimethylene group is more preferred. Examples of groups having an etheric oxygen atom include -CH2CHO-, -CH2CHOCH2-, etc. If p1 is 1, R 11 From the viewpoint of ease of production of compound (1), a single bond and an alkylene group having 4 or less carbon atoms are preferred, and a single bond, a methylene group and a dimethylene group are more preferred.

[0026] (R 12 basis) R 12 is preferably an alkylene group having 1 to 10 carbon atoms, a group having an etheric oxygen atom at the terminal of the alkylene group having 1 to 10 carbon atoms (excluding the terminal bonded to Si), or a group having an etheric oxygen atom between carbon atoms of an alkylene group having 2 to 10 carbon atoms. From the viewpoint of ease of production of compound (1), a group selected from the group consisting of -CH2CH2-, -CH2CH2CH2-, -CHOCH2CH2CH2-, -CHOCH2CH2CH2CH2CH2- and -OCH2CH2CH2- (wherein the right side bonds to Si) is preferred. R 12In terms of excellent light resistance of the surface layer, it is particularly preferable that the surface layer does not have an etheric oxygen atom. In touch panels for outdoor use (digital signage such as vending machines and information boards), in-vehicle touch panels, etc., light resistance is required for the surface layer. The three R in compound (1) 12 may or may not all be the same group.

[0027] (SiR 13 n1 X 1 3-n1 basis) SiR 13 n1 X 1 3-n1 is a hydrolyzable silyl group. Compound (1) has three hydrolyzable silyl groups at its terminals. Compound (1) with this structure forms a strong chemical bond with the substrate, resulting in a surface layer with excellent abrasion resistance. Furthermore, compound (1) has a hydrolyzable silyl group at only one end, and since compound (1) with this structure is less likely to aggregate, the surface layer has an excellent appearance.

[0028] X 1 is a hydrolyzable group. A hydrolyzable group is a group that becomes a hydroxyl group by hydrolysis. That is, the Si-X at the end of compound (1) 1 becomes a silanol group (Si-OH) through a hydrolysis reaction. The silanol group further reacts with other molecules to form a Si-O-Si bond. The silanol group also undergoes a dehydration condensation reaction with the hydroxyl group on the surface of the substrate (substrate-OH) to form a chemical bond (substrate-O-Si).

[0029] X 1 Examples of the alkoxy group include an alkoxy group, a halogen atom, an acyl group, an isocyanate group (-NCO), etc. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms. X 1 From the viewpoint of ease of production of compound (1), X is preferably an alkoxy group having 1 to 4 carbon atoms or a halogen atom. As the halogen atom, a chlorine atom is particularly preferred.1 As the alkyl group, an alkoxy group having 1 to 4 carbon atoms is preferred because it produces less outgassing during application and provides excellent storage stability of compound (1). When long-term storage stability of compound (1) is required, an ethoxy group is particularly preferred, and when the reaction time after application is to be short, a methoxy group is particularly preferred.

[0030] R 13 is a hydrogen atom or a monovalent hydrocarbon group. Examples of the monovalent hydrocarbon group include an alkyl group, a cycloalkyl group, an alkenyl group, and an allyl group. R 13 R is preferably a monovalent hydrocarbon group, and particularly preferably a monovalent saturated hydrocarbon group. The number of carbon atoms in the monovalent saturated hydrocarbon group is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 or 2. 13 When the number of carbon atoms is within this range, compound (1) can be easily produced.

[0031] n1 is preferably 0 or 1, and particularly preferably 0. 1 The presence of a plurality of groups makes the adhesion to the substrate stronger.

[0032] SiR 13 n1 X 1 3-n1 Preferred examples of the cations include Si(OCH3)3, SiCH3(OCH3)2, Si(OCH2CH3)3, SiCl3, Si(OCOCH3)3, and Si(NCO)3. From the viewpoint of ease of handling in industrial production, Si(OCH3)3 is particularly preferred. Three SiR in compound (1) 13 n1 X 1 3-n1 may or may not all be the same group. From the viewpoint of ease of production of compound (1), it is preferable that all are the same group.

[0033] (Preferred form of compound (1)) As the compound (1), the compound (1-1) is preferred in that it provides a surface layer with even better abrasion resistance and fingerprint stain removability. A 1 -O-(R f5 O) m5 (R F1 O) m10 (R f6 O) m6 -Q 1 -[C(O)N(R 1 )] p1 -R 11 -C[-R 12 -SiR 13 n1 X 1 3-n1 ]3···(1-1) however, A 1 , Q 1 , R 1 , p1, R 11 , R 12 , R 13 , X 1 and n1 are the same as in formula (1), R F1 is a perfluoroalkylene group having no branched structure, m10 is an integer of 2 or more, and (R F1 O) m10 is two or more types of R F1 O, R f5 is a fluoroalkylene group containing one or more hydrogen atoms and not having a branched structure, m5 is an integer of 0 to 4, and when m5 is an integer of 2 to 4, (R f5 O) m5 is two or more types of R f5 O, R f6 is a fluoroalkylene group containing one or more hydrogen atoms and not having a branched structure, m6 is an integer of 0 to 4, and when m6 is an integer of 2 to 4, (R f6 O) m6 is two or more types of R f6 O, m10+m5+m6=m1.

[0034] ((Rf5 O) m5 ) R f5 is a fluoroalkylene group containing one or more hydrogen atoms and not having a branched structure, preferably a fluoroalkylene group having 2 to 6 carbon atoms, and particularly preferably a fluoroalkylene group having 2 carbon atoms. The number of hydrogen atoms is preferably 1 to 4, and particularly preferably 1 or 2. (R f5 O) are preferably (CHFCF2O) and (CH2CF2O). m5 is preferably an integer of 0 to 2, more preferably 0 or 2. When m is 2, (R f5 O)2 is preferably (CHFCF2O)-(CH2CF2O).

[0035] ((R F1 O) m10 ) R F1 As the alkylene group, a perfluoroalkylene group having 1 to 6 carbon atoms and not having a branched structure is preferred, and a perfluoroalkylene group having 1 to 4 carbon atoms and not having a branched structure is more preferred, in order to provide a surface layer with even better abrasion resistance and fingerprint stain removability, and a perfluoroalkylene group having 1 to 2 carbon atoms and not having a branched structure is particularly preferred, in order to provide a surface layer with even better lubricity.

[0036] The compound (1-1) is (R F1 O) m10 Therefore, a surface layer having even more excellent water and oil repellency, abrasion resistance, and fingerprint stain removability can be formed. Also, R F1 is a perfluoroalkylene group that does not have a branched structure, (R F1 O) m10 The compound (1-1) having this structure has a linear chain structure, and the surface layer has excellent abrasion resistance and lubricity.

[0037] (R F1 O) m10 In the formula, two or more R with different carbon numbers are F1 If O is present, then each R F1The bonding order of O is not limited. For example, when CF2O and CF2CF2O are present, CF2O and CF2CF2O may be arranged randomly, alternately, or in blocks.

[0038] (R F1 O) m10 As for the surface layer, (CF2O) is preferred because it has excellent abrasion resistance, fingerprint removal properties, and lubricity. m11 (CF2CF2O) m12 , (CF2CF2O) m13、 (CF2CF2CF2O) m14、 (CF2CF2O-CF2CF2CF2CF2O) m15 is preferred, (CF2O) m11 (CF2CF2O) m12 is particularly preferred. However, m11 is an integer of 1 or more, m12 is an integer of 1 or more, and the bonding order of m11 CF2O and m12 CF2CF2O is not limited. Preferably, {(CF2O) m11 (CF2CF2O) m12 m13 and m14 are integers of 2 to 200, and m15 is an integer of 1 to 100.

[0039] ((R f6 O) m6 ) R f6 is a fluoroalkylene group containing one or more hydrogen atoms and not having a branched structure, and is preferably a fluoroalkylene group having 2 to 6 carbon atoms. The number of hydrogen atoms is preferably 1 to 4, and particularly preferably 1 or 2. m6 is preferably 0 to 2. If p1 is 0, Q 1 is preferably a single bond. In this case, (i.e., (R f6 O) m6 and R 11 is directly bonded), (R f6 O) m6 R in 11 Combine with (R f6 O) is (R f7 R is preferably a group represented by the formula (CH2O). f7 is Rf6 R is a group having one less carbon atom than R and is a perfluoroalkylene group or a fluoroalkylene group having a hydrogen atom. f7 is preferably a perfluoroalkylene group. f7 CH2O), (CF2CH2O), (CF2CF2CH2O), (CF2CF2CF2CH2O), (CF2CF2CF2CF2CH2O), etc. are preferred. In this case, m6 is preferably 1. If p1 is 1, m6 is 0 to 2 and Q 1 is preferably a fluoroalkylene group. 1 is preferably a perfluoroalkylene group. 1 The number of carbon atoms is more preferably 1 to 6.

[0040] m10+m5+m6 is an integer of 2 to 200, preferably an integer of 5 to 150, and particularly preferably an integer of 10 to 110. When m10+m5+m6 is at least the lower limit of the above range, the surface layer has excellent water and oil repellency. When m10+m5+m6 is not more than the upper limit of the above range, the surface layer has excellent abrasion resistance. That is, when the number average molecular weight of compound (1-1) is too large, the number of hydrolyzable silyl groups present per unit molecular weight decreases, and abrasion resistance decreases. m10 is more preferably an integer of 5 or more, and particularly preferably 10 or more.

[0041] (Preferred form of compound (1-1)) Examples of compound (1-1) include compounds of the following formula: This compound is preferred because it is easy to produce industrially, easy to handle, and provides a surface layer with excellent water and oil repellency, abrasion resistance, fingerprint stain removability, lubricity, and appearance.

[0042] Q 1 is a single bond and p1=0. In addition, "PFPE-CH2O-" and other "PFPE-" in the formula below are A 1 -O-(R f5 O) m5 (RF1 O) m10 (R f6 O) m6 - represents. [ka]

[0043] Q 1 is a perfluoroalkylene group and p1=1. In addition, "PFPE-R" in the chemical formula F -" is A 1 -O-(R f5 O) m5 (R F1 O) m10 (R f6 O) m6 -Q 1 - represents. [ka]

[0044] (Method for producing compound (1)) When p1 is 0, examples of the method for producing compound (1) include the following methods (10) to (15). When p1 is 1, examples of the method for producing compound (1) include the following methods (20) to (25).

[0045] <Method (10)> The starting material is the commercially available compound (10). HO-CH2-(CF2O)(R F1 O) x -CF2-CH2-OH (10)

[0046] In the presence of a basic compound, compound (10) is reacted with A 1 -O-CF=CF2 is reacted to obtain a mixture of compound (11), compound (3A) and unreacted compound (10). A 1 -O-CHFCF2OCH2-(CF2O)(R F1 O) x-CF2-CH2-OH (11) A 1 -O-CHFCF2OCH2-(CF2O)(R F1 O) x -CF2-CH2OCF2CHF-OA 1 (3A)

[0047] Compound (11) is isolated from the mixture, and then esterified with CFCFCFOCF(CF)C(O)F to obtain compound (12). The esterification reaction may be a reaction of compound (11) with other acid fluorides, acid chlorides, acid bromides, acid anhydrides, etc. A 1 -O-CHFCF2OCH2-(CF2O)(R F1 O) x -CF2-CH2-OC(O)CF(CF3)OCF2CF2CF3...(12)

[0048] The hydrogen atoms of compound (12) are substituted with fluorine atoms using fluorine gas to obtain compound (13). The fluorination step can be carried out, for example, according to the method described in WO 2000 / 56694. A 1 -O-(CF2CF2O)(CF2CF2O)(R F1 O) x (CF2CF2O)-C(O)CF(CF3)OCF2CF2CF3...(13)

[0049] Compound (13) can be treated with alcohol (methanol, ethanol, 1-propanol, 2-propanol, etc.). 10 It is written as OH. 10 is an alkyl group.) to give compound (14). A 1 -O-(CF2CF2O)(CF2CF2O)(R F1 O) x -CF2-C(O)OR 10 ···(14)

[0050] Compound (14) is reduced with hydrogen using a reducing agent (sodium borohydride, lithium aluminum hydride, etc.) to obtain compound (15). A 1 -O-(CF2CF2O)(CF2CF2O)(R F1 O) x -CF2-CH2OH (15)

[0051] Compound (16) is obtained by reacting compound (15) with CF3SO2Cl in the presence of a basic compound. A 1 -O-(CF2CF2O)(CF2CF2O)(R F1 O) x -CF2-CH2OSO2CF3···(16)

[0052] Compound (17) is obtained by reacting compound (16) with HOCH2C(CH2OCH2CH=CH2)3 in the presence of a basic compound. A 1 -O-(CF2CF2O)(CF2CF2O)(R F1 O) x -CF2-CH2OCH2-C(CH2OCH2CH=CH2)3...(17)

[0053] Compound (17) and HSiR 13 n1 X 1 3-n1 and the like are subjected to a hydrosilylation reaction to obtain compound (1A). The hydrosilylation reaction is preferably carried out using a transition metal catalyst such as platinum or a radical generator such as an organic peroxide. A 1 -O-(CF2CF2O)(CF2CF2O)(R F1 O) x -CF2-CH2OCH2-C[CH2OCH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1A) When the above formula is expressed collectively for each oxyfluoroalkylene unit, compound (1A) is expressed as follows. A 1-O-(CF2CF2O)(CF2CF2O)(R F1 O) x (CF2CH2O)-CH2C[CH2OCH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1A)

[0054] <Method (11)> The compound (11) obtained in the method (10) is used as the starting material. A 1 -O-CHFCF2OCH2-(CF2O)(R F1 O) x -CF2-CH2-OH (11)

[0055] Compound (16B) is obtained by reacting compound (11) with CF3SO2Cl in the presence of a basic compound. A 1 -O-CHFCF2OCH2-(CF2O)(R F1 O) x -CF2-CH2OSO2CF3···(16B)

[0056] Compound (17B) is obtained by reacting compound (16B) with HOCH2C(CH2OCH2CH=CH2)3 in the presence of a basic compound. A 1 -O-CHFCF2OCH2-(CF2O)(R F1 O) x -CF2-CH2OCH2-C(CH2OCH2CH=CH2)3...(17B)

[0057] Compound (17B) and HSiR 13 n1 X 1 3-n1 is subjected to a hydrosilylation reaction to obtain compound (1B). A 1 -O-CHFCF2OCH2-(CF2O)(R F1 O) x -CF2-CH2OCH2-C[CH2OCH2CH2CH2-SiR 13 n1 X1 3-n1 ]3···(1B) When the above formula is expressed collectively for each oxyfluoroalkylene unit, compound (1B) is expressed as follows. A 1 -O-(CHFCF2O)(CH2CF2O)(R F1 O) x (CF2CH2O)-CH2-C[CH2OCH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1B)

[0058] <Method (12)> The starting material is compound (15C) obtained by the method described in WO 2013 / 121984. A 1 -O-(R F1 O) x -Q 12 -CH2OH (15C) However, Q 12 is a perfluoroalkylene group having no branched structure.

[0059] Compound (15C) is reacted with CF3SO2Cl in the presence of a basic compound to give compound (16C). A 1 -O-(R F1 O) x -Q 12 -CH2OSO2CF3···(16C)

[0060] Compound (17C) is obtained by reacting compound (16C) with HOCH2C(CH2OCH2CH=CH2)3 in the presence of a basic compound. A 1 -O-(R F1 O) x -Q 12 -CH2OCH2-C(CH2OCH2CH=CH2)3...(17C)

[0061] Compound (17C) and HSiR 13 n1 X 13-n1 is subjected to a hydrosilylation reaction to obtain compound (1C). A 1 -O-(R F1 O) x -Q 12 -CH2OCH2-C[CH2OCH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1C) When the above formula is expressed collectively for each oxyfluoroalkylene unit, compound (1C) is expressed as follows. A 1 -O-(R F1 O) x (Q 12 CH2O)-CH2-C[CH2OCH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1C)

[0062] <Method (13)> Compound (20) is obtained by reacting HOCH2C(CH2CH=CH2)3 with (CF3SO2)2O. CF3SO2OCH2C(CH2CH=CH2)3...(20)

[0063] The compound (15) obtained in method (10) is used as the starting material. A 1 -O-(CF2CF2O)(CF2CF2O)(R F1 O) x -CF2-CH2OH (15) Here, x is an integer from 1 to 198.

[0064] Compound (17D) is obtained by reacting compound (15) with compound (20) in the presence of a basic compound. A 1 -O-(CF2CF2O)(CF2CF2O)(R F1 O) x -CF2-CH2OCH2-C(CH2CH=CH2)3...(17D)

[0065] Compound (17D) and HSiR 13 n1 X 1 3-n1 is subjected to a hydrosilylation reaction to obtain compound (1D). A 1 -O-(CF2CF2O)(CF2CF2O)(R F1 O) x -CF2-CH2OCH2-C[CH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1D) When the above formula is expressed collectively for each oxyfluoroalkylene unit, the compound (1D) is expressed as follows. A 1 -O-(CF2CF2O)(CF2CF2O)(R F1 O) x (CF2CH2O)-CH2-C[CH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1D)

[0066] <Method (14)> The compound (11) obtained in the method (10) is used as the starting material. A 1 -O-CHFCF2OCH2-(CF2O)(R F1 O) x -CF2-CH2-OH (11)

[0067] Compound (17E) is obtained by reacting compound (11) with compound (20) obtained in method (13) in the presence of a basic compound. A 1 -O-CHFCF2OCH2-(CF2O)(R F1 O) x -CF2-CH2OCH2-C(CH2CH=CH2)3...(17E)

[0068] Compound (17E) and HSiR 13 n1 X 13-n1 and the resulting compound (1E) is subjected to a hydrosilylation reaction. A 1 -O-CHFCF2OCH2-(CF2O)(R F1 O) x -CF2-CH2OCH2-C[CH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1E) When the above formula is expressed collectively for each oxyfluoroalkylene unit, the compound (1E) is expressed as follows. A 1 -O-(CHFCF2O)(CH2CF2O)(R F1 O) x (CF2CH2O)-CH2-C[CH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1E)

[0069] <Method (15)> The starting material is compound (15C) obtained by the method described in WO 2013 / 121984. A 1 -O-(R F1 O) x -Q 12 -CH2OH (15C) However, Q 12 is a perfluoroalkylene group having no branched structure.

[0070] Compound (17F) is obtained by reacting compound (15C) with compound (20) obtained in method (13) in the presence of a basic compound. A 1 -O-(R F1 O) x -Q 12 -CH2OCH2-C(CH2CH=CH2)3...(17F)

[0071] Compound (17F) and HSiR 13 n1 X 1 3-n1is subjected to a hydrosilylation reaction to obtain compound (1F). A 1 -O-(R F1 O) x -Q 12 -CH2OCH2-C[CH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1F) When the above formula is expressed collectively for each oxyfluoroalkylene unit, compound (1F) is expressed as follows. A 1 -O-(R F1 O) x (Q 12 CH2O)-CH2-C[CH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1F)

[0072] <Method (20)> The compound (14) obtained in method (10) is used as the starting material. A 1 -O-(CF2CF2O)(CF2CF2O)(R F1 O) x -CF2-C(O)OR 10 ···(14)

[0073] Compound (14) contains H2N-R 11 -C(CH2CH=CH2)3 is reacted to give compound (17G). A 1 -O-(CF2CF2O)(CF2CF2O)(R F1 O) x -CF2-C(O)NH-R 11 -C(CH2CH=CH2)3···(17G)

[0074] Compound (17G) and HSiR 13 n1 X 1 3-n1 is subjected to a hydrosilylation reaction to obtain compound (1G). A 1-O-(CF2CF2O)(CF2CF2O)(R F1 O) x -CF2-C(O)NH-R 11 -C[CH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1G)

[0075] <Method (21)> The compound (11) obtained in the method (10) is used as the starting material. A 1 -O-CHFCF2OCH2-(CF2O)(R F1 O) x -CF2-CH2-OH (11)

[0076] Compound (11) is oxidized to obtain compound (13H) according to the method described in J. Org. Chem., Vol. 64, 1999, pp. 2564-2566. A 1 -O-CHFCF2OCH2-(CF2O)(R F1 O) x -CF2-C(O)OH (13H)

[0077] Compound (13H) with R 10 By reacting with OH, compound (14H) is obtained. 1 -O-CHFCF2OCH2-(CF2O)(R F1 O) x -CF2-C(O)OR 10 ···(14H)

[0078] Compound (14H) H2N-R 11 -C(CH2CH=CH2)3 is reacted to give compound (17H). A 1 -O-CHFCF2OCH2-(CF2O)(R F1 O) x -CF2-C(O)NH-R 11 -C(CH2CH=CH2)3 (17H)

[0079] Compound (17H) and HSiR 13 n1 X 1 3-n1 is subjected to a hydrosilylation reaction to obtain compound (1H). A 1 -O-CHFCF2OCH2-(CF2O)(R F1 O) x -CF2-C(O)NH-R 11 -C[CH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1H) When the above formula is expressed collectively for each oxyfluoroalkylene unit, the compound (1H) is expressed as follows. A 1 -O-(CHFCF2O)(CH2CF2O)(R F1 O) x -CF2-C(O)NH-R 11 -C[CH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1H)

[0080] <Method (22)> The starting material used is compound (14I) obtained by the method described in WO 2013 / 121984. A 1 -O-(R F1 O) x -Q 12 -C(O)OR 10 ···(14I) However, Q 12 is a perfluoroalkylene group having no branched structure.

[0081] Compound (14I) with H2N-R 11 -C(CH2CH=CH2)3 to give compound (17I). A 1 -O-(R F1 O) x -Q 12 -C(O)NH-R 11 -C(CH2CH=CH2)3···(17I)

[0082] Compound (17I) and HSiR 13 n1 X 1 3-n1 is subjected to a hydrosilylation reaction to obtain compound (1I). A 1 -O-(R F1 O) x -Q 12 -C(O)NH-R 11 -C[CH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1I)

[0083] <Method (23)> CF2=CFOCF2CF2CF2-C(O)OCH3 and H2N-R 11 -C(CH2CH=CH2)3 to give compound (30). CF2=CFOCF2CF2CF2-C(O)NH-R 11 -C(CH2CH=CH2)3 (30)

[0084] The compound (15) obtained in method (10) is used as the starting material. A 1 -O-(CF2CF2O)(CF2CF2O)(R F1 O) x -CF2-CH2OH (15) Here, x is an integer from 1 to 198.

[0085] Compound (17J) is obtained by reacting compound (15) with compound (30) in the presence of a basic compound. A 1 -O-(CF2CF2O)(CF2CF2O)(R F1 O) x -CF2CH2OCF2CHFOCF2CF2CF2-C(O)NH-R 11 -C(CH2CH=CH2)3···(17J)

[0086] Compound (17J) and HSiR13 n1 X 1 3-n1 is subjected to a hydrosilylation reaction to obtain compound (1J). A 1 -O-(CF2CF2O)(CF2CF2O)(R F1 O) x -CF2CH2OCF2CHFOCF2CF2CF2-C(O)NH-R 11 -C[CH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1J) When the above formula is expressed collectively for each oxyfluoroalkylene unit, the compound (1J) is expressed as follows. A 1 -O-(CF2CF2O)(CF2CF2O)(R F1 O) x (CF2CH2O)(CF2CHFO)-CF2CF2CF2-C(O)NH-R 11 -C[CH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1J)

[0087] <Method (24)> The compound (11) obtained in the method (10) is used as the starting material. A 1 -O-CHFCF2OCH2-(CF2O)(R F1 O) x -CF2-CH2OH (11)

[0088] Compound (17K) is obtained by reacting compound (11) with compound (30) obtained in method (23) in the presence of a basic compound. A 1 -O-CHFCF2OCH2-(CF2O)(R F1 O) x -CF2CH2OCF2CHFOCF2CF2CF2-C(O)NH-R 11 -C(CH2CH=CH2)3···(17K)

[0089] Compound (17K) and HSiR 13 n1 X 1 3-n1 is subjected to a hydrosilylation reaction to obtain compound (1K). A 1 -O-CHFCF2OCH2-(CF2O)(R F1 O) x -CF2CH2OCF2CHFOCF2CF2CF2-C(O)NH-R 11 -C[CH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1K) When the above formula is expressed collectively for each oxyfluoroalkylene unit, the compound (1K) is expressed as follows. A 1 -O-(CHFCF2O)(CH2CF2O)(R F1 O) x (CF2CH2O)(CF2CHFO)-CF2CF2CF2-C(O)NH-R 11 -C[CH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1K)

[0090] <Method (25)> The starting material is compound (15C) obtained by the method described in WO 2013 / 121984. A 1 -O-(R F1 O) x -R F CH2OH (15C) where x is an integer from 1 to 200, and R F is a perfluoroalkylene group having no branched structure.

[0091] Compound (17L) is obtained by reacting compound (15C) with compound (30) obtained in method (23) in the presence of a basic compound. A 1 -O-(R F1 O) x -RF CH2OCF2CHFOCF2CF2CF2-C(O)NH-R 11 -C(CH2CH=CH2)3···(17L)

[0092] Compound (17L) and HSiR 13 n1 X 1 3-n1 and the compound (1L) is obtained by hydrosilylation reaction. A 1 -O-(R F1 O) x -R F CH2OCF2CHFOCF2CF2CF2-C(O)NH-R 11 -C[CH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1L) When the above formula is expressed collectively for each oxyfluoroalkylene unit, the compound (1L) is expressed as follows. A 1 -O-(R F1 O) x (R F CH2O)(CF2CHFO)-CF2CF2CF2-C(O)NH-R 11 -C[CH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3···(1L)

[0093] (This compound) The compound may be a single compound consisting of one type of compound (1), 1 , (R f1 O) m1 , Q 1 , R 1 , p1, R 11 , R 12 , SiR 13 n1 X 1 3-n1 It may also be a mixture of two or more types of compound (1) having different structures. In the present invention, the compound (1) which is a single compound means a group of compounds which are identical except that there is a distribution in the number of m1. For example, in the case of compound (1-1), (R F1 O) m10 is {(CF2O) m11 (CF2CF2O) m12 In the case of {(CF2O)}, the same compound group except for the distribution in m11 and m12 is m11 / m10 (CF2CF2O) m12 / m10} m10 The commercially available compound (10) is usually a compound that can be regarded as a single compound in the above sense, and therefore its (R F1 O) x The derivatives that do not change the part are the other parts (A 1 , Q 11 , Q 12 , R 1 , p1, R 11 , R 12 , SiR 13 n1 X 1 3-n1 etc.) are identical, they can be considered a single compound.

[0094] The number average molecular weight of the present compound is preferably from 500 to 20,000, more preferably from 800 to 10,000, and particularly preferably from 1,000 to 8,000. When the number average molecular weight is within this range, excellent abrasion resistance is achieved.

[0095] [Fluorine-containing ether composition] The fluorinated ether composition of the present invention (hereinafter also referred to as the present composition) is a composition containing compound (1) and a fluorinated ether compound other than compound (1). Examples of fluorinated ether compounds other than compound (1) (hereinafter also referred to as the other fluorinated ether compounds) include fluorinated ether compounds produced as by-products in the production process of compound (1), and known (particularly commercially available) fluorinated ether compounds used for the same applications as compound (1). It is preferred that the other fluorinated ether compounds are compounds that are unlikely to deteriorate the properties of compound (1), and that their content relative to compound (1) in the present composition is an amount that is unlikely to deteriorate the properties of compound (1). When the other fluorinated ether compound is a by-product in the production process of compound (1), the purification of compound (1) in the production of compound (1) becomes easy and the purification step can be simplified. When the other fluorinated ether compound is a known fluorinated ether compound used for the same purpose as compound (1), new effects such as complementing the properties of compound (1) may be exhibited.

[0096] The other fluorine-containing ether compound is preferably at least one selected from the group consisting of the following fluorine-containing ether compound (2), the following fluorine-containing ether compound (3) and the following fluorine-containing ether compound (4). Fluorine-containing ether compound (2): In the fluorine-containing ether compound represented by the formula (1), the —C[—R 12 -SiR 13 n1 X 1 3-n1 ]3 is the group having the (R f1 O) m1 A fluorine-containing ether compound bonded to both sides of the Fluorine-containing ether compound (3): In the fluorine-containing ether compound represented by the formula (1), 1 The group having the formula (R f1 O) m1 A fluorine-containing ether compound bonded to both sides of the Fluorine-containing ether compound (4): In the fluorine-containing ether compound represented by the formula (1), the —C[—R 12 -SiR 13 n1 X 1 3-n1 ]3 is -C[-R 12 -SiR 13 n1 X 1 3-n1 ] 3―t [-R 15 ] t (However, R 15 is HSiR 13 n1 X 1 3-n1 Adding -R 12 -SiR 13 n1 X 1 3-n1 or an isomer group of the unsaturated bond-containing group, and t is an integer of 1 to 3), a fluorine-containing ether compound. Since there is little risk of deteriorating the properties of compound (1), the fluorinated ether compound (2) is preferably compound (2) described below, the fluorinated ether compound (3) is preferably compound (3) described below, and the fluorinated ether compound (4) is preferably compound (4) described below.

[0097] (Compound (2)) The compound (2) is a fluorine-containing ether compound represented by the following formula (2). [X 2 3-n2 R 23 n2 Si-R 22 -]3C-R 21 -[N(R 2 )C(O)] p2 -(R f2 O) m2 -Q 2 -[C(O)N(R 2 )] p2 -R 21 -C[-R 22 -SiR 23 n2 X 2 3-n2]3···(2) However, R f2 is a fluoroalkylene group having no branched structure; m2 is an integer of 2 to 210; (R f2 O) m2 is two or more R with different carbon numbers. f2 O; Q 2 is a fluoroalkylene group having no branched structure; R 2 is a hydrogen atom or an alkyl group; p2 is 0 or 1, and the two p2s do not have to be the same number; R 21 is a single bond, an alkylene group, or the terminal of an alkylene group (where [X 2 3-n2 R 23 n2 Si-R 22 -]3C.) or an alkylene group having two or more carbon atoms and an ether oxygen atom between carbon atoms, or an alkylene group having two or more carbon atoms and an ether oxygen atom between carbon atoms (provided that [X 2 3-n2 R 23 n2 Si-R 22 -]3C and the end of the bond. ) and a group having an ether oxygen atom between carbon atoms, and two R 21 may not be the same group; R 22 is an alkylene group, a group having an etheric oxygen atom at the terminal of the alkylene group (excluding the terminal bonded to Si), or a group having an etheric oxygen atom between carbon atoms of an alkylene group having two or more carbon atoms; R 23 is a hydrogen atom or a monovalent hydrocarbon group; X 2 is a hydrolyzable group; n2 is an integer of 0 to 2; six [-R 22 -SiR 23 n2 X 2 3-n2 ] do not all have to be the same group.

[0098] (R f2 O) m2 , Q 2 , R 2 , p2, R21 , R 22 , SiR 23 n2 X 2 3-n2 are (R f1 O) m1 , Q 1 , R 1 , p1, R 11 , R 12 , SiR 13 n1 X 1 3-n1 The same can be mentioned as above, and the preferred embodiments are also the same. If p2 is 0, and R f2 is a fluoroalkylene group having no branched structure and containing two or more hydrogen atoms, and R 21 R f2 If there is no ether oxygen atom at the end of the bond with R f2 R 21 At least one fluorine atom is bonded to the terminal carbon atom on the side bonding to the If p2 is 0, and Q 2 is a fluoroalkylene group having no branched structure and containing two or more hydrogen atoms, and R 21 Q 2 If there is no etheric oxygen atom at the end of the bond with Q 2 R 21 At least one fluorine atom is bonded to the terminal carbon atom on the side bonding to the

[0099] (Preferred form of compound (2)) As the compound (2), the compound (2-1) is preferred in that it provides a surface layer with even better abrasion resistance and fingerprint stain removability. [X 2 3-n2 R 23 n2 Si-R 22 -]3C-R 21 -[N(R 2 )C(O)] p2 -Q 21 -(R F2 O) m20 -Q 22-[C(O)N(R 2 )] p2 -R 21 -C[-R 22 -SiR 23 n2 X 2 3-n2 ]3···(2-1) However, R 2 , p2, R 21 , R 22 , R 23 , X 2 and n2 are the same as in formula (2); Q 21 is a single bond, a fluoroalkylene group containing one or more hydrogen atoms and not having a branched structure, a group having an ethereal oxygen atom at the terminal of a fluoroalkylene group containing one or more hydrogen atoms and not having a branched structure (excluding the terminal on the side bonding to C(O)), a group having an ethereal oxygen atom between a carbon-carbon atom of a fluoroalkylene group containing one or more hydrogen atoms and not having a branched structure and having two or more carbon atoms, or a group having an ethereal oxygen atom between the terminal (excluding the terminal on the side bonding to C(O)) and a carbon-carbon atom of a fluoroalkylene group containing one or more hydrogen atoms and not having a branched structure and having two or more carbon atoms (provided that the number of oxygen atoms is 10 or less); R F2 is a perfluoroalkylene group having no branched structure; m20 is an integer of 2 to 200; (R F2 O) m20 is two or more R with different carbon numbers. F2 O; Q 22 is a group having an etheric oxygen atom between carbon atoms of a perfluoroalkylene group having no branched structure, a fluoroalkylene group having no branched structure and containing one or more hydrogen atoms, or a fluoroalkylene group having two or more carbon atoms and having no branched structure and containing one or more hydrogen atoms.

[0100] Q 21 , (R F2 O) m20 , Q 22 As for Q in compound (1-1), 11 , (R F1 O) m10 , Q12 The same can be mentioned as above, and the preferred embodiments are also the same. Q 21 is a fluoroalkylene group having no branched structure and containing one or more hydrogen atoms, or a group having an etheric oxygen atom between carbon atoms in a fluoroalkylene group having two or more carbon atoms and having no branched structure and containing one or more hydrogen atoms, and Q 21 (R F2 O) m20 If there is no etheric oxygen atom at the end of the bond with Q 21 (R F2 O) m20 At least one hydrogen atom is bonded to the terminal carbon atom on the side that bonds to the

[0101] (Method for producing compound (2)) When p2 is 0, examples of the method for producing compound (2) include the following methods (30) and (31). When p2 is 1, examples of the method for producing compound (2) include the following methods (40) and (41).

[0102] <Method(30)> The starting material is the commercially available compound (10). HO-CH2-CF2O(R F2 O) x -CF2-CH2-OH (10) Here, x is an integer from 1 to 199.

[0103] Compound (10) is reacted with CF3SO2Cl in the presence of a basic compound to give compound (18). CF3SO2OCH2-(CF2O)(R F2 O) x -CF2-CH2OSO2CF3···(18)

[0104] Compound (19) is obtained by reacting compound (18) with HOCH2C(CH2OCH2CH=CH2)3 in the presence of a basic compound. (CH2=CHCH2OCH2)3C-CH2OCH2-(CF2O)(RF2 O) x -CF2-CH2OCH2-C(CH2OCH2CH=CH2)3...(19)

[0105] Compound (19) and HSiR 23 n2 X 2 3-n2 is subjected to a hydrosilylation reaction to obtain compound (2A). [X 2 3-n2 R 23 n2 Si-CH2CH2CH2OCH2]3C-CH2OCH2-(CF2O)(R F2 O) x -CF2-CH2OCH2-C[CH2OCH2CH2CH2-SiR 23 n2 X 2 3-n2 ]3···(2A)

[0106] <Method(31)> The starting material is the commercially available compound (10). HO-CH2-(CF2O)(R F2 O) x -CF2-CH2-OH (10) Here, x is an integer from 1 to 199.

[0107] Compound (10) is reacted with compound (20) obtained in method (13) in the presence of a basic compound to obtain compound (19B). (CH2=CHCH2)3C-CH2OCH2-(CF2O)(R F2 O) x -CF2-CH2OCH2-C(CH2CH=CH2)3...(19B)

[0108] Compound (19B) and HSiR 23 n2 X 2 3-n2 is subjected to a hydrosilylation reaction to obtain compound (2B). [X 2 3-n2 R 23n2 Si-CH2CH2CH2]3C-CH2OCH2-(CF2O)(R F2 O) x -CF2-CH2OCH2-C[CH2CH2CH2-SiR 23 n2 X 2 3-n2 ]3···(2B)

[0109] <Method(40)> The starting material is the commercially available compound (10). HO-CH2-CF2O(R F2 O) x -CF2-CH2-OH (10) Here, x is an integer from 1 to 199.

[0110] Compound (10) is oxidized to obtain compound (25) according to the method described in J. Org. Chem., Vol. 64, 1999, pp. 2564-2566. HOC(O)-(CF2O)(R F2 O) x -CF2-C(O)OH (25)

[0111] Compound (25) contains R 10 By reacting with OH, compound (26) is obtained. R 10 OC(O)-(CF2O)(R F2 O) x -CF2-C(O)OR 10 ···(26)

[0112] Compound (26) contains H2N-R 21 -C(CH2CH=CH2)3 is reacted to give compound (27). (CH2=CHCH2)3C-R 21 -NHC(O)-(CF2O)(R F2 O) x -CF2-C(O)NH-R 21 -C(CH2CH=CH2)3 (27)

[0113] Compound (27) and HSiR23 n2 X 2 3-n2 is subjected to a hydrosilylation reaction to obtain compound (2C). [X 2 3-n2 R 23 n2 Si-CH2CH2CH2]3C-R 21 -NHC(O)-(CF2O)(R F2 O) x -CF2-C(O)NH-R 21 -C[CH2CH2CH2-SiR 23 n2 X 2 3-n2 ]3···(2C)

[0114] <Method(41)> The starting material is the commercially available compound (10). HOCH2-(CF2O)(R F2 O) x -CF2CH2OH (10) Here, x is an integer from 1 to 199.

[0115] Compound (10) is reacted with compound (30) obtained in method (23) in the presence of a basic compound to give compound (27D). (CH2=CHCH2)3C-R 21 -NHC(O)-CF2CF2CF2OCHFCF2OCH2-(CF2O)(R F2 O) x -CF2CH2OCF2CHFOCF2CF2CF2-C(O)NH-R 21 -C(CH2CH=CH2)3 (27D)

[0116] Compound (27D) and HSiR 23 n2 X 2 3-n2 is subjected to a hydrosilylation reaction to obtain compound (2D). [X 2 3-n2 R 23 n2 Si-CH2CH2CH2]3C-R21 -NHC(O)-CF2CF2CF2OCHFCF2OCH2-(CF2O)(R F2 O) x -CF2CH2OCF2CHFOCF2CF2CF2-C(O)NH-R 21 -C[CH2CH2CH2-SiR 23 n2 X 2 3-n2 ]3···(2D)

[0117] (Compound (3)) The compound (3) is a fluorine-containing ether compound represented by the following formula (3). A 31 -O-(R f3 O) m3 -A 32 ···(3) However, A 31 and A 32 are each independently a perfluoroalkyl group having 1 to 20 carbon atoms; R f3 is a fluoroalkylene group having no branched structure; m3 is an integer of 2 to 210; (R f3 O) m3 is two or more R with different carbon numbers. f3 It may consist of O.

[0118] A 31 , (R f3 O) m3 , A 32 As for A in compound (1), 1 , (R f1 O) m1 , A 1 In order to effectively utilize the compounds by-produced during the production of compound (1), the A 1 , (R f1 O) m1 , A 1 It is preferably the same as

[0119] (Preferred form of compound (3)) As the compound (3), the compound (3-1) is preferred in that it provides a surface layer with even better abrasion resistance and fingerprint stain removability. A 31 -OQ 31 -(R F3 O) m30 -[Q 32 -O] p3 -A 32 (3-1) However, A 31 and A 32 are each independently a perfluoroalkyl group having 1 to 20 carbon atoms; Q 31 represents a single bond, a fluoroalkylene group having no branched structure and containing one or more hydrogen atoms, or the terminal end of a fluoroalkylene group having no branched structure and containing one or more hydrogen atoms (provided that A 31 -O) and has an etheric oxygen atom between carbon atoms, or a group having an etheric oxygen atom between carbon atoms of a fluoroalkylene group having two or more carbon atoms and not having a branched structure containing one or more hydrogen atoms (excluding the terminal on the side bonding to A 31 -O) and a group having an etheric oxygen atom between carbon atoms (however, the number of oxygen atoms is 10 or less); Q 32 is a fluoroalkylene group having no branched structure and containing one or more hydrogen atoms, or a group having an etheric oxygen atom between carbon atoms in a fluoroalkylene group having two or more carbon atoms and having no branched structure and containing one or more hydrogen atoms (provided that the number of oxygen atoms is 10 or less); R F3 is a perfluoroalkylene group having no branched structure; m30 is an integer of 2 to 200; (R F3 O) m30 is two or more R with different carbon numbers. F3 O; p3 may consist of Q 31 is 0 if it is a single bond, and Q 31 is 1 if it is not a single bond.

[0120] A 31 , Q 31 , (R F3O) m30 , Q 32 , A 32 As for A in compound (1-1), 1 , Q 11 , (R F1 O) m10 , Q 11 (excluding single bonds), A 1 In order to effectively utilize the compounds by-produced during the production of compound (1-1), the A 1 , Q 11 , (R F1 O) m10 , Q 11 (excluding single bonds), A 1 It is preferably the same as Q 31 is a fluoroalkylene group having no branched structure and containing one or more hydrogen atoms, or a group having an etheric oxygen atom between carbon atoms in a fluoroalkylene group having two or more carbon atoms and having no branched structure and containing one or more hydrogen atoms, and Q 31 (R F3 O) m30 If there is no etheric oxygen atom at the end of the bond with Q 31 (R F3 O) m30 At least one hydrogen atom is bonded to the terminal carbon atom on the side that bonds to the

[0121] (Production method of compound (3)) Examples of methods for producing compound (3) include the following methods (50) and (51).

[0122] <Method(50)> Compound (3A) is isolated from the mixture of compound (11), compound (3A) and unreacted compound (10) obtained in method (10). A 31 -O-CHFCF2OCH2-(CF2O)(R F3 O) x -CF2-CH2OCF2CHF-OA 32 (3A)

[0123] <Method(51)> Compound (3A) is fluorinated with fluorine gas to obtain compound (3B). A 31 -O-(CF2CF2O)(CF2CF2O)(R F3 O) x (CF2CF2O)(CF2CF2O)-A 32 (3B)

[0124] Q 31 A commercially available product may be used as compound (3) in which is a single bond and p3 is 0. Examples of commercially available products include FOMBLIN (registered trademark) M, FOMBLIN (registered trademark) Y, and FOMBLIN (registered trademark) Z (all manufactured by Solvay Solexis), Krytox (registered trademark) (manufactured by DuPont), and Demnum (registered trademark) (manufactured by Daikin Industries, Ltd.).

[0125] Compound (4) is a compound having -C[-R 12 -SiR 13 n1 X 1 3-n1 ]3 is -C[-R 12 -SiR 13 n1 X 1 3-n1 ] 3―t [-R 15 ] t is a compound substituted with -C[-R 12 -SiR 13 n1 X 1 3-n1 ] 3―t [-R 15 ] t The rest of the compound is the same as compound (1). 15 is converted to [-R 12 -SiR 13 n1 X 1 3-n1 or an isomeric group thereof, and t is an integer of 1 to 3. As described above, the alkenyl group moiety having an unsaturated group at the terminal is HSiR 13 n1 X 1 3-n1 By the hydrosilylation reaction of adding [-R 12 -SiR 13 n1 X 1 3-n1 For example, HSiR is produced by -C(CH2CH=CH2)3. 13 n1 X 1 3-n1 By adding -C[-CH2CH2CH2-SiR 13 n1 X 1 3-n1 ]3. In this case, (CH2CH=CH2) is R 15 In the hydrosilylation reaction, R 15 In some cases, a side reaction occurs in which the terminal unsaturated group is isomerized to a non-terminal position, producing an alkenyl group called an inner olefin. For example, -CH2CH=CH2 is isomerizes to -CH=CHCH3. The alkenyl group portion with an unsaturated group at a non-terminal position is called HSiR. 13 n1 X 1 3-n1 It remains without reacting with In the hydrosilylation reaction for producing compound (1), R 15 If R remains unreacted, 15 When isomerized, the terminal becomes -C[-R 12 -SiR 13 n1 X 1 3-n1 ] 3―t [-R 15 ] t A compound represented by the formula (4) is produced as a by-product.

[0126] (Composition of the present composition) The total proportion of the present compound and other fluorinated ether compounds in the present composition is preferably 80 to 100% by mass, particularly preferably 85 to 100% by mass. That is, the proportion of impurities is preferably 20% by mass or less, particularly preferably 15% by mass or less. When the proportion of the present compound and other fluorinated ether compounds is within the above range, the surface layer has excellent water and oil repellency, abrasion resistance, fingerprint stain removability, lubricity, and appearance.

[0127] The ratio of the other fluorinated ether compounds to the total of the present compound and the other fluorinated ether compounds is preferably more than 0% by mass and less than 40% by mass, more preferably more than 0% by mass and less than 30% by mass, and particularly preferably more than 0% by mass and less than 20% by mass. That is, the ratio of the present compound is preferably more than 60% by mass 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. When the ratio of the present compound and the other fluorinated ether compounds is within the above range, the surface layer has excellent water and oil repellency, abrasion resistance, fingerprint stain removability, lubricity, and appearance.

[0128] When the composition contains at least one of the compounds (2), (3) and (4) as the other fluorinated ether compounds, the composition will have the following composition. The total proportion of the present compound, compound (2), compound (3), and compound (4) in the present ether composition is preferably more than 60% by mass and not more than 100% by mass, more preferably from 70 to 100% by mass, and particularly preferably from 80 to 100% by mass. That is, the total proportion of fluorinated ether compounds other than the present compound, compound (2), compound (3), and compound (4), and impurities is preferably less than 40% by mass, more preferably not more than 30% by mass, and particularly preferably not more than 20% by mass. The proportion of compound (2) relative to the total of this compound, compound (2), compound (3) and compound (4) is preferably 0% by mass or more and less than 40% by mass, more preferably 0 to 30% by mass, and particularly preferably 0 to 20% by mass. The proportions of compound (3) and compound (4) are the same as the proportion of compound (2). However, the proportion of the total of compound (2), compound (3) and compound (4) relative to the total of this compound, compound (2), compound (3) and compound (4) is preferably more than 0 mass% and less than 40 mass%, particularly preferably more than 0 mass% and 30 mass% or less. When the composition contains at least one of compound (2), compound (3) and compound (4) as the other fluorinated ether compound, so long as the composition has a composition within the above range, the surface layer will have excellent water and oil repellency, abrasion resistance, fingerprint stain removability, lubricity and appearance.

[0129] The present composition may contain impurities other than the present compound and other fluorinated ether compounds. Impurities other than the present compound and other fluorinated ether compounds include compounds that are unavoidable in the production of the present compound and other fluorinated ether compounds. The present composition does not contain a liquid medium as described below.

[0130] [Coating liquid] The coating liquid of the present invention (hereinafter also referred to as the present coating liquid) contains the present compound or the present composition and a liquid medium. The present coating liquid may be in a liquid state, and may be a solution or a dispersion. The present coating liquid is only required to contain the present compound or the present composition, and may contain impurities such as by-products produced in the manufacturing process of the present compound. The concentration of the present compound or the present composition in the present coating liquid is preferably from 0.001 to 10% by mass, particularly preferably from 0.1 to 1% by mass.

[0131] The liquid medium is preferably an organic solvent. The organic solvent may be a fluorine-based organic solvent, a non-fluorine-based organic solvent, or a mixture of both.

[0132] Examples of the fluorine-based organic solvent include fluorinated alkanes, fluorinated aromatic compounds, fluoroalkyl ethers, fluorinated alkylamines, and fluoroalcohols. The fluorinated alkane is preferably a compound having 4 to 8 carbon atoms. Commercially available products include, for example, C6F 13H (Asahi Glass Co., Ltd., Asahiklin (registered trademark) AC-2000), C6F 13 Examples include C2H5 (Asahiklin (registered trademark) AC-6000, manufactured by Asahi Glass Co., Ltd.) and C2F5CHFCHFCF3 (Vertrel (registered trademark) XF, manufactured by Chemours). Examples of the fluorinated aromatic compounds include hexafluorobenzene, trifluoromethylbenzene, perfluorotoluene, and bis(trifluoromethyl)benzene. The fluoroalkyl ether is preferably a compound having 4 to 12 carbon atoms. Commercially available products include, for example, CF3CH2OCF2CF2H (manufactured by Asahi Glass Co., Ltd., Asahiklin (registered trademark) AE-3000), C4F9OCH3 (manufactured by 3M, Novec (registered trademark) 7100), C4F9OC2H5 (manufactured by 3M, Novec (registered trademark) 7200), and C2F5CF(OCH3)C3F7 (manufactured by 3M, Novec (registered trademark) 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-fluorinated organic solvents are compounds consisting only of hydrogen atoms and carbon atoms, and compounds consisting only of hydrogen atoms, carbon atoms, and oxygen atoms, and examples thereof include hydrocarbon organic solvents, alcohol organic solvents, ketone organic solvents, ether organic solvents, and ester organic solvents. The present coating liquid preferably contains 90 to 99.999 mass % of the liquid medium, and particularly preferably 99 to 99.9 mass %.

[0133] The present coating liquid may contain other components in addition to the present compound and liquid medium, as long as the effects of the present invention are not impaired. Examples of other components include known additives such as acid catalysts and base catalysts that promote the hydrolysis and condensation reaction of hydrolyzable silyl groups. The proportion of other components in the present coating liquid is preferably 10% by mass or less, particularly preferably 1% by mass or less.

[0134] The solids concentration of the coating liquid is preferably 0.001 to 10% by mass, and particularly preferably 0.01 to 1% by mass. The solids concentration of the coating liquid is a value calculated from the mass of the coating liquid before heating and the mass after heating for 4 hours in a convection dryer at 120°C. The concentration of the composition can be calculated from the solids concentration and the amounts of the composition, solvent, etc.

[0135] [Goods] The article of the present invention has a surface layer formed from the present compound or composition on the surface of a substrate.

[0136] (Surface layer) In the present compound or composition, the hydrolyzable silyl group (SiR 13 n1 X 1 3-n1 ) undergoes a hydrolysis reaction to form silanol groups (Si-OH), and the silanol groups react with each other to form Si-O-Si bonds, or the silanol groups undergo a dehydration condensation reaction with hydroxyl groups (substrate-OH) on the surface of the substrate to form chemical bonds (substrate-O-Si). That is, the surface layer in the present invention contains the present compound in a state in which some or all of the hydrolyzable silyl groups of the compound have undergone a hydrolysis reaction.

[0137] The thickness of the surface layer is preferably 1 to 100 nm, and particularly preferably 1 to 50 nm. When the thickness of the surface layer is equal to or greater than the lower limit of the above range, the effect of the surface treatment is easily obtained. When the thickness of the surface layer is equal to or less than the upper limit of the above range, the utilization efficiency is high. The thickness of the surface layer can be calculated from the oscillation period of an interference pattern of reflected X-rays obtained by X-ray reflectivity using a thin film analysis X-ray diffractometer (ATX-G, manufactured by RIGAKU Corporation).

[0138] (base material) The substrate in the present invention is not particularly limited as long as it is a substrate that is required to be imparted with water and oil repellency. Examples of the substrate material include metal, resin, glass, sapphire, ceramic, stone, and composite materials thereof. Glass may be chemically strengthened. The substrate may be surface-treated with SiO2 or the like. The substrate is preferably a substrate for a touch panel or a substrate for a display, and particularly preferably a substrate for a touch panel. The substrate for a touch panel has light-transmitting properties. "Having light-transmitting properties" means that the normal incidence visible light transmittance according to JIS R 3106:1998 (ISO 9050:1990) is 25% or more. The material for the substrate for a touch panel is preferably glass or a transparent resin.

[0139] (Article manufacturing method) The article of the present invention can be produced, for example, by the following method. A method for obtaining the article of the present invention, which comprises treating the surface of a substrate with the present compound or composition by a dry coating method. A method for obtaining the article of the present invention by applying the coating liquid to the surface of a substrate by a wet coating method and drying it.

[0140] <Dry coating method> The present compound and composition can be used directly in a dry coating method. The present compound and composition are suitable for forming a surface layer with excellent adhesion by a dry coating method. Dry coating methods include vacuum deposition, CVD, sputtering, and the like. The vacuum deposition method is suitable for use in terms of suppressing decomposition of the present compound and the simplicity of the equipment.

[0141] <Wet coating method> Wet coating methods include spin coating, wipe coating, spray coating, squeegee coating, dip coating, die coating, inkjet coating, flow coating, roll coating, casting, Langmuir-Blodgett coating, and gravure coating.

[0142] <Post-processing> In order to improve the abrasion resistance of the surface layer, an operation for promoting the reaction between the present compound and the substrate may be carried out as necessary. Such an operation includes heating, humidification, light irradiation, etc. For example, by heating the substrate on which the surface layer has been formed in a humid atmosphere, reactions such as the hydrolysis reaction of hydrolyzable silyl groups to silanol groups, the reaction of hydroxyl groups on the surface of the substrate with silanol groups, and the formation of siloxane bonds through the condensation reaction of silanol groups can be promoted. After the surface treatment, compounds in the surface layer that are not chemically bonded to other compounds or the substrate may be removed as needed, for example, by pouring a solvent over the surface layer or wiping it off with a cloth soaked in the solvent. [Example]

[0143] The present invention will be explained in more detail below using examples, but the present invention is not limited to these examples. Hereinafter, "%" means "% by mass" unless otherwise specified. A mixture consisting of two or more types of compound (1) will be referred to as a "compound," and a composition consisting of compound (1) and another fluorine-containing ether compound will be referred to as a "composition." Examples 1 to 6, 11 to 16, 17 to 22, 27 to 36, 38 to 41, 43 to 45 and 48 to 53 are working examples, and Examples 7 to 10, 23 to 26, 37, 42, 46 and 47 are comparative examples.

[0144] [Example 1: Production of Compound (1A-1) and Compound (3A-1)] (Example 1-1) A 300 mL three-neck flask was charged with 24.4 g of 24% KOH aqueous solution, 33 g of tert-butyl alcohol, and 220 g of compound (10-1) (manufactured by Solvay Solexis, FLUOROLINK (registered trademark) D4000), followed by the addition of 19.4 g of CFCFCF-O-CF=CF (manufactured by Tokyo Chemical Industry Co., Ltd.). The mixture was stirred at 60°C for 8 hours under a nitrogen atmosphere. After washing once with a dilute hydrochloric acid aqueous solution, the organic phase was recovered and concentrated using an evaporator to obtain 233 g of crude product (a). The crude product (a) was separated by silica gel column chromatography. CF was used as the developing solvent. 13 CH2CH3 (Asahi Glass Co., Ltd., AC-6000), AC-6000 / CF3CH2OCF2CF2H (Asahi Glass Co., Ltd., AE-3000) = 1 / 2 (mass ratio), and AE-3000 / ethyl acetate = 9 / 1 (mass ratio) were used in this order. For each fraction, the average values of the terminal group structure and the number of constituent units (x1, x2) were calculated. 1 H-NMR and 19 The F-NMR integral values were used to determine the content of compound (11-1), compound (3A-1), and compound (10-1), which were determined to be 42 mol%, 49 mol%, and 9 mol%, respectively, of crude product (a). 98.6 g (yield: 44.8%) of compound (11-1) and 51.9 g (yield: 23.6%) of compound (3A-1) were obtained. HO-CH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2-OH (10-1) CF3CF2CF2-O-CHFCF2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2-OH (11-1) CF3CF2CF2-O-CHFCF2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OCF2CHF-O-CF2CF2CF3...(3A-1)

[0145] NMR spectrum of compound (11-1); 1H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.9 (2H), 4.2 (2H), 5.8~6.0 (1H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.8 (42F), -78.8 (1F), -80.8 (1F), -81.4 (1F), -82.2 (3F), -83.5 (1F), -85.3 to -88.2 (2F), -89.4 to -91.1 (82F), -130.5 (2F), -145.1 (1F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (11-1): 4,150.

[0146] NMR spectrum of compound (3A-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 4.2 (4H), 5.8~6.0 (2H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.8 (42F), -78.8 (2F), -80.7 (2F), -82.2 (6F), -85.3 to -88.2 (4F), -89.4 to -91.1 (84F), -130.5 (4F), -145.1 (2F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (3A-1): 4,420.

[0147] (Example 1-2) In a 100 mL recovery flask, 30.0 g of compound (11-1), 0.9 g of sodium fluoride powder, and 30 g of dichloropentafluoropropane (AK-225, manufactured by Asahi Glass Co., Ltd.) were placed, and 3.5 g of CFCFCFOCF(CF)C(O)F was added. The mixture was stirred at 50°C for 24 hours under a nitrogen atmosphere. After removing the sodium fluoride powder using a pressure filter, excess CFCFCFOCF(CF)C(O)F and AK-225 were distilled off under reduced pressure. The resulting crude product was purified by CF 13The solution was diluted with HCl (AC-2000, manufactured by Asahi Glass Co., Ltd.), passed through a silica gel column, and the collected solution was concentrated with an evaporator to obtain 31.8 g (yield 98.8%) of compound (12-1). CF3CF2CF2-O-CHFCF2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2-OC(O)CF(CF3)OCF2CF2CF3...(12-1)

[0148] NMR spectrum of compound (12-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 4.2 (2H), 4.7 (2H), 5.8~6.0 (1H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.8 (42F), -78.8 to -88.2 (17F), -89.4 to -91.1 (82F), -130.3 (2F), -130.5 (2F), -132.5 (1F), -145.1 (1F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (12-1): 4,460.

[0149] (Example 1-3) A condenser maintained at 20°C, a packed bed of NaF pellets, and another condenser maintained at 0°C were installed in series at the gas outlet of a 1-liter nickel autoclave. A liquid return line was installed to return the condensed liquid from the condenser maintained at 0°C to the autoclave. An autoclave was charged with 750 g of ClCF2CFClCF2OCF2CF2Cl (hereinafter also referred to as CFE-419) and stirred while maintaining the temperature at 25°C. Nitrogen gas was bubbled into the autoclave at 25°C for 1 hour, and then 20% fluorine gas was bubbled in at 25°C at a flow rate of 2.0 L / h for 1 hour. While the 20% fluorine gas was bubbled in at the same flow rate, a solution of 31.0 g of compound (12-1) dissolved in 124 g of CFE-419 was injected into the autoclave over 4.3 hours. While the 20% fluorine gas was bubbled in at the same flow rate, the internal pressure of the autoclave was increased to 0.15 MPa (gauge pressure). 4 mL of a benzene solution containing 0.05 g / mL of benzene in CFE-419 was bubbled into the autoclave while heating from 25°C to 40°C, and the benzene solution inlet of the autoclave was closed. After stirring for 15 minutes, 4 mL of the benzene solution was again injected while maintaining the temperature at 40°C, and the injection port was closed. The same procedure was repeated three more times. The total amount of benzene injected was 0.17 g. Stirring was continued for 1 hour while blowing in 20% fluorine gas at the same flow rate. The pressure inside the autoclave was adjusted to atmospheric pressure, and nitrogen gas was blown in for 1 hour. The contents of the autoclave were concentrated using an evaporator to obtain 31.1 g of compound (13-1) (yield 98.5%). CF3CF2CF2-O-(CF2CF2O)(CF2CF2O){(CF2O) x1 (CF2CF2O) x2}(CF2CF2O)-C(O)CF(CF3)OCF2CF2CF3...(13-1)

[0150] NMR spectrum of compound (13-1); 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.7 (42F), -78.8 to -88.1 (11F), -89.4 to -91.1 (92F), -91.5 (2F), -130.3 (2F), -130.5 (2F), -132.5 (1F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (13-1): 4,550.

[0151] (Example 1-4) 30.0 g of compound (13-1) and 60 g of AK-225 were placed in a round-bottom flask made of tetrafluoroethylene-perfluoro(alkoxyvinyl ether) copolymer (hereinafter also referred to as PFA). The mixture was stirred while cooled in an ice bath, and 2.0 g of methanol was slowly added dropwise from the dropping funnel under a nitrogen atmosphere. The mixture was stirred for 12 hours while bubbling with nitrogen. The reaction mixture was concentrated using an evaporator to obtain 27.6 g of compound (14-1) (yield 98.8%). CF3CF2CF2-O-(CF2CF2O)(CF2CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-C(O)OCH3···(14-1)

[0152] NMR spectrum of compound (14-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.9 (3H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.8 (42F), -82.2 (3F), -89.4 to -91.1 (92F), -130.5 (2F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (14-1): 4,230.

[0153] (Example 1-5) In a 100 mL three-necked eggplant flask, 0.18 g of lithium chloride was dissolved in 18.3 g of ethanol. 25.0 g of compound (14-1) was added and cooled in an ice bath. A solution of 0.75 g of sodium borohydride in 22.5 g of ethanol was slowly added dropwise. The ice bath was removed, and the mixture was allowed to warm slowly to room temperature while stirring. After stirring at room temperature for 12 hours, aqueous hydrochloric acid was added dropwise until the mixture became acidic. 20 mL of AC-2000 was added, and the mixture was washed once with water and once with saturated saline, and the organic phase was recovered. The recovered organic phase was concentrated using an evaporator to obtain 24.6 g of compound (15-1) (yield 99.0%). CF3CF2CF2-O-(CF2CF2O)(CF2CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OH ···(15-1).

[0154] NMR spectrum of compound (15-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.9 (2H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.7 (42F), -81.4 (1F), -82.2 (3F), -83.4 (1F), -89.4 to -91.1 (90F), -130.5 (2F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (15-1): 4,200.

[0155] (Example 1-6) A 100 mL two-necked flask was charged with 20.0 g of compound (15-1), 20.0 g of 1,3-bis(trifluoromethyl)benzene (Tokyo Chemical Industry Co., Ltd.), 1.01 g of CFSOCl (Wako Pure Chemical Industries, Ltd.), and 1.00 g of triethylamine, and the mixture was stirred at room temperature for 4 hours under a nitrogen atmosphere. After the reaction was completed, 15 g of AK-225 was added, and the mixture was washed once with water and once with saturated saline, and the organic phase was recovered. The recovered organic phase was concentrated using an evaporator to obtain 20.3 g of compound (16-1) (yield 99%). CF3CF2CF2-O-(CF2CF2O)(CF2CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OSO2CF3···(16-1)

[0156] NMR spectrum of compound (16-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 4.6 (2H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.7 (42F), -74.1 (3F), -76.1 (1F), -79.5 (1F), -82.2 (3F), -89.4 to -91.1 (90F), -130.5 (2F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (16-1): 4,340.

[0157] (Example 1-7) In a 50 mL recovery flask, 0.13 g of sodium hydride (55% / paraffin) was suspended in 5.0 g of 1,3-bis(trifluoromethyl)benzene (Tokyo Chemical Industry Co., Ltd.), and 10.0 g of compound (16-1) was added dropwise at room temperature. 0.91 g of HOCH2C(CHOCH2CH=CH2)3 (purified product of Neoallyl (registered trademark) P-30M, Daiso Co., Ltd.) was added, the temperature was raised to 70 °C, and the mixture was stirred for 12 hours. After the reaction was completed, 15 g of AK-225 was added, washed with water, and the organic phase was recovered and concentrated using an evaporator. This was purified by silica gel column chromatography (developing solvent: AE-3000 / ethyl acetate = 99 / 1 (mass ratio)) to obtain 2.6 g of compound (17-1) (yield 26%). CF3CF2CF2-O-(CF2CF2O)(CF2CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OCH2-C(CH2OCH2CH=CH2)3...(17-1)

[0158] NMR spectrum of compound (17-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.6 (6H), 3.7~3.9 (10H), 5.1 (6H), 5.8 (3H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.7 (42F), -77.2 (1F), -79.4 (1F), -82.2 (3F), -89.4 to -91.1 (90F), -130.5 (2F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (17-1): 4,450.

[0159] (Example 1-8) A 10 mL PFA vessel was charged with 2.0 g of compound (17-1), 0.002 g of a xylene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 2%), 0.24 g of HSi(OCH3)3, 0.003 g of dimethyl sulfoxide, and 0.15 g of 1,3-bis(trifluoromethyl)benzene (Tokyo Chemical Industry Co., Ltd.), and the mixture was stirred at 40 °C for 4 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and the mixture was filtered through a 0.2 μm pore membrane filter to obtain 1.9 g (92% yield) of composition (1), consisting of compound (1A-1) in which the three allyl groups of compound (17-1) were hydrosilylated, and a by-product in which some or all of the three allyl groups of compound (17-1) were isomerized to the inner olefin (-CH=CHCH3). The conversion rate of the hydrosilylation was 100%, with no compound (17-1) remaining, and the selectivity of the hydrosilylation was 85%. CF3CF2CF2-O-(CF2CF2O)(CF2CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OCH2-C[CH2OCH2CH2CH2-Si(OCH3)3]3...(1A-1)

[0160] NMR spectrum of compound (1A-1); 1H-NMR (300.4 MHz, solvent: CDCl3, standard: TMS) δ (ppm): 0.7 (6H), 1.7 (6H), 3.4-3.8 (44H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.7 (42F), -77.2 (1F), -79.4 (1F), -82.2 (3F), -89.4 to -91.1 (90F), -130.5 (2F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (1A-1): 4,810.

[0161] [Example 2: Preparation of compound (1B-1)] (Example 2-1) The same procedure as in Example 1-6 was repeated, except that compound (15-1) was changed to 30.0 g of compound (11-1) obtained in Example 1-1, the amount of 1,3-bis(trifluoromethyl)benzene (manufactured by Tokyo Chemical Industry Co., Ltd.) was changed to 30.0 g, the amount of CFSOCl (manufactured by Wako Pure Chemical Industries, Ltd.) was changed to 1.44 g, and the amount of triethylamine was changed to 1.45 g, to give 30.6 g (yield 99%) of compound (16B-1). CF3CF2CF2-O-CHFCF2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OSO2CF3···(16B-1)

[0162] NMR spectrum of compound (16B-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 4.2 (2H), 4.6 (2H), 5.8~6.0 (1H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -51.2 to -54.6 (42F), -74.1 (3F), -77.6 (1F), -77.6 (2F), -79.0 (1F), -79.5 (1F), -81.2 (3F), -84.3 to -87.2 (2F), -87.9 to -91.0 (82F), -129.4 (2F), -144.1 (1F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (16B-1): 4,280.

[0163] (Example 2-2) Compound (17B-1) (2.4 g, yield 24%) was obtained in the same manner as in Example 1-7, except that compound (16-1) was changed to compound (16B-1) and the amount of HOCH2C(CH2OCH2CH=CH2)3 was changed to 0.92 g. CF3CF2CF2-O-CHFCF2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OCH2-C(CH2OCH2CH=CH2)3...(17B-1)

[0164] NMR spectrum of compound (17B-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.6 (6H), 3.7~3.9 (10H), 4.2 (2H), 5.1 (6H), 5.7~6.0 (4H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -51.2 to -54.6 (42F), -77.2 (1F), -77.7 (1F), -79.3 (1F), -79.7 (1F), -81.2 (3F), -84.3 to -87.2 (2F), -87.9 to -91.0 (82F), -129.4 (2F), -144.1 (1F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (17B-1): 4,390.

[0165] (Example 2-3) The procedure was the same as in Example 1-8, except that compound (17-1) was replaced with 1.8 g of compound (17B-1) obtained in Example 2-2 and the amount of HSi(OCH3)3 was changed to 0.22 g. This procedure yielded 1.7 g (87% yield) of composition (2), consisting of compound (1B-1) in which the three allyl groups of compound (17B-1) were hydrosilylated, and a by-product in which some or all of the three allyl groups of compound (17B-1) were isomerized to inner olefins (-CH=CHCH3). The hydrosilylation conversion was 100%, and no compound (17B-1) remained. The hydrosilylation selectivity was 87%. CF3CF2CF2-O-CHFCF2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OCH2-C[CH2OCH2CH2CH2-Si(OCH3)3]3...(1B-1)

[0166] NMR spectrum of compound (1B-1); 1 H-NMR (300.4 MHz, solvent: CDCl3, standard: TMS) δ (ppm): 0.7 (6H), 1.7 (6H), 3.4-3.8 (44H), 4.2 (2H), 5.8-6.0 (1H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -51.2 to -54.6 (42F), -77.2 (1F), -77.7 (1F), -79.3 (1F), -79.7 (1F), -81.2 (3F), -84.3 to -87.2 (2F), -87.9 to -91.0 (82F), -129.4 (2F), -144.1 (1F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (1B-1): 4,760.

[0167] [Example 3: Preparation of compound (1C-1)] (Example 3-1) Compound (15C-1) was obtained according to the method described in Example 7 of WO 2013 / 121984. CF3-O-(CF2CF2O-CF2CF2CF2CF2O) x3(CF2CF2O)-CF2CF2CF2-CH2OH ···(15C-1).

[0168] NMR spectrum of compound (15C-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 2.0 (1H), 4.0 (2H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -56.2 (3F), -84.1 (54F), -89.3 (54F), -91.4 (2F), -123.7 (2F), -126.6 (52F), -128.7 (2F). The average value of the number of units x3: 13, and the number average molecular weight of compound (15C-1): 4,700.

[0169] (Example 3-2) Compound (15-1) was obtained from compound (15C-1) obtained in Example 3-1, and 30.6 g (yield 99%) of compound (16C-1) was obtained in the same manner as in Example 1-6, except that the amount of CF3SO2Cl (manufactured by Wako Pure Chemical Industries, Ltd.) was changed to 0.86 g and the amount of triethylamine was changed to 1.02 g. CF3-O-(CF2CF2O-CF2CF2CF2O) x3 (CF2CF2O)-CF2CF2CF2-CH2OSO2CF3...(16C-1)

[0170] NMR spectrum of compound (16C-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 4.7 (2H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -56.3 (3F), -74.0 (3F), -84.0 (54F), -89.2 (54F), -91.4 (2F), -122.7 (2F), -123.6 (2F), -126.6 (52F). The average value of the number of units x3: 13, and the number average molecular weight of compound (16C-1): 4,830.

[0171] (Example 3-3) The same procedure as in Example 1-7 was repeated except that the amount of sodium hydride (55% / paraffin) was changed to 0.14 g, compound (16-1) was changed to compound (16C-1) obtained in Example 3-2, the amount of HOCH2C(CHOCH2CH=CH2)3 was changed to 0.95 g, and dilution with AK-225 was not performed after completion of the reaction. 3.9 g (yield 38%) of compound (17C-1) was obtained. CF3-O-(CF2CF2O-CF2CF2CF2CF2O) x3 (CF2CF2O)-CF2CF2CF2-CH2OCH2-C(CH2OCH2CH=CH2)3...(17C-1)

[0172] NMR spectrum of compound (17C-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.6 (6H), 3.7~3.9 (8H), 4.0 (2H), 5.1 (6H), 5.7~6.0 (3H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -56.3 (3F), -84.0 (54F), -89.2 (54F), -91.4 (2F), -120.5 (2F), -126.6 (52F), -128.6 (2F). The average value of the number of units x3: 13, and the number average molecular weight of compound (17C-1): 4,940.

[0173] (Example 3-4) The procedure was the same as in Example 1-8, except that compound (17-1) was replaced with 3.0 g of compound (17C-1) obtained in Example 3-3, the amount of platinum complex solution was 0.004 g, the amount of HSi(OCH3)3 was 0.40 g, the amount of dimethyl sulfoxide was 0.006 g, and the amount of 1,3-bis(trifluoromethyl)benzene (Tokyo Chemical Industry Co., Ltd.) was 0.30 g. The procedure was changed to 3.0 g (93% yield) of composition (3), consisting of compound (1C-1) in which the three allyl groups of compound (17C-1) were hydrosilylated, and a by-product in which some or all of the three allyl groups of compound (17C-1) were isomerized to inner olefins (-CH=CHCH3). The hydrosilylation conversion was 100%, and no compound (17C-1) remained. The hydrosilylation selectivity was 85%. CF3-O-(CF2CF2O-CF2CF2CF2CF2O) x3 (CF2CF2O)-CF2CF2CF2-CH2OCH2-C[CH2OCH2CH2CH2-Si(OCH3)3]3...(1C-1)

[0174] NMR spectrum of compound (1C-1); 1 H-NMR (300.4 MHz, solvent: CDCl3, standard: TMS) δ (ppm): 0.7 (6H), 1.7 (6H), 3.4-3.8 (44H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -56.3 (3F), -84.0 (54F), -89.2 (54F), -91.4 (2F), -120.5 (2F), -126.6 (52F), -128.6 (2F). The average value of the number of units x3: 13, and the number average molecular weight of compound (1C-1): 5,300.

[0175] [Example 4: Preparation of compound (1D-1)] (Example 4-1) A 200 mL recovery flask was charged with 10 g of HOCH2C(CH2CH=CH2)3, 20.0 g of 1,3-bis(trifluoromethyl)benzene (Tokyo Chemical Industry Co., Ltd.), and 25.5 g of (CF3SO2)2O. Under a nitrogen atmosphere, 19.3 g of 2,6-lutidine was added dropwise at 0°C. The mixture was heated to room temperature and stirred for 1 hour. After the reaction was complete, the organic phase was recovered by washing with water and concentrated using an evaporator. This was purified by silica gel column chromatography (eluent: hexane / ethyl acetate = 85 / 15 (mass ratio)) to obtain 15.1 g of compound (20) (yield 85%). CF3SO2OCH2C(CH2CH=CH2)3...(20)

[0176] NMR spectrum of compound (20); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 2.1 (6H), 4.3 (2H), 5.0~5.2 (6H), 5.6~5.8 (3H). 19 F-NMR (282.7MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -74.0 (3F).

[0177] (Example 4-2) The same procedure as in Example 1-7 was repeated, except that compound (16-1) was changed to 0.70 g of compound (20) obtained in Example 4-1 and HOCH2C(CH2OCH2CH═CH2)3 was changed to 10.0 g of compound (15-1) obtained in Example 1-5, to obtain 5.1 g of compound (17D-1) (yield 51%). CF3CF2CF2-O-(CF2CF2O)(CF2CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OCH2-C(CH2CH=CH2)3...(17D-1)

[0178] NMR spectrum of compound (17D-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 2.1 (6H), 3.7 (4H), 5.0~5.2 (6H), 5.8 (3H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.7 (42F), -77.2 (1F), -79.4 (1F), -82.2 (3F), -89.4 to -91.1 (90F), -130.5 (2F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (17D-1): 4,350.

[0179] (Example 4-3) Compound (17-1) was replaced by compound (17D-1) obtained in Example 4-2, and the amount of HSi(OCH3)3 was changed to 0.25 g. The procedure was the same as in Example 1-8, except that the three allyl groups of compound (17D-1) were hydrosilylated to obtain 1.9 g (yield 90%) of compound (1D-1). The hydrosilylation conversion was 100%, and no compound (17D-1) remained. The hydrosilylation selectivity was 100%, and no by-product was produced in which some or all of the three allyl groups of compound (17D-1) were isomerized to the inner olefin (-CH=CHCH3). CF3CF2CF2-O-(CF2CF2O)(CF2CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OCH2-C[CH2CH2CH2Si(OCH3)3]3...(1D-1)

[0180] NMR spectrum of compound (1D-1); 1 H-NMR (300.4 MHz, solvent: CDCl3, standard: TMS) δ (ppm): 0.7 (6H), 1.7 (6H), 3.4-3.8 (37H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.7 (42F), -77.2 (1F), -79.4 (1F), -82.2 (3F), -89.4 to -91.1 (90F), -130.5 (2F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (1D-1): 4,710.

[0181] Example 5: Preparation of compound (1E-1) (Example 5-1) The same procedure as in Example 1-7 was carried out except that compound (16-1) was changed to 0.72 g of compound (20) obtained in Example 4-1, HOCH2C(CH2OCH2CH═CH2)3 was changed to 10.0 g of compound (11-1) obtained in Example 1-1, and dilution with AK-225 was not performed after completion of the reaction. 5.0 g (yield 50%) of compound (17E-1) was obtained. CF3CF2CF2-O-CHFCF2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OCH2-C(CH2CH=CH2)3...(17E-1)

[0182] NMR spectrum of compound (17E-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 2.1 (6H), 3.7~3.9 (4H), 4.2 (2H), 5.0~5.2 (6H), 5.7~6.0 (4H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -51.2 to -54.6 (42F), -77.2 (1F), -77.7 (1F), -79.3 (1F), -79.7 (1F), -81.2 (3F), -84.3 to -87.2 (2F), -87.9 to -91.0 (82F), -129.4 (2F), -144.1 (1F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (17E-1): 4,300.

[0183] (Example 5-2) The procedure was the same as in Example 1-8, except that compound (17-1) was 1.8 g of compound (17E-1) obtained in Example 5-1 and the amount of HSi(OCH3)3 was changed to 0.23 g, and 1.7 g (87% yield) of compound (1E-1) was obtained in which the three allyl groups of compound (17E-1) were hydrosilylated. The hydrosilylation conversion was 100%, and no compound (17E-1) remained. The hydrosilylation selectivity was 100%, and no by-product in which some or all of the three allyl groups of compound (17E-1) were isomerized to the inner olefin (-CH=CHCH3) was produced. CF3CF2CF2-O-CHFCF2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OCH2-C[CH2CH2CH2-Si(OCH3)3]3...(1E-1)

[0184] NMR spectrum of compound (1E-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 0.7 (6H), 1.7 (6H), 3.4-3.8 (37H), 4.2 (2H), 5.8-6.0 (1H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -51.2 to -54.6 (42F), -77.2 (1F), -77.7 (1F), -79.3 (1F), -79.7 (1F), -81.2 (3F), -84.3 to -87.2 (2F), -87.9 to -91.0 (82F), -129.4 (2F), -144.1 (1F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (1E-1): 4,660.

[0185] Example 6: Preparation of compound (1F-1) (Example 6-1) Compound (16-1) was changed to 0.64 g of compound (20) obtained in Example 4-1, and HOCH2C(CH2OCH2CH=CH2)3 was changed to 10.0 g of compound (15C-1) obtained in Example 3-1. Except for not diluting with AK-225 after completion of the reaction, the same procedure as in Example 1-7 was carried out to obtain 4.9 g of compound (17F-1) (yield 48%). CF3-O-(CF2CF2O-CF2CF2CF2CF2O) x3 (CF2CF2O)-CF2CF2CF2-CH2OCH2-C(CH2CH=CH2)3...(17F-1)

[0186] NMR spectrum of compound (17F-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 2.1 (6H), 3.7~3.9 (4H), 5.0~5.2 (6H), 5.7~6.0 (3H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -56.3 (3F), -84.0 (54F), -89.2 (54F), -91.4 (2F), -120.5 (2F), -126.6 (52F), -128.6 (2F). The average value of the number of units x3: 13, and the number average molecular weight of compound (17F-1): 4,850.

[0187] (Example 6-2) Compound (17-1) was the compound (17F-1) obtained in Example 6-1, and the amount of HSi(OCH3)3 was changed to 0.23 g. The procedure was the same as in Example 1-8, with the exception that the three allyl groups of compound (17F-1) were hydrosilylated to obtain 1.9 g (yield 90%) of compound (1F-1). The hydrosilylation conversion was 100%, and no compound (17F-1) remained. The hydrosilylation selectivity was 100%, and no by-product was produced in which some or all of the three allyl groups of compound (17F-1) were isomerized to the inner olefin (-CH=CHCH3). CF3-O-(CF2CF2O-CF2CF2CF2CF2O) x3(CF2CF2O)-CF2CF2CF2-CH2OCH2-C[CH2CH2CH2-Si(OCH3)3]3...(1F-1)

[0188] NMR spectrum of compound (1F-1); 1 H-NMR (300.4 MHz, solvent: CDCl3, standard: TMS) δ (ppm): 0.7 (6H), 1.7 (6H), 3.4-3.8 (37H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -56.3 (3F), -84.0 (54F), -89.2 (54F), -91.4 (2F), -120.5 (2F), -126.6 (52F), -128.6 (2F). The average value of the number of units x3: 13, and the number average molecular weight of compound (1F-1): 5210.

[0189] [Example 7: Preparation of compound (2A-1)] (Example 7-1) The same procedure as in Example 1-6 was repeated, except that the amount of compound (15-1) was changed to 30.0 g of compound (10-1), the amount of 1,3-bis(trifluoromethyl)benzene (manufactured by Tokyo Chemical Industry Co., Ltd.) was changed to 30.0 g, the amount of CFSOCl (manufactured by Wako Pure Chemical Industries, Ltd.) was changed to 2.9 g, and the amount of triethylamine was changed to 3.0 g, to obtain 31.0 g (yield 97%) of compound (18-1). CF3SO2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OSO2CF3···(18-1)

[0190] NMR spectrum of compound (18-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 4.6 (2H). 19F-NMR (282.7 MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -51.2 to -54.6 (42F), -74.1 (6F), -77.0 (2F), -79.0 (2F), -87.5 to -91.0 (80F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (18-1): 4,150.

[0191] (Example 7-2) The same procedure as in Example 1-7 was conducted except that the amount of sodium hydride (55% / paraffin) was changed to 0.25 g, the amount of 1,3-bis(trifluoromethyl)benzene (Tokyo Chemical Industry Co., Ltd.) was changed to 10.0 g, compound (16-1) was changed to compound (18-1) obtained in Example 7-1, the amount of HOCH2C(CHOCH2CH=CH2)3 was changed to 1.6 g, and dilution with AK-225 was not performed after completion of the reaction. 1.5 g of compound (19-1) was obtained (yield 14%). (CH2=CHCH2OCH2)3C-CH2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OCH2-C(CH2OCH2CH=CH2)3...(19-1)

[0192] NMR spectrum of compound (19-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.6 (12H), 3.7~3.9 (20H), 5.1 (12H), 5.8 (6H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -51.2 to -54.6 (42F), -74.1 (6F), -77.3 (2F), -79.2 (2F), -87.5 to -91.0 (80F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (19-1): 4,360.

[0193] (Example 7-3) The procedure of Example 1-8 was repeated, except that compound (17-1) was replaced with 1.0 g of compound (19-1) obtained in Example 7-2 and the amount of HSi(OCH3)3 was changed to 0.40 g. This procedure yielded 1.1 g (96% yield) of composition (7), consisting of compound (2A-1) in which the six allyl groups of compound (19-1) were hydrosilylated, and a by-product in which some or all of the six allyl groups of compound (19-1) were isomerized to inner olefins (-CH=CHCH3). The hydrosilylation conversion was 100%, and no compound (19-1) remained. The hydrosilylation selectivity was 84%. [(CH3O)3Si-CH2CH2CH2OCH2]3C-CH2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OCH2-C[CH2OCH2CH2CH2-Si(OCH3)3]3...(2A-1)

[0194] NMR spectrum of compound (2A-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 0.7 (12H), 1.7 (12H), 3.4-3.8 (86H). 19 F-NMR (282.7MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -51.2~-54.6 (42F), -77.7 (2F), -79.7 (2F), -87.5~-91.0 (80F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (2A-1): 5,010.

[0195] [Example 8: Production of compound (4-1)] (Example 8-1) Compound (22-1) (21.5 g, yield 98%) was obtained in the same manner as in Example 1-6, except that compound (15-1) was changed to compound (21-1) (manufactured by Synquest Laboratories), the amount of CFSOCl (manufactured by Wako Pure Chemical Industries, Ltd.) was changed to 4.0 g, and the amount of triethylamine was changed to 4.5 g. CF3CF2CF2-O-(CF(CF3)CF2O) x4-CF(CF3)-CH2OH (21-1) CF3CF2CF2-O-(CF(CF3)CF2O) x4 -CF(CF3)-CH2OSO2CF3...(22-1)

[0196] NMR spectrum of compound (22-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 4.9 (2H). 19 F-NMR (282.7MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -74.2 (3F), -78.4~-82.2 (38F), -129.4 (2F), -135.0 (1F), -144.2 (6F). The average value of the number of units x 4: 6, and the number average molecular weight of compound (22-1): 1,440.

[0197] (Example 8-2) The same procedure as in Example 1-7 was repeated except that the amount of sodium hydride (55% / paraffin) was changed to 0.05 g, compound (16-1) was changed to compound (22-1) obtained in Example 8-1, the amount of HOCH2C(CHOCH2CH=CH2)3 was changed to 0.31 g, and dilution with AK-225 was not performed after completion of the reaction. 2.1 g (yield 20%) of compound (23-1) was obtained. CF3CF2CF2-O-(CF(CF3)CF2O) x4 -CF(CF3)-CH2OCH2-C(CH2OCH2CH=CH2)3...(23-1)

[0198] NMR spectrum of compound (23-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.6 (6H), 3.7~3.9 (8H), 4.0 (2H), 5.1 (6H), 5.8 (3H). 19 F-NMR (282.7MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -78.4~-82.2 (38F), -129.4 (2F), -132.0 (1F), -144.2 (6F). The average value of the number of units x 4: 6, and the number average molecular weight of compound (23-1): 1,550.

[0199] (Example 8-3) The procedure was repeated in Example 1-8, except that compound (17-1) was replaced with compound (23-1) obtained in Example 8-2, the amount of platinum complex solution was changed to 0.006 g, the amount of HSi(OCH3)3 was changed to 0.66 g, and the amount of dimethyl sulfoxide was changed to 0.01 g. This yielded 2.1 g (85% yield) of composition (8), consisting of compound (4-1) in which the three allyl groups of compound (23-1) were hydrosilylated, and a by-product in which some or all of the three allyl groups of compound (23-1) were isomerized to inner olefins (-CH=CHCH3). The hydrosilylation conversion was 100%, and no compound (23-1) remained. The hydrosilylation selectivity was 85%. CF3CF2CF2-O-(CF(CF3)CF2O) x4 -CF(CF3)-CH2OCH2-C[CH2OCH2CH2CH2-Si(OCH3)3]3...(4-1)

[0200] NMR spectrum of compound (4-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 0.7 (6H), 1.7 (6H), 3.4-3.8 (41H), 4.0 (2H). 19 F-NMR (282.7MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -78.4~-82.2 (38F), -129.4 (2F), -132.0 (1F), -144.2 (6F). The average value of the number of units x 4: 6, and the number average molecular weight of compound (4-1): 1,920.

[0201] Example 9: Preparation of compound (5-1) (Example 9-1) 20.0 g of compound (15-1) obtained in Example 1-5, 0.21 g of tetrabutylammonium hydrogen sulfate, 1.76 g of BrCH2CH═CH2, and 2.6 g of 30% aqueous sodium hydroxide solution were added to a 100 mL two-necked recovery flask and stirred at 60 °C for 8 hours. After the reaction was completed, 20 g of AC-2000 was added, washed once with dilute aqueous hydrochloric acid, and the organic phase was recovered. The recovered organic phase was passed through a silica gel column, and the recovered solution was concentrated using an evaporator to obtain 19.8 g of compound (24-1) (yield 98.2%). CF3CF2CF2-O-(CF2CF2O)(CF2CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OCH2CH=CH2···(24-1).

[0202] NMR spectrum of compound (24-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.7 (2H), 4.1 (2H), 5.2~5.3 (2H), 5.9 (1H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.3 to -55.7 (42F), -78.1 (1F), -80.1 (1F), -82.1 (3F), -89.4 to -91.1 (90F), -130.5 (2F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (24-1): 4,250.

[0203] (Example 9-2) Compound (17-1) was prepared by adding 5.0 g of compound (24-1) obtained in Example 9-1, 0.005 g of platinum complex solution, 0.25 g of HSi(OCH3)3, 0.005 g of dimethyl sulfoxide, 0.20 g of 1,3-bis(trifluoromethyl)benzene (Tokyo Chemical Industry Co., Ltd.), and 4 hours of reaction time. The procedure was the same as in Example 1-8, except that compound (17-1) was converted to compound (5-1) by hydrosilylation of one allyl group in compound (24-1), and a by-product in which one allyl group in compound (24-1) was isomerized to an inner olefin (-CH=CHCH3). 4.9 g (95% yield) of composition (9) was obtained. The hydrosilylation conversion was 100%, and no compound (24-1) remained. The hydrosilylation selectivity was 87%. CF3CF2CF2-O-(CF2CF2O)(CF2CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OCH2CH2CH2-Si(OCH3)3...(5-1)

[0204] NMR spectrum of compound (5-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 0.7 (6H), 1.7 (6H), 3.6 (11H), 3.8 (2H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -52.4 to -55.8 (42F), -78.2 (1F), -80.2 (1F), -82.2 (3F), -89.4 to -91.1 (90F), -130.5 (2F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (5-1): 4,370.

[0205] Example 10: Preparation of compound (5-2) (Example 10-1) Compound (15-1) was prepared by changing 52.0 g of compound (11-1) obtained in Example 1-1, the amount of tetrabutylammonium hydrogen sulfate to 0.52 g, the amount of BrCHCH=CH to 4.4 g, the amount of 30% aqueous sodium hydroxide solution to 6.5 g, and the amount of AC-2000 to 50 g, in the same manner as in Example 9-1, to obtain 52.4 g of compound (24-2) (yield 99.9%). CF3CF2CF2-O-CHFCF2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OCH2-CH=CH2...(24-2)

[0206] NMR spectrum of compound (24-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.7 (2H), 4.1 (2H), 4.2 (2H), 5.2~5.3 (2H), 5.8~6.0 (2H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.3 to -55.7 (42F), -78.1 (1F), -78.7 (1F), -80.2 (1F), -80.7 (1F), -82.2 (3F), -85.4 to -88.2 (2F), -89.4 to -91.1 (86F), -130.5 (2F), -145.1 (1F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (24-2): 4,190.

[0207] (Example 10-2) The procedure of Example 9-2 was repeated, except that compound (24-1) was replaced with compound (24-2) obtained in Example 10-1. This procedure yielded 4.8 g (93% yield) of composition (10), consisting of compound (5-2) in which one allyl group of compound (24-2) was hydrosilylated, and a by-product in which one allyl group of compound (24-2) was isomerized to an inner olefin (-CH=CHCH). The hydrosilylation conversion was 100%, and no compound (24-2) remained. The hydrosilylation selectivity was 85%. CF3CF2CF2-O-CHFCF2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OCH2CH2CH2-Si(OCH3)3...(5-2)

[0208] NMR spectrum of compound (5-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 0.7 (6H), 1.7 (6H), 3.6 (11H), 3.8 (2H), 4.2 (2H), 5.8~6.0 (1H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -52.3 to -55.7 (42F), -78.2 (1F), -78.7 (1F), -80.3 (1F), -80.7 (1F), -82.2 (3F), -85.4 to -88.2 (2F), -89.4 to -91.1 (82F), -130.5 (2F), -145.1 (1F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (5-2): 4,310.

[0209] Example 11: Preparation of compound (1I-1) (Example 11-1) Compound (14I-1) was obtained according to the method described in Example 6 of WO 2013 / 121984. CF3-O-(CF2CF2O-CF2CF2CF2CF2O) x3 (CF2CF2O)-CF2CF2CF2-C(O)OCH3...(14I-1)

[0210] NMR spectrum of compound (14I-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.9 (3H). 19F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -55.2 (3F), -82.1 (54F), -88.1 (54F), -90.2 (2F), -118.2 (2F), -125.4 (52F), -126.2 (2F). The average value of the number of units x3: 13, and the number average molecular weight of compound (14I-1): 4,700.

[0211] (Example 11-2) 9.0 g of compound (14I-1) obtained in Example 11-1 and 0.45 g of HN-CH-C(CHCH=CH) were placed in a 50 mL recovery flask and stirred for 12 hours. NMR confirmed that all of compound (14I-1) had been converted to compound (17I-1). Furthermore, methanol was produced as a by-product. The resulting solution was diluted with 9.0 g of AE-3000 and purified by silica gel column chromatography (developing solvent: AE-3000) to obtain 7.6 g of compound (17I-1) (yield 84%). CF3-O-(CF2CF2O-CF2CF2CF2CF2O) x3 (CF2CF2O)-CF2CF2CF2-C(O)NH-CH2-C(CH2CH=CH2)3...(17I-1)

[0212] NMR spectrum of compound (17I-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 2.1 (6H), 3.4 (2H), 5.2 (6H), 6.2~5.9 (3H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -55.2 (3F), -82.1 (54F), -88.1 (54F), -90.2 (2F), -119.6 (2F), -125.4 (52F), -126.2 (2F). The average value of the number of units x3: 13, and the number average molecular weight of compound (17I-1): 4,800.

[0213] (Example 11-3) A 10 mL PFA sample tube was charged with 6.0 g of compound (17I-1) obtained in Example 11-2, 0.07 g of a xylene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 2%), 0.78 g of HSi(OCH3)3, 0.02 g of dimethyl sulfoxide, and 0.49 g of 1,3-bis(trifluoromethyl)benzene (Tokyo Chemical Industry Co., Ltd.), and stirred for 10 hours at 40°C. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting mixture was filtered through a 1.0 μm pore membrane filter to obtain 6.7 g of compound (1I-1) (yield 100%). CF3-O-(CF2CF2O-CF2CF2CF2CF2O) x3 (CF2CF2O)-CF2CF2CF2-C(O)NH-CH2-C[CH2CH2CH2-Si(OCH3)3]3...(1I-1)

[0214] NMR spectrum of compound (1I-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 0.75 (6H), 1.3-1.6 (12H), 3.4 (2H), 3.7 (27H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -55.2 (3F), -82.1 (54F), -88.1 (54F), -90.2 (2F), -119.6 (2F), -125.4 (52F), -126.2 (2F). Average value of the number of units x3: 13, number average molecular weight of compound (1I-1): 5,400.

[0215] Example 12: Preparation of compound (1I-2) (Example 12-1) The procedure of Example 11-2 was repeated except that 0.41 g of H2N-C(CH2CH=CH2)3 was used instead of 0.45 g of H2N-CH2-C(CH2CH=CH2)3, to obtain 7.5 g of compound (17I-2) (yield 84%). CF3-O-(CF2CF2O-CF2CF2CF2CF2O) x3(CF2CF2O)-CF2CF2CF2-C(O)NH-C(CH2CH=CH2)3...(17I-2)

[0216] NMR spectrum of compound (17I-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 2.3 (6H), 5.2 (6H), 5.9~6.2 (3H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -55.2 (3F), -82.1 (54F), -88.1 (54F), -90.2 (2F), -119.4 (2F), -125.4 (52F), -126.2 (2F). The average value of the number of units x3: 13, and the number average molecular weight of the compound (17I-2): 4,800.

[0217] (Example 12-2) 6.7 g (100% yield) of compound (1I-2) was obtained in the same manner as in Example 11-3, except that compound (17I-2) obtained in Example 12-1 was used instead of compound (17I-1). CF3-O-(CF2CF2O-CF2CF2CF2CF2O) x3 (CF2CF2O)-CF2CF2CF2-C(O)NH-C[CH2CH2CH2-Si(OCH3)3]3...(1I-2)

[0218] NMR spectrum of compound (1I-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 0.75 (6H), 1.3-1.6 (12H), 3.7 (27H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -55.2 (3F), -82.1 (54F), -88.1 (54F), -90.2 (2F), -119.4 (2F), -125.4 (52F), -126.2 (2F). The average value of the number of units x3: 13, and the number average molecular weight of compound (1I-2): 5,400.

[0219] Example 13: Preparation of compound (1H-1) (Example 13-1) According to the method described in J. Org. Chem., Vol. 64, 1999, pp. 2564-2566, the compound (11-1) obtained in Example 1-1 was oxidized to obtain the compound (13H-1). CF3CF2CF2-O-CHFCF2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-C(O)OH (13H-1)

[0220] NMR spectrum of compound (13H-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 4.2 (2H), 5.8~6.0 (1H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.8 (42F), -78.8 (2F), -80.5 (1F), -80.8 (1F), -82.2 (3F), -85.3 to -88.2 (2F), -89.4 to -91.1 (82F), -130.5 (2F), -145.1 (1F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (13H-1): 4,150.

[0221] (Example 13-2) 6.2 g of compound (13H-1) obtained in Example 13-1 and 20 mL of methanol were placed in a 50 mL recovery flask and stirred at room temperature for 12 hours. NMR confirmed that all of compound (13H-1) had been converted to compound (14H-1). The solvent was distilled off under reduced pressure to obtain 6.2 g of compound (14H-1) (yield 100%). CF3CF2CF2-O-CHFCF2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-C(O)OCH3···(14H-1)

[0222] NMR spectrum of compound (14H-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.9 (3H), 4.2 (2H), 5.8~6.0 (1H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.8 (42F), -77.8 (1F), -78.8 (1F), -79.5 (1F), -80.8 (1F), -82.2 (3F), -85.3 to -88.2 (2F), -89.4 to -91.1 (82F), -130.5 (2F), -145.1 (1F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (14H-1): 4,150.

[0223] (Example 13-3) Compound (17H-1) (4.8 g, yield 76%) was obtained in the same manner as in Example 11-2, except that compound (14I-1) was changed to 5.7 g of compound (14H-1) obtained in Example 13-2 and the amount of H2N-CH2-C(CH2CH=CH2)3 was changed to 0.26 g. CF3CF2CF2-O-CHFCF2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-C(O)NH-CH2-C(CH2CH=CH2)3...(17H-1)

[0224] NMR spectrum of compound (17H-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 2.2 (6H), 3.3 (2H), 3.5 (1H), 4.2 (2H), 5.2 (6H), 5.8~6.0 (4H). 19F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.8 (42F), -78.8 (2F), -79.6 (1F), -80.8 (1F), -82.2 (3F), -85.3 to -88.2 (2F), -89.4 to -91.1 (82F), -130.5 (2F), -145.1 (1F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (17H-1): 4,250.

[0225] (Example 13-4) The same procedure as in Example 11-3 was repeated, except that compound (17I-1) was changed to 3.5 g of compound (17H-1) obtained in Example 13-3, the amount of platinum complex solution was changed to 0.03 g, the amount of HSi(OCH3)3 was changed to 0.5 g, the amount of dimethyl sulfoxide was changed to 0.01 g, and the amount of 1,3-bis(trifluoromethyl)benzene (manufactured by Tokyo Chemical Industry Co., Ltd.) was changed to 0.35 g, to obtain 3.8 g of compound (1H-1) (yield 100%). CF3CF2CF2-O-CHFCF2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-C(O)NH-CH2-C[CH2CH2CH2-Si(OCH3)3]3...(1H-1)

[0226] NMR spectrum of compound (1H-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 0.75 (6H), 1.3~1.6 (12H), 3.4 (2H), 3.7 (27H), 5.8~6.0 (1H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.8 (42F), -78.8 (2F), -79.6 (1F), -80.8 (1F), -82.2 (3F), -85.3 to -88.2 (2F), -89.4 to -91.1 (82F), -130.5 (2F), -145.1 (1F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (1H-1): 4,600.

[0227] Example 14: Preparation of compound (1H-2) (Example 14-1) The procedure of Example 13-3 was repeated except that 0.24 g of H2N-C(CH2CH=CH2)3 was used instead of 0.26 g of H2N-CH2-C(CH2CH=CH2)3, to obtain 4.7 g of compound (17H-2) (yield 80%). CF3CF2CF2-O-CHFCF2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-C(O)NH-C(CH2CH=CH2)3...(17H-2)

[0228] NMR spectrum of compound (17H-2); 1 H-NMR (300.4 MHz, solvent: CDCl3, standard: TMS) δ (ppm): 2.4 (6H), 3.5 (1H), 5.2 (6H), 5.8-6.0 (4H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.8 (42F), -78.8 (2F), -79.6 (1F), -80.8 (1F), -82.2 (3F), -85.3 to -88.2 (2F), -89.4 to -91.1 (82F), -130.5 (2F), -145.1 (1F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (17H-2): 4,250.

[0229] (Example 14-2) The same procedure as in Example 13-4 was carried out except that compound (17H-1) was changed to compound (17H-2) obtained in Example 14-1, to give 3.8 g of compound (1H-2) (yield 100%). CF3CF2CF2-O-CHFCF2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-C(O)NH-C[CH2CH2CH2-Si(OCH3)3]3...(1H-2)

[0230] NMR spectrum of compound (1H-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 0.75 (6H), 1.3~1.7 (12H), 3.4 (2H), 3.7 (27H), 5.8~6.0 (1H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.8 (42F), -78.8 (2F), -79.6 (1F), -80.8 (1F), -82.2 (3F), -85.3 to -88.2 (2F), -89.4 to -91.1 (82F), -130.5 (2F), -145.1 (1F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (1H-2): 4,600.

[0231] Example 15: Preparation of compound (1K-1) (Example 15-1) A 50 mL recovery flask was charged with 1.0 g of CF2=CFOCF2CF2CF2-C(O)OCH3 and 0.55 g of H2N-CH2-C(CH2CH=CH2)3 and stirred for 12 hours. NMR analysis confirmed that all of the CF2=CFOCF2CF2CF2-C(O)OCH3 had been converted to compound (30-1). The by-product methanol was also formed. The resulting solution was diluted with 6.0 g of AE-3000 and purified by silica gel column chromatography (developing solvent: AE-3000) to obtain 1.3 g of compound (30-1) (84% yield). CF2=CFOCF2CF2CF2-C(O)NH-CH2-C(CH2CH=CH2)3...(30-1)

[0232] NMR spectrum of compound (30-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 2.1 (6H), 3.4 (2H), 5.2 (6H), 5.9~6.2 (3H). 19F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -84.2 (2F), -113.4 to 114.2 (1F), -119.5 (2F), -121.1 to -121.9 (1F), -125.3 (2F), -134.5 to -135.3 (1F).

[0233] (Example 15-2) In a 50 mL recovery flask, 1.0 g of compound (30-1) obtained in Example 15-1, 10 g of compound (11-1) obtained in Example 1-1, 2 g of 48% by mass potassium hydroxide aqueous solution, and 0.1 g of (CH3)3COH were added and stirred at 60°C for 5 hours. NMR confirmed that all of compound (11-1) had been converted to compound (17K-1). 20 g of 1N hydrochloric acid was added to the resulting solution, and after confirming that the aqueous layer was acidic, the organic layer was separated and the solvent was distilled off, yielding 11 g of compound (17K-1) (yield 100%). CF3CF2CF2-O-CHFCF2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2CH2OCF2CHFOCF2CF2CF2-C(O)NH-CH2-C(CH2CH=CH2)3...(17K-1)

[0234] NMR spectrum of compound (17K-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 2.2 (6H), 3.3 (2H), 3.5 (1H), 4.2 (4H), 5.2 (6H), 5.8~6.0 (5H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.8 (42F), -78.8 (2F), -79.6 (1F), -80.8 (1F), -82.2 (3F), -84.2 (2F), -85.3 to -88.2 (2F), -89.4 to -91.1 (82F), -119.5 (2F), -125.3 (2F), -130.5 (4F), -145.1 (2F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (17K-1): 4,520.

[0235] (Example 15-3) The same procedure as in Example 11-3 was repeated, except that compound (17I-1) was changed to 5 g of compound (17K-1) obtained in Example 15-2, the amount of platinum complex solution was changed to 0.5 mg, the amount of HSi(OCH3)3 was changed to 0.5 g, the amount of dimethyl sulfoxide was changed to 0.01 g, and the amount of 1,3-bis(trifluoromethyl)benzene (manufactured by Tokyo Chemical Industry Co., Ltd.) was changed to 0.2 g, to obtain 5.4 g of compound (1K-1) (yield 100%). CF3CF2CF2-O-CHFCF2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2CH2OCF2CHFOCF2CF2CF2-C(O)NH-CH2-C[CH2CH2CH2-Si(OCH3)3]3...(1K-1)

[0236] NMR spectrum of compound (1K-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 0.75 (6H), 1.3~1.6 (12H), 3.3 (2H), 3.5 (27H), 4.2 (4H), 5.8~6.0 (2H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.8 (42F), -78.8 (2F), -79.6 (1F), -80.8 (1F), -82.2 (3F), -84.2 (2F), -85.3 to -88.2 (2F), -89.4 to -91.1 (82F), -119.5 (2F), -125.3 (2F), -130.5 (4F), -145.1 (2F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (1K-1): 4,950.

[0237] Example 16: Preparation of compound (1G-1) (Example 16-1) Compound (14-1) was obtained according to the method described in Example 4 of WO 2014 / 163004. CF3CF2CF2-O-(CF2CF2O)(CF2CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-C(O)OCH3···(14-1)

[0238] NMR spectrum of compound (14-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 3.9 (3H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.8 (42F), -82.2 (3F), -89.4 to -91.1 (92F), -130.5 (2F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (14-1): 4,230.

[0239] (Example 16-2) Compound (17G-1) (4.4 g, yield 85%) was obtained in the same manner as in Example 11-2, except that compound (14I-1) was changed to 5.0 g of compound (14-1) obtained in Example 16-1 and the amount of HN-CH-C(CHCH=CH) was changed to 0.2 g. CF3CF2CF2-O-(CF2CF2O)(CF2CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-C(O)NH-CH2-C(CH2CH=CH2)3...(17G-1)

[0240] NMR spectrum of compound (17G-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 2.2 (6H), 3.3 (2H), 3.5 (1H), 5.2 (6H), 5.8~6.0 (3H). 19F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.8 (42F), -82.2 (3F), -89.4 to -91.1 (92F), -130.8 (2F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (17G-1): 4,360.

[0241] (Example 16-3) The same procedure as in Example 11-3 was repeated, except that compound (17I-1) was changed to 4 g of compound (17G-1) obtained in Example 16-2, the amount of platinum complex solution was changed to 0.4 mg, the amount of HSi(OCH3)3 was changed to 0.33 g, the amount of dimethyl sulfoxide was changed to 0.01 g, and the amount of 1,3-bis(trifluoromethyl)benzene (manufactured by Tokyo Chemical Industry Co., Ltd.) was changed to 0.2 g, to obtain 4.3 g of compound (1G-1) (yield 100%). CF3CF2CF2-O-(CF2CF2O)(CF2CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-C(O)NH-CH2-C[CH2CH2CH2-Si(OCH3)3]3...(1G-1)

[0242] NMR spectrum of compound (1G-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 0.75 (6H), 1.3-1.6 (12H), 3.4 (2H), 3.7 (27H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.8 (42F), -82.2 (3F), -89.4 to -91.1 (92F), -130.8 (2F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (1G-1): 4,720.

[0243] Example 48: Preparation of compound (1D-2) (Example 48-1) A 50 mL three-neck flask was charged with 3.0 g of pentaerythritol (Kanto Chemical Co., Ltd.), 7.4 g of 48% aqueous NaOH, and 10.8 g of dimethyl sulfoxide. The mixture was heated to 60°C, 11.5 g of 5-bromo-1-pentene (Tokyo Chemical Industry Co., Ltd.) was added, and the mixture was stirred for 4 hours. The mixture was washed once with dilute aqueous hydrochloric acid, and 16 g of cyclopentyl methyl ether (Kanto Chemical Co., Ltd.) was added. The organic phase was recovered. The recovered solution was concentrated using an evaporator to obtain 6.1 g of crude product. The crude product was developed using silica gel column chromatography (eluent: hexane / ethyl acetate = 90 / 10 (mass ratio)) to obtain 3.7 g of HOCH2C(CHOCH2CH2CH2CH=CH2)3 (49% yield).

[0244] (Example 48-2) In a 50 mL recovery flask, 3.0 g of HOCH2C(CHOCH2CH2CH2CH=CH2)3 obtained in Example 48-1, 9.0 g of AE-3000, and 1.4 g of 2,6-lutidine were placed, and 3.8 g of (CF3SO2)2O was added dropwise at 0°C under a nitrogen atmosphere. The mixture was warmed to room temperature and stirred for 1 hour. After the reaction was completed, the organic phase was recovered by washing with water and concentrated using an evaporator. This was purified by silica gel column chromatography (developing solvent: AE-3000) to obtain 4.2 g of compound (20-2) (yield 99%). CF3SO2OCH2C(CH2OCH2CH2CH2CH=CH2)3...(20-2)

[0245] NMR spectrum of compound (20-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 1.6 (6H), 2.0 (6H), 3.4 (12H), 4.5 (2H), 5.0 (6H), 5.8 (3H). 19 F-NMR (282.7MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -75.0 (3F).

[0246] (Example 48-3) In a 25 mL recovery flask, 8.9 g of compound (15-1) obtained in Example 1-5, 1.0 g of compound (20-2) obtained in Example 48-2, 11 g of 1,3-bis(trifluoromethyl)benzene, and 1.4 g of cesium carbonate were placed and stirred at 80 °C for 8 hours under a nitrogen atmosphere. After the reaction was completed, the organic phase was recovered by washing with water and concentrated using an evaporator. This was purified by silica gel column chromatography (developing solvent: AE-3000, followed by AE-3000 / ethyl acetate = 9 / 1 (mass ratio)) to obtain 8.2 g of compound (17D-2) (yield 85%). CF3CF2CF2-O-(CF2CF2O)(CF2CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OCH2-C(CH2OCH2CH2CH2CH=CH2)3...(17D-2)

[0247] NMR spectrum of compound (17D-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 1.6 (6H), 2.1 (6H), 3.4 (6H), 3.5 (6H), 3.7 (2H), 3.9 (2H), 4.8~5.0 (6H), 5.8 (3H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.4 to -55.7 (42F), -77.2 (1F), -79.4 (1F), -82.2 (3F), -89.4 to -91.1 (90F), -130.5 (2F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (17D-2): 4,540.

[0248] (Example 48-4) The procedure of Example 1-8 was repeated, except that compound (17-1) was replaced with compound (17D-2) obtained in Example 48-3, and 2.1 g (yield 97%) of compound (1D-2) was obtained by hydrosilylating the three vinyl groups of compound (17D-2). The hydrosilylation conversion was 100%, and no compound (17D-2) remained. The hydrosilylation selectivity was 100%, and no by-product was produced in which some or all of the three vinyl groups of compound (17D-2) were isomerized to the inner olefin (-CH=CHCH). CF3CF2CF2-O-(CF2CF2O)(CF2CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OCH2-C[CH2OCH2CH2CH2CH2CH2Si(OCH3)3]3...(1D-2)

[0249] NMR spectrum of compound (1D-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 0.7 (6H), 1.4-1.6 (18H), 3.4 (6H), 3.5 (6H), 3.6 (27H), 3.7 (2H), 3.9 (2H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: CFCl3) δ (ppm): -52.3 to -55.6 (42F), -77.2 (1F), -79.4 (1F), -82.2 (3F), -89.4 to -91.0 (90F), -130.5 (2F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (1D-2): 4,900.

[0250] Example 49: Preparation of compound (1E-2) (Example 49-1) 7.9 g (yield 83%) of compound (17E-2) was obtained in the same manner as in Example 48-3, except that compound (15-1) was changed to 8.8 g of compound (11-1) obtained in Example 1-1. CF3CF2CF2-O-CHFCF2OCH2-(CF2O){(CF2O) x1 (CF2CF2O)x2}-CF2-CH2OCH2-C(CH2OCH2CH2CH2CH=CH2)3...(17E-2)

[0251] NMR spectrum of compound (17E-1); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ(ppm): 1.6(6H), 2.1(6H), 3.4(6H), 3.5(6H), 3.7(2H), 3.9(2H), 4.2(2H), 4.8~5.0(6H), 5.8~6.0(4H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -51.2 to -54.6 (42F), -77.2 (1F), -77.7 (1F), -79.3 (1F), -79.7 (1F), -81.2 (3F), -84.3 to -87.2 (2F), -87.9 to -91.0 (82F), -129.4 (2F), -144.1 (1F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (17E-1): 4,490.

[0252] (Example 49-2) The procedure of Example 1-8 was repeated, except that compound (17D-2) was replaced with compound (17E-2) obtained in Example 49-1, and 2.0 g (yield 92%) of compound (1E-2) was obtained by hydrosilylating the three vinyl groups of compound (17E-2). The hydrosilylation conversion was 100%, and no compound (17E-2) remained. The hydrosilylation selectivity was 100%, and no by-product was produced in which some or all of the three vinyl groups of compound (17E-2) were isomerized to the inner olefin (-CH=CHCH3). CF3CF2CF2-O-CHFCF2OCH2-(CF2O){(CF2O) x1 (CF2CF2O) x2}-CF2-CH2OCH2-C[CH2OCH2CH2CH2CH2CH2-Si(OCH3)3]3...(1E-2)

[0253] NMR spectrum of compound (1E-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ(ppm): 0.7(6H), 1.4-1.6(18H), 3.4(6H), 3.5(6H), 3.6(27H), 3.7(2H), 3.9(2H), 4.2(2H), 5.8-6.0(1H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -51.2 to -54.6 (42F), -77.2 (1F), -77.7 (1F), -79.3 (1F), -79.7 (1F), -81.2 (3F), -84.3 to -87.2 (2F), -87.9 to -91.0 (82F), -129.4 (2F), -144.1 (1F). Average value of number of units x1: 21, average value of number of units x2: 20, number average molecular weight of compound (1E-2): 4,850.

[0254] Example 50: Preparation of compound (1F-2) (Example 50-1) The same procedure as in Example 48-3 was carried out except that the compound (15-1) was changed to 9.9 g of the compound (15C-1) obtained in Example 3-1, and 8.8 g of the compound (17F-2) was obtained (yield 83%). CF3-O-(CF2CF2O-CF2CF2CF2CF2O) x3 (CF2CF2O)-CF2CF2CF2-CH2OCH2-C(CH2OCH2CH2CH2CH=CH2)3...(17F-2)

[0255] NMR spectrum of compound (17F-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 1.6 (6H), 2.1 (6H), 3.4 (6H), 3.5 (6H), 3.7 (2H), 3.9 (2H), 4.8~5.0 (6H), 5.8 (3H). 19F-NMR (282.7 MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -56.3 (3F), -84.0 (54F), -89.2 (54F), -91.4 (2F), -120.5 (2F), -126.6 (52F), -128.6 (2F). The average value of the number of units x3: 13, and the number average molecular weight of compound (17F-2): 5,040.

[0256] (Example 50-2) The procedure of Example 1-8 was repeated, except that compound (17D-2) was replaced with compound (17F-2) obtained in Example 50-1, and the three vinyl groups of compound (17F-2) were hydrosilylated to obtain 2.1% (yield 98%) of compound (1F-2). The hydrosilylation conversion was 100%, and no compound (17F-2) remained. The hydrosilylation selectivity was 100%, and no by-product was produced in which some or all of the three vinyl groups of compound (17F-2) were isomerized to the inner olefin (-CH=CHCH3). CF3-O-(CF2CF2O-CF2CF2CF2CF2O) x3 (CF2CF2O)-CF2CF2CF2-CH2OCH2-C[CH2OCH2CH2CH2CH2CH2-Si(OCH3)3]3...(1F-2)

[0257] NMR spectrum of compound (1F-2); 1 H-NMR (300.4MHz, solvent: CDCl3, standard: TMS) δ (ppm): 0.7 (6H), 1.4-1.6 (18H), 3.4 (6H), 3.5 (6H), 3.6 (27H), 3.7 (2H), 3.9 (2H). 19 F-NMR (282.7 MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -56.3 (3F), -84.0 (54F), -89.2 (54F), -91.4 (2F), -120.5 (2F), -126.6 (52F), -128.6 (2F). The average value of the number of units x3: 13, and the number average molecular weight of compound (1F-1): 5,400.

[0258] [Examples 17-32 and 51-53: Manufacturing and Evaluation of Articles] The substrates were surface treated using the compounds or compositions obtained in Examples 1 to 16 and 48 to 50, to obtain articles in Examples 17 to 32 and 51 to 53. The surface treatment methods used in each example were the dry coating method and the wet coating method described below. Chemically strengthened glass was used as the substrate. The obtained articles were evaluated by the following methods. The results are shown in Tables 1 to 4.

[0259] (Dry coating method) Dry coating was carried out using a vacuum deposition apparatus (VTR-350M, manufactured by ULVAC Corporation) (vacuum deposition method). 0.5 g of each of the compounds or compositions obtained in Examples 1 to 16 and 48 to 50 was placed in a molybdenum boat in the vacuum deposition apparatus, and the interior of the vacuum deposition apparatus was heated to 1×10 -3 The boat containing the composition was heated at a rate of 10°C / min or less, and when the deposition rate measured by a quartz crystal oscillator film thickness meter exceeded 1 nm / sec, the shutter was opened to start film formation on the surface of the substrate. When the film thickness reached approximately 50 nm, the shutter was closed to terminate film formation on the surface of the substrate. The substrate on which the composition had been deposited was heat-treated at 200°C for 30 minutes and washed with AK-225 to obtain an article having a surface-treated layer on the surface of the substrate.

[0260] (wet coating method) Each compound or composition obtained in Examples 1 to 16 and 48 to 50 was mixed with C4F9OC2H5 (3M, Novec (registered trademark) 7200) as a liquid medium to prepare a coating solution with a solids concentration of 0.05%. A substrate was dipped into the coating solution, left for 30 minutes, and then pulled out (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-treated layer on the surface of the substrate.

[0261] (Evaluation method) <Contact angle measurement method> 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 points on the surface of the surface layer, and the average value was calculated. The 2θ method was used to calculate the contact angle.

[0262] <Initial contact angle> The surface layer was measured for the initial water contact angle and the initial n-hexadecane contact angle by the above-mentioned measurement method, and the evaluation criteria were as follows. Initial water contact angle: ◎ (Excellent): Over 115 degrees. ○ (Good): 110 degrees or more but less than 115 degrees. △ (Acceptable): 100 degrees or more but less than 110 degrees. × (Not acceptable): Less than 100 degrees. Initial n-hexadecane contact angle: ◎ (Excellent): Over 66 degrees. ○ (Good): 65 degrees or more but less than 66 degrees. △ (Acceptable): 63 degrees or more but less than 65 degrees. × (Not acceptable): Less than 63 degrees.

[0263] <Abrasion resistance> The surface layer was measured for its water contact angle after 10,000 strokes of steel wool Bonstar (#0000) at a pressure of 98.07 kPa and a speed of 320 cm / min using a reciprocating traverse tester (KNT Corporation) in accordance with JIS L0849:2013 (ISO 105-X12:2001). The smaller the decrease in water repellency (water contact angle) after rubbing, 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 10,000 reciprocating strokes is 5 degrees or less. ○ (Good): The change in water contact angle after 10,000 reciprocating strokes is more than 5 degrees and 10 degrees or less. △ (Acceptable): The change in water contact angle after 10,000 reciprocating strokes is more than 10 degrees and less than 20 degrees. × (Unacceptable): The change in water contact angle after 10,000 reciprocating strokes is more than 20 degrees.

[0264] <Appearance> The haze of the article was measured using a haze meter (manufactured by Toyo Seiki Co., Ltd.). The smaller the haze, the more uniformly the fluorine-containing ether compound was applied, and the better the appearance. The evaluation criteria were as follows: ◎ (Excellent): Haze is 0.1% or less. ○ (Good): Haze is more than 0.1% and 0.2% or less. △ (Acceptable): Haze is over 0.2% and 0.3% or less. × (unacceptable): Haze is over 0.3%.

[0265] <Fingerprint removal> A fingerprint stamp was prepared by applying artificial fingerprint liquid (a liquid consisting of oleic acid and squalene) to the flat surface of a silicone rubber stopper and then wiping off excess oil with a nonwoven fabric (Bencotto (registered trademark) M-3, manufactured by Asahi Kasei Corporation). The fingerprint stamp was placed on the surface layer and pressed with a load of 9.8 N for 10 seconds. The haze of the fingerprint-adhered area was measured with a haze meter and recorded as the initial value. The fingerprint-adhered area was wiped with a reciprocating traverse tester (manufactured by KNT Corporation) equipped with tissue paper at a load of 4.9 N. The haze value was measured after each wiping stroke, and the number of wiping strokes required to reduce the haze to 10% or less of the initial value was counted. The fewer the wiping strokes, the easier it was to remove fingerprint stains and the better the fingerprint stain wiping ability. The evaluation criteria are as follows. ◎ (Excellent): Wiping required 3 times or less. ○ (Good): Wiping was performed 4 to 5 times. △ (Acceptable): Wipe 6 to 8 times. × (Not acceptable): Wiping more than 9 times.

[0266] <Light resistance> The surface layer was subjected to a tabletop xenon arc lamp accelerated light resistance test (SUNTEST XLS+, manufactured by Toyo Seiki Co., Ltd.) at a black panel temperature of 63°C and exposed to light (650 W / m 2 After 500 hours of irradiation with light (300 to 700 nm), the water contact angle was measured. The smaller the decrease in water contact angle after the accelerated light resistance test, the smaller the deterioration in performance due to light and the more excellent the light resistance. The evaluation criteria are as follows. ◎ (Excellent): The change in water contact angle after the accelerated light resistance test is 5 degrees or less. ○ (Good): The change in water contact angle after the accelerated light resistance test was more than 5 degrees and 10 degrees or less. △ (Acceptable): The change in water contact angle after the accelerated light resistance test is more than 10 degrees and 20 degrees or less. × (unacceptable): The change in water contact angle after the accelerated light resistance test is more than 20 degrees.

[0267] <Lubricity> The dynamic friction coefficient of the surface layer against artificial skin (PBZ13001, manufactured by Idemitsu Technofine Co., Ltd.) was measured using a load-varying friction and wear testing system (HHS2000, manufactured by Shinto Scientific Co., Ltd.) under conditions of contact area: 3 cm x 3 cm, load: 0.98 N. The smaller the dynamic friction coefficient, the better the lubricity. The evaluation criteria are as follows: ◎ (Excellent): Coefficient of dynamic friction is 0.3 or less. ○ (Good): Coefficient of dynamic friction is greater than 0.3 and equal to or less than 0.4. △ (Acceptable): Coefficient of dynamic friction is greater than 0.4 and less than 0.5. × (Not acceptable): Coefficient of dynamic friction is over 0.5.

[0268] [Table 1]

[0269] [Table 2]

[0270] [Table 3]

[0271] [Table 4]

[0272] Examples 17 to 22, 27 to 32, and 51 to 53, which used the present compound having three hydrolyzable silyl groups at one end or a composition containing the present compound, were excellent in water and oil repellency, abrasion resistance, appearance, fingerprint stain removability, light resistance, and lubricity. In Example 23, which used a composition containing a compound (2A-1) having three hydrolyzable silyl groups at both ends, the abrasion resistance, appearance, fingerprint removability, and lightfastness were poor. The reason for the poor fingerprint wiping ability is thought to be that unreacted terminal groups reduce the surface properties. The reason for the poor appearance and abrasion resistance is thought to be due to a decrease in uniformity caused by aggregation of the non-fluorine moieties at the ends. The reason for the poor abrasion resistance is thought to be due to both ends being fixed to the substrate. In Example 24, which used a composition containing compound (4-1) in which the poly(oxyperfluoroalkylene) chain had a branched structure, the lubricity was significantly reduced due to the reduced molecular mobility caused by the branched structure, which is thought to have been one of the reasons why the friction resistance also significantly decreased. In Examples 25 and 26, in which compositions containing compound (5-1) or compound (5-2) having only one hydrolyzable silyl group at one end were used, the abrasion resistance and light resistance were poor.

[0273] [Examples 33-47: Manufacture and evaluation of articles] The compound (3A-1) isolated in Example 1-1 was prepared. The composition containing the compound (1B-1) obtained in Example 2-3 was purified to obtain the compound (1B-1). The composition containing the compound (2A-1) obtained in Example 7-3 was purified to obtain the compound (2A-1).

[0274] Compositions were prepared by mixing Compound (1B-1), Compound (2A-1), and Compound (3A-1) in the proportions shown in Table 5. Each composition was used to manufacture an article by the wet coating method described above. The articles were subjected to measurement of contact angle and evaluation of abrasion resistance and lubricity. The results are shown in Table 5.

[0275] [Table 5]

[0276] From Examples 33 to 37, it was found that when compound (2A-1) having three hydrolyzable silyl groups at both ends was added to the present compound having three hydrolyzable silyl groups at one end, the surface layer had practical performance as long as the proportion of compound (2A-1) was less than 40 mass%. As the proportion of compound (2A-1) increased, the friction resistance and lubricity tended to decrease. From Examples 38 to 42, it was found that when the compound (3A-1) having no hydrolyzable silyl groups at both ends was added to the present compound having three hydrolyzable silyl groups at one end, the surface layer had practical performance as long as the proportion of compound (3A-1) was less than 40 mass %. As the proportion of compound (3A-1) increased, the abrasion resistance tended to decrease. From Examples 43 to 47, it was found that when a compound (2A-1) having three hydrolyzable silyl groups at both ends and a compound (3A-1) having no hydrolyzable silyl groups at both ends were simultaneously added to the present compound having three hydrolyzable silyl groups at one end, the surface layer had practical performance as long as the total proportion of compound (2A-1) and compound (3A-1) was less than 40 mass%. As the total proportion of compound (2A-1) and compound (3A-1) increased, the abrasion resistance tended to decrease. [Industrial Applicability]

[0277] The fluorine-containing ether compound of the present invention can be suitably used for surface treatment to impart water and oil repellency to the surface of a substrate such as a member constituting the surface of a touch panel that is touched by fingers. The entire contents of the specification, claims and abstract of Japanese Patent Application No. 2015-171986, filed on September 1, 2015, are hereby incorporated by reference as part of the disclosure of the present invention.

Claims

1. A compound represented by the following formula (14) and H ２ N-R １１ -C(CH ２ CH=CH ２ ) ３ and a compound represented by the following formula (17G) obtained by reacting HSiR １３ ｎ１ X １ ３－ｎ１ A method for producing a compound represented by the following formula (1G): A １ -O-(CF ２ CF ２ O)(CF ２ CF ２ O)(R Ｆ１ O) ｘ -CF ２ -C(O)OR １０ ・・・(14) A １ -O-(CF ２ CF ２ O)(CF ２ CF ２ O)(R Ｆ１ O) ｘ -CF ２ -C(O)NH-R １１ -C(CH ２ CH=CH ２ ) ３ ・・・(17G) A １ -O-(CF ２ CF ２ O)(CF ２ CF ２ O)(R Ｆ１ O) ｘ -CF ２ -C(O)NH-R １１ -C[CH ２ CH ２ CH ２ -SiR １３ ｎ１ X １ ３－ｎ１ ] ３ ・・・(1G) however, A １ is a perfluoroalkyl group having 1 to 20 carbon atoms, R Ｆ１ is a perfluoroalkylene group having no branched structure, x is an integer from 1 to 198; R １０ is an alkyl group, R １１ represents a single bond, an alkylene group, or the C(CH ２ CH=CH ２ ) ３ a group having an etheric oxygen atom at the terminal bonding to the alkylene group having two or more carbon atoms and an etheric oxygen atom between carbon atoms, or a C(CH ２ CH=CH ２ ) ３ a group having an etheric oxygen atom at the end bonding to the carbon atom and between the carbon atoms, (R Ｆ１ O) ｘ R is the same or two or more types Ｆ１ O, R １３ is a hydrogen atom or a monovalent hydrocarbon group, X １ is an alkoxy group, a halogen atom, an acyl group, or an isocyanate group (—NCO), n1 is an integer of 0 to 2.

2. A compound represented by the following formula (14H) and H ２ N-R １１ -C(CH ２ CH=CH ２ ) ３ and a compound represented by the following formula (17H) obtained by reacting HSiR １３ ｎ１ X １ ３－ｎ１ A method for producing a compound represented by the following formula (1H): A １ -O-CHFCF ２ OCH ２ -(CF ２ O)(R Ｆ１ O) ｘ -CF ２ -C(O)OR １０ ・・・(1HH) A １ -O-CHFCF ２ OCH ２ -(CF ２ O)(R Ｆ１ O) ｘ -CF ２ -C(O)NH-R １１ -C(CH ２ CH=CH ２ ) ３ ・・・(17H) A １ -O-CHFCF ２ OCH ２ -(CF ２ O)(R Ｆ１ O) ｘ -CF ２ -C(O)NH-R １１ -C[CH ２ CH ２ CH ２ -SiR １３ ｎ１ X １ ３－ｎ１ ] ３ ・・・(1H) however, A １ is a perfluoroalkyl group having 1 to 20 carbon atoms, R Ｆ１ is a perfluoroalkylene group having no branched structure, x is an integer from 1 to 198; R １０ is an alkyl group, R １１ represents a single bond, an alkylene group, or the C(CH ２ CH=CH ２ ) ３ a group having an etheric oxygen atom at the terminal bonding to the alkylene group having two or more carbon atoms and an etheric oxygen atom between carbon atoms, or a C(CH ２ CH=CH ２ ) ３ is a group having an etheric oxygen atom at the end bonding to and between carbon atoms, (R Ｆ１ O) ｘ R is the same or two or more types Ｆ１ O, R １３ is a hydrogen atom or a monovalent hydrocarbon group, X １ is an alkoxy group, a halogen atom, an acyl group, or an isocyanate group (—NCO), n1 is an integer of 0 to 2.

3. A compound represented by the following formula (14I) and H ２ N-R １１ -C(CH ２ CH=CH ２ ) ３ and a compound represented by the following formula (17I) obtained by reacting HSiR １３ ｎ１ X １ ３－ｎ１ A method for producing a compound represented by the following formula (1I): A １ -O-(R Ｆ１ O) ｘ -Q １２ -C(O)OR １０ ・・・(14I) A １ -O-(R Ｆ１ O) ｘ -Q １２ -C(O)NH-R １１ -C(CH ２ CH=CH ２ ) ３ ・・・(17I) A １ -O-(R Ｆ１ O) ｘ -Q １２ -C(O)NH-R １１ -C[CH ２ CH ２ CH ２ -SiR １３ ｎ１ X １ ３－ｎ１ ] ３ ・・・(1I) however, A １ is a perfluoroalkyl group having 1 to 20 carbon atoms, R Ｆ１ is a perfluoroalkylene group having no branched structure, x is an integer from 1 to 198; Q １２ is a perfluoroalkylene group having no branched structure, R １０ is an alkyl group, R １１ represents a single bond, an alkylene group, or the C(CH ２ CH=CH ２ ) ３ a group having an etheric oxygen atom at the terminal bonding to the alkylene group having two or more carbon atoms and an etheric oxygen atom between carbon atoms, or a C(CH ２ CH=CH ２ ) ３ is a group having an etheric oxygen atom at the end bonding to and between carbon atoms, (R Ｆ１ O) ｘ R is the same or two or more types Ｆ１ O, R １３ is a hydrogen atom or a monovalent hydrocarbon group, X １ is an alkoxy group, a halogen atom, an acyl group, or an isocyanate group (—NCO), n1 is an integer of 0 to 2.

4. a compound represented by the following formula (17J) obtained by reacting a compound represented by the following formula (15) with a compound represented by the following formula (30) in the presence of a basic compound; and HSiR １３ ｎ１ X １ ３－ｎ１ A method for producing a compound represented by the following formula (1J): A １ -O-(CF ２ CF ２ O)(CF ２ CF ２ O)(R Ｆ１ O) ｘ -CF ２ -CH ２ OH ・・・(15) CF ２ =CFOCF ２ CF ２ CF ２ -C(O)NH-R １１ -C(CH ２ CH=CH ２ ) ３ ・・・(30) A １ -O-(CF ２ CF ２ O)(CF ２ CF ２ O)(R Ｆ１ O) ｘ -CF ２ CH ２ OCF ２ CHFOCF ２ CF ２ CF ２ -C(O)NH-R １１ -C(CH ２ CH=CH ２ ) ３ ・・・(17J) A １ -O-(CF ２ CF ２ O)(CF ２ CF ２ O)(R Ｆ１ O) ｘ -CF ２ CH ２ OCF ２ CHFOCF ２ CF ２ CF ２ -C(O)NH-R １１ -C[CH ２ CH ２ CH ２ -SiR １３ ｎ１ X １ ３－ｎ１ ] ３ ・・・(1J) however, A １ is a perfluoroalkyl group having 1 to 20 carbon atoms, R Ｆ１ is a perfluoroalkylene group having no branched structure, x is an integer from 1 to 198; R １１ represents a single bond, an alkylene group, or the C(CH ２ CH=CH ２ ) ３ a group having an etheric oxygen atom at the terminal bonding to the alkylene group having two or more carbon atoms and an etheric oxygen atom between carbon atoms, or a C(CH ２ CH=CH ２ ) ３ a group having an etheric oxygen atom at the end bonding to the carbon atom and between the carbon atoms, (R Ｆ１ O) ｘ R is the same or two or more types Ｆ１ It consists of O, R １３ is a hydrogen atom or a monovalent hydrocarbon group, X １ is an alkoxy group, a halogen atom, an acyl group, or an isocyanate group (—NCO), n1 is an integer of 0 to 2.

5. a compound represented by the following formula (17K) obtained by reacting a compound represented by the following formula (11) with a compound represented by the following formula (30) in the presence of a basic compound; and HSiR １３ ｎ１ X １ ３－ｎ１ A method for producing a compound represented by the following formula (1K): A １ -O-CHFCF ２ OCH ２ -(CF ２ O)(R Ｆ１ O) ｘ -CF ２ -CH ２ OH ・・・(11) CF ２ =CFOCF ２ CF ２ CF ２ -C(O)NH-R １１ -C(CH ２ CH=CH ２ ) ３ ・・・(30) A １ -O-CHFCF ２ OCH ２ -(CF ２ O)(R Ｆ１ O) ｘ -CF ２ CH ２ OCF ２ CHFOCF ２ CF ２ CF ２ -C(O)NH-R １１ -C(CH ２ CH=CH ２ ) ３ ・・・(17K) A １ -O-CHFCF ２ OCH ２ -(CF ２ O)(R Ｆ１ O) ｘ -CF ２ CH ２ OCF ２ CHFOCF ２ CF ２ CF ２ -C(O)NH-R １１ -C[CH ２ CH ２ CH ２ -SiR １３ ｎ１ X １ ３－ｎ１ ] ３ ・・・(1K) however, A １ is a perfluoroalkyl group having 1 to 20 carbon atoms, R Ｆ１ is a perfluoroalkylene group having no branched structure, x is an integer from 1 to 198; R １１ represents a single bond, an alkylene group, or the C(CH ２ CH=CH ２ ) ３ a group having an etheric oxygen atom at the terminal bonding to the alkylene group having two or more carbon atoms and an etheric oxygen atom between carbon atoms, or a C(CH ２ CH=CH ２ ) ３ a group having an etheric oxygen atom at the end bonding to the carbon atom and between the carbon atoms, (R Ｆ１ O) ｘ R is the same or two or more types Ｆ１ O, R １３ is a hydrogen atom or a monovalent hydrocarbon group, X １ is an alkoxy group, a halogen atom, an acyl group, or an isocyanate group (—NCO), n1 is an integer of 0 to 2.

6. a compound represented by the following formula (17L) obtained by reacting a compound represented by the following formula (15C) with a compound represented by the following formula (30) in the presence of a basic compound; and HSiR １３ ｎ１ X １ ３－ｎ１ A method for producing a compound represented by the following formula (1L): A １ -O-(R Ｆ１ O) ｘ -R Ｆ CH ２ OH ・・・(15C) CF ２ =CFOCF ２ CF ２ CF ２ -C(O)NH-R １１ -C(CH ２ CH=CH ２ ) ３ ・・・(30) A １ -O-(R Ｆ１ O) ｘ -R Ｆ CH ２ OCF ２ CHFOCF ２ CF ２ CF ２ -C(O)NH-R １１ -C(CH ２ CH=CH ２ ) ３ ・・・(17L) A １ -O-(R Ｆ１ O) ｘ -R Ｆ CH ２ OCF ２ CHFOCF ２ CF ２ CF ２ -C(O)NH-R １１ -C[CH ２ CH ２ CH ２ -SiR １３ ｎ１ X １ ３－ｎ１ ] ３ ・・・(1L) however, A １ is a perfluoroalkyl group having 1 to 20 carbon atoms, R Ｆ１ is a perfluoroalkylene group having no branched structure, R Ｆ is a perfluoroalkylene group having no branched structure, x is an integer from 1 to 198; R １１ represents a single bond, an alkylene group, or the C(CH ２ CH=CH ２ ) ３ a group having an etheric oxygen atom at the terminal bonding to the alkylene group having two or more carbon atoms and an etheric oxygen atom between carbon atoms, or a C(CH ２ CH=CH ２ ) ３ is a group having an etheric oxygen atom at the end bonding to and between carbon atoms, (R Ｆ１ O) ｘ R is the same or two or more types Ｆ１ O, R １３ is a hydrogen atom or a monovalent hydrocarbon group, X １ is an alkoxy group, a halogen atom, an acyl group, or an isocyanate group (—NCO), n1 is an integer of 0 to 2.

Images