Surface treatment agent, surface treatment agent composition, coating liquid, article, and method for manufacturing article

Abstract

Provided are: a fluorine-containing ether compound, a fluorine-containing ether composition, and a coating liquid that are capable of forming a surface layer having excellent durability; an article having a surface layer that has excellent durability and that can maintain water and oil repellency, lubricity, and fingerprint removability for a long period of time; and a manufacturing method for said article.　The present invention provides a fluorine-containing ether compound having: a polyfluoropolyether chain; a reactive silyl group; and a linking group that contains a group represented by *-O-C(=O)-** and that links the polyfluoropolyether chain, which is positioned on the * side, and the reactive silyl group, which is positioned on the ** side.

Description

[Technical Field]

[0001] The present invention relates to a fluorinated ether compound, a surface treatment agent, a fluorinated ether composition, a coating liquid, an article, and a method for producing an article. [Background technology]

[0002] Fluorine-containing ether compounds having a fluoropolyether chain and a hydrolyzable silyl group have attracted attention because they can impart excellent water and oil repellency, abrasion resistance, low fingerprint adhesion, fingerprint smudge removability, and lubricity to the surface of a substrate. Since these fluorine-containing ether compounds can form a surface layer exhibiting these properties on the surface of a substrate, they are suitable for use in surface treatment agents.

[0003] For example, Patent Document 1 proposes a fluorine-containing ether compound having a perfluoropolyether chain and a hydrolyzable silyl group as a fluorine-containing ether compound that has excellent fingerprint stain removal properties and can form a durable surface layer on the surface of a substrate. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] International Publication No. 2017 / 038832 Summary of the Invention [Problem to be solved by the invention]

[0005] The fluorine-containing ether compounds and the like described in Patent Document 1 are said to have high abrasion resistance. However, there is an increasing demand for even greater abrasion resistance, and there is a need for surface treatment agents that exhibit even better abrasion resistance.

[0006] The present invention aims to provide a fluorinated ether compound, a surface treatment agent, a fluorinated ether composition and a coating liquid which are capable of forming a surface layer having excellent durability, an article having a surface layer having excellent durability and capable of maintaining water and oil repellency, lubricity and fingerprint stain removability for a long period of time, and a method for producing the same. [Means for solving the problem]

[0007] The present invention provides a fluorine-containing compound having the following constitutions [1] to [9] and a method for producing the same, a surface treatment agent, a fluorine-containing compound-containing composition, a coating liquid, an article, and a method for producing the same. [1] A polyfluoropolyether chain and a reactive silyl group, a linking group containing a group represented by *-OC(=O)-** and linking the polyfluoropolyether chain located on the * side with the reactive silyl group located on the ** side; A fluorine-containing ether compound having the formula: [2] The linking group is *-R 1 The fluorine-containing ether compound according to [1], which contains a group represented by —O—C(═O)—**. however, R 1 is an alkylene group having 1 to 10 carbon atoms which may have a substituent (excluding a fluorine atom). [3] A fluorine-containing ether compound represented by the following formula 1. R f [-R 1 -OC(=O)-Q 1 {-T} g ] j formula 1 however, R f is R 1 and at least one fluorine atom is bonded to the carbon atom bonded to R 1 is an alkylene group having 1 to 10 carbon atoms which may have a substituent (excluding a fluorine atom), and the plurality of R 1 may be the same or different, Q 1is a (g+1)-valent organic group having a carbon atom or nitrogen atom bonded to —O—C(═O)— in formula 1, and Q 1 If there are multiple Qs, 1 may be the same or different, T is -Si(R) 3-a (L) a When there are two or more T's, the two or more T's may be the same or different, R is an alkyl group, L is a hydrolyzable group or a hydroxyl group, and two or more Ls in T may be the same or different; a is 2 or 3, g is an integer of 1 or more, and when there are multiple g's, the multiple g's may be the same or different, j is 1 or 2. [4] Q 1 The fluorine-containing ether compound according to [3], wherein the compound is represented by any one of the following formulae (Q1) to (Q7): [ka] -A 1 -C(R e2 ) 3-g3 (-Q 22 -) g3 Formula (Q2) -A 2 -N(-Q 23 -)2 equation (Q3) -A 3 -Z 1 (-Q 24 -) g4 Formula (Q4) -A 2 -Si(R e3 ) 3-g3 (-Q 25 -) g3 Formula (Q5) -A 1 -Q 26 - Formula (Q6) -A 1 -CH(-Q 22 -)-Si(R e3 ) 3-g5 (-Q 25 -)g5 Formula (Q7) However, in formulas (Q1) to (Q7), A 1 , A 2 or A 3 The side connects to -OC(=O)- in formula 1, and Q 22 , Q 23 , Q 24 , Q 25 or Q 26 The side connects to the T, A 1 represents a single bond, an alkylene group, or an alkylene group having two or more carbon atoms with -C(O)NR between carbon atoms. e6 -, -C(O)-, -NR e6 - or -O-, A 2 represents an alkylene group or an alkylene group having two or more carbon atoms with -C(O)NR between carbon atoms. e6 -, -C(O)-, -NR e6 - or -O-, A 3 is A 3 Z bonded to 1 If the atom in is a carbon atom, then A 1 and A 3 Z binds to 1 If the atom in is a nitrogen atom, A 2 and Q 11 represents a single bond, -O-, an alkylene group, or -C(O)NR between carbon atoms of an alkylene group having two or more carbon atoms. e6 -, -C(O)-, -NR e6 - or -O-, Q 22 is an alkylene group, an alkylene group with two or more carbon atoms that has -C(O)NR between carbon atoms. e6 -, -C(O)-, -NR e6 a group having - or -O-, and -C(O)NR at the end of the alkylene group not connected to T e6 -, -C(O)-, -NR e6 A group having - or -O-, or an alkylene group having 2 or more carbon atoms having -C(O)NR between carbon atoms. e6 -, -C(O)-, -NR e6- or -O- and -C(O)NR at the end not connected to T e6 -, -C(O)-, -NR e6 - or -O-, and Q 1 Q 22 If there are two or more, there are two or more Q 22 may be the same or different, Q 23 represents an alkylene group or an alkylene group having two or more carbon atoms with -C(O)NR between carbon atoms. e6 -, -C(O)-, -NR e6 - or -O-, and two Q 23 may be the same or different, Q 24 Q 24 Z binds to 1 If the atom in is a carbon atom, then Q 22 and Q 24 Z binds to 1 If the atom in is a nitrogen atom, Q 23 and Q 1 Q 24 If there are two or more, there are two or more Q 24 may be the same or different, Q 25 represents an alkylene group or an alkylene group having two or more carbon atoms with -C(O)NR between carbon atoms. e6 -, -C(O)-, -NR e6 - or -O-, and Q 1 Q 25 If there are two or more, there are two or more Q 25 may be the same or different, Q 26 represents an alkylene group or an alkylene group having two or more carbon atoms with -C(O)NR between carbon atoms. e6 -, -C(O)-, -NR e6 - or -O-, Z 1 is A 3 has a carbon atom or nitrogen atom to which Q is directly bonded, 24 has a carbon atom or nitrogen atom directly bonded to it (g 4 a group having a +1)valent ring structure, R e1 is a hydrogen atom or an alkyl group, and Q 1 R e1 If there are two or more, there are two or more R e1 may be the same or different, R e2 is a hydrogen atom, a hydroxyl group, an alkyl group, or an acyloxy group, R e3 is an alkyl group, R e6 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group, g1 is an integer of 0 to 3, g2 is an integer of 0 to 3, and g1+g2 is an integer of 1 to 6; g3 is an integer from 1 to 3, g4 is an integer equal to or greater than 1, g5 is an integer from 0 to 3. [5] A surface treatment agent containing any one of the fluorine-containing ether compounds [1] to [4]. [6] A fluorinated ether composition comprising at least one fluorinated ether compound according to any one of [1] to [4] and another fluorinated ether compound. [7] A fluorinated ether compound according to any one of [1] to [4] or a fluorinated ether composition according to [6], A coating liquid containing a liquid medium. [8] Any of the fluorine-containing ether compounds [1] to [4] or [6] An article having a surface layer formed from a fluorinated ether composition. [9] The fluorinated ether compound according to any one of [1] to [4], the fluorinated ether composition according to [6], or the 7 A method for manufacturing an article, comprising forming a surface layer by a dry coating method or a wet coating method using a coating liquid of the formula (1). [Effects of the Invention]

[0008] The present invention provides a fluorinated ether compound, a surface treatment agent, a fluorinated ether composition and a coating liquid which are capable of forming a surface layer having excellent durability, an article having a surface layer which is excellent in durability and which can maintain water and oil repellency, lubricity and fingerprint stain removability for a long period of time, and a method for producing the same. [Brief explanation of the drawings]

[0009] [Figure 1] 1 is a schematic cross-sectional view showing an example of an article of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0010] As used herein, the following terms have the following meanings: In this specification, the compound represented by formula 1A will be referred to as compound 1A. Compounds represented by other formulas will also be referred to in the same manner. Furthermore, a group represented by formula g1a will be referred to as group g1a. Groups represented by other formulas will be similarly referred to. "Oxyfluoro(cyclo)alkylene" is a general term for oxyfluoroalkylene and oxyfluorocycloalkylene. The term "reactive silyl group" is a general term for a hydrolyzable silyl group and a silanol group (Si-OH). The term "hydrolyzable silyl group" refers to a group that can undergo a hydrolysis reaction to form a silanol group. The term "surface layer" refers to a layer formed on the surface of a substrate. When the fluorine-containing ether compound is a mixture of a plurality of fluorine-containing ether compounds having different chain lengths of the polyfluoropolyether chain, the "molecular weight" of the polyfluoropolyether chain is 1 H-NMR and 19 It is the number average molecular weight calculated by F-NMR to determine the number (average value) of oxyfluoro(cyclo)alkylene units based on the terminal groups. The symbol "to" indicating a range of values ​​means that the values ​​before and after it are included as the lower and upper limits.

[0011] [Fluorine-containing ether compounds] The fluorine-containing ether compound of the present invention (hereinafter also referred to as "the compound") is characterized by having a polyfluoropolyether chain, a reactive silyl group, and a linking group containing a group represented by *-OC(=O)-**, and having a structure in which the polyfluoropolyether chain located on the * side and the reactive silyl group located on the ** side are linked via the linking group.

[0012] The present compound has a polyfluoropolyether chain. The present compound having a polyfluoropolyether chain is excellent in removing fingerprint stains from the surface layer. In this compound, the oxygen atom of the ester bond contained in the linking group is positioned on the polyfluoropolyether chain side, thereby suppressing the hydrolysis reaction of the ester moiety, resulting in a compound with excellent chemical stability.

[0013] The polyfluoropolyether chain is a group having two or more oxyfluoro(cyclo)alkylene units. Examples of the polyfluoropolyether chain include R f1 The polyfluoropolyether chain is preferably a perfluoropolyether chain, since it provides the surface layer with even better abrasion resistance and fingerprint removability.

[0014] The polyfluoropolyether chain in the present invention may have a fluorine-containing ring structure which may have a heteroatom. In the case of a monovalent polyfluoropolyether chain, it has either or both of a monovalent fluorine-containing ring structure at a free end and a divalent fluorine-containing ring structure in the middle of the main chain. In the case of a divalent polyfluoropolyether chain, it has a divalent fluorine-containing ring structure in the middle of the main chain. The polyfluoropolyether chain has a fluorine-containing ring structure, which provides excellent chemical resistance and various durability properties such as light resistance. The fluorine-containing ring structure is preferably a 3- to 8-membered ring in view of ease of production of the present compound, more preferably a 4- to 6-membered ring in view of further improving the abrasion resistance and slip resistance of the surface layer, and particularly preferably a 4-membered ring. Details of the ring structure will be described later. Here, the "free end" means an end of the polyfluoropolyether chain to which no reactive silyl group is bonded via a linking group. Also, the "monovalent fluorine-containing alicyclic structure at a free end" means a ring structure in which one of the carbon atoms constituting the fluorine-containing alicyclic ring is a carbon atom at the end of the main chain of the polyfluoropolyether chain that is not bonded to a linking group.

[0015] The linking group is, among others, *-R 1 A group represented by -OC(=O)-** (where R 1 It is preferable that R is an alkylene group having 1 to 10 carbon atoms which may have a substituent other than a fluorine atom. When the carbon atom bonded to the oxygen atom side of the ester bond does not have a fluorine atom, chemical stability is improved and hydrolysis reactions are suppressed. 1 The alkylene group in R is preferably an alkylene group having 1 to 6 carbon atoms, more preferably an alkylene group having 1 to 3 carbon atoms, further preferably a methylene group or an ethylene group, and particularly preferably a methylene group. 1 Examples of the substituent that may be contained in the alkyl group include an alkyl group that may have a hetero atom, an aryl group, an alkoxy group, and a hydroxyl group. The alkyl group is preferably an alkyl group having 1 to 6 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, an n-butyl group, a tert-butyl group, and a cyclohexyl group. Examples of heteroatoms that may be present between carbon atoms of the alkyl group include an oxygen atom, a nitrogen atom, a sulfur atom, and a silicon atom. The alkyl group may further have a substituent. Examples of the substituent that the alkyl group may have include a halogen atom, a hydroxyl group, a hydrolyzable silyl group, and an aryl group. Examples of the aryl group include carbon rings such as phenyl and naphthyl groups, and heterocyclic rings such as pyridyl groups. Examples of the substituent that the aryl group may have include halogen atoms, hydroxyl groups, hydrolyzable silyl groups, and alkyl groups. Examples of the hydrolyzable silyl group include the same as those in T described below. R 1As the alkylene group, a straight-chain alkylene group having no substituent is preferred from the viewpoints of chemical stability and ease of production.

[0016] The present compound preferably has a structure represented by the following formula 1, since it has excellent chemical stability and can provide a surface layer that can maintain water and oil repellency, lubricity, and fingerprint stain removability for a long period of time. R f [-R 1 -OC(=O)-Q 1 {-T} g ] j formula 1 however, R f is R 1 and at least one fluorine atom is bonded to the carbon atom bonded to R 1 is an alkylene group having 1 to 10 carbon atoms which may have a substituent (excluding a fluorine atom), and the plurality of R 1 may be the same or different, Q 1 is a (g+1)-valent organic group having a carbon atom bonded to —O—C(═O)— in formula 1, and Q 1 If there are multiple Qs, 1 may be the same or different, T is -Si(R) 3-a (L) a When there are two or more T's, the two or more T's may be the same or different, R is an alkyl group, L is a hydrolyzable group or a hydroxyl group, and two or more Ls in T may be the same or different; a is 2 or 3, g is an integer of 1 or more, and when there are multiple g's, the multiple g's may be the same or different, j is 1 or 2.

[0017] The compound represented by formula 1 (Compound 1) is a compound having a structure of "monovalent polyfluoropolyether chain-linking group-reactive silyl group" (when j=1) or a compound having a structure of "reactive silyl group-linking group-divalent polyfluoropolyether chain-linking group-reactive silyl group" (when j=2). Compound 1 has a reactive silyl group at at least one end. This compound with a reactive silyl group at the end bonds strongly to the substrate, resulting in excellent abrasion resistance of the surface layer.

[0018] When j=1, Formula 1 is expressed by the following Formula 1A. When j=2, Formula 1 is expressed by the following Formula 1B. R fa -R 1 -OC(=O)-Q 1 {-T} g formula 1A {T} g -Q 1 -C(=O)-OR 1 -R fb -R 1 -OC(=O)-Q 1 {-T} g Formula 1B However, R fa is a monovalent polyfluoropolyether chain, and R fb are divalent polyfluoropolyether chains, and both are the same as R in Formula 1. f The other symbols are the same as those in Equation 1.

[0019] R fa is a monovalent polyfluoropolyether chain. fa As the chain, a monovalent perfluoropolyether chain is more preferred in terms of providing a surface layer with even better abrasion resistance and fingerprint stain removability. R fb is a divalent polyfluoropolyether chain. fb As the chain, a divalent perfluoropolyether chain is more preferred in terms of providing a surface layer with even better abrasion resistance and fingerprint stain removability. The molecular weight of the monovalent or divalent polyfluoropolyether chain is preferably 50 to 1,000, more preferably 100 to 900, and particularly preferably 200 to 800, from the viewpoint of achieving both fingerprint removability and slip resistance of the surface layer, and from the viewpoint of chemical resistance. If the molecular weight of the polyfluoropolyether chain is at least the lower limit of the above range, the fingerprint removability of the surface layer will be even better. If the molecular weight of the polyfluoropolyether chain is at most the upper limit of the above range, the slip resistance of the surface layer will be even better. The molecular weight of the polyfluoropolyether chain is preferably 1500 to 10000, more preferably 2000 to 8000, and particularly preferably 2500 to 6000, from the viewpoints of further improving the abrasion resistance and fingerprint removability of the surface layer, and of chemical resistance. If the molecular weight of the polyfluoropolyether chain is at least the lower limit of the above range, the abrasion resistance and fingerprint removability of the surface layer will be further improved. If the molecular weight of the polyfluoropolyether chain is not more than the upper limit of the above range, the abrasion resistance of the surface layer will be further improved.

[0020] R fa Examples of the group include group g1a. R f1 -(OR f2 ) m1 -(O) n1 - formula g1a However, R f1 R is a fluoroalkyl group having 1 to 20 carbon atoms or a monovalent fluorinated hydrocarbon group having a fluorine-containing alicyclic structure. f2 is a fluoroalkylene group having 1 to 6 carbon atoms or a divalent fluorinated hydrocarbon group having a fluorine-containing alicyclic structure. m1 is an integer of 0 to 500, and when m1 is 2 or more, (OR f2 ) m1 is two or more types of OR f2 n1 is 0 or 1.

[0021] R fb Examples of the group g1b include a group having a group g1b. The group g1b has one or more fluorine-containing alicyclic structures. -(R f3 ) n2 -(OR f2 )m2 -(O) n3 - formula g1b However, R f2 and R f3 are each independently a fluoroalkylene group having 1 to 6 carbon atoms or a divalent fluorinated hydrocarbon group having a fluorine-containing alicyclic structure. m2 is an integer of 0 to 500, and when m2 is 2 or greater, (OR f2 ) m is two or more types of OR f2 n2 and n3 each independently represent 0 or 1, provided that n2+m2 is 1 or greater.

[0022] R f1 If the fluoroalkyl group has 1 to 20 carbon atoms, the surface layer will have even better abrasion resistance and fingerprint removability. f1 The number of carbon atoms in the fluoroalkyl group is preferably 1 to 6, more preferably 1 to 4, and particularly preferably 1 to 3, in order to further improve the abrasion resistance and fingerprint stain removability of the surface layer. R f1 The fluoroalkyl group R is preferably a perfluoroalkyl group, since it provides the surface layer with even better abrasion resistance and fingerprint removability. f1 Compound 1A in which is a perfluoroalkyl group has a terminal CF3-. Compound 1A having a terminal CF3- can form a surface layer with low surface energy, and therefore the abrasion resistance and fingerprint removability of the surface layer are further improved. R f1 Examples of the fluoroalkyl group include CF3-, CF3CF2-, CF3CF2CF2-, CF3CF2CF2CF2-, CF3CF2CF2CF2CF2-, CF3CF2CF2CF2CF2CF2-, and CF3CF(CF3)-.

[0023] R f1 The number of carbon atoms in the monovalent fluorinated hydrocarbon group having a fluorinated alicyclic structure is preferably from 3 to 20, more preferably from 4 to 8, and particularly preferably from 4 to 6. When the number of carbon atoms in the fluorinated hydrocarbon group is within the above range, the surface layer has even better abrasion resistance and fingerprint removability. R f1As the fluorinated hydrocarbon group, a fluorocycloalkyl group is preferred in that the surface layer has better slip resistance. R f1 The fluorinated hydrocarbon group is preferably a completely fluorinated hydrocarbon group, since this provides the surface layer with even better abrasion resistance and fingerprint removability. R f1 Examples of the fluorinated hydrocarbon group include the monovalent fluorine-containing aliphatic ring structures exemplified in the above formula.

[0024] R f2 or R f3 If the fluoroalkylene group has 1 to 6 carbon atoms, the surface layer will have even better abrasion resistance and fingerprint removability. R f2 or R f3 The fluoroalkylene group is preferably a straight-chain fluoroalkylene group, since this provides the surface layer with even better abrasion resistance and fingerprint removability. R f2 or R f3 The fluoroalkylene group is preferably a perfluoroalkylene group, since this provides the surface layer with even better abrasion resistance and fingerprint removability. All R f2 The proportion of perfluoroalkylene groups in the above is preferably 60 mol % or more, more preferably 80 mol % or more, and particularly preferably 100 mol %, in order to further improve the abrasion resistance and fingerprint removability of the surface layer.

[0025] R f2 or R f3 The number of carbon atoms in the divalent fluorinated hydrocarbon group having a fluorinated alicyclic structure is preferably from 3 to 20, more preferably from 4 to 8, and particularly preferably from 4 to 6. When the number of carbon atoms in the fluorinated hydrocarbon group is within the above range, the surface layer has even better abrasion resistance and fingerprint removability. R f2 or R f3 As the fluorinated hydrocarbon group, a fluorocycloalkylene group is preferred in that the surface layer has better slip resistance. R f2 or R f3The fluorinated hydrocarbon group is preferably a completely fluorinated hydrocarbon group, since this provides the surface layer with even better abrasion resistance and fingerprint removability. R f2 or R f3 Examples of the fluorinated hydrocarbon group include the divalent fluorine-containing aliphatic ring structures exemplified in the above formula.

[0026] When sufficient slip resistance is required for the surface layer, m1 or m2 is preferably an integer from 0 to 30, more preferably an integer from 0 to 20, and particularly preferably an integer from 0 to 10. When m1 or m2 is equal to or less than the upper limit of the above range, the slip resistance of the surface layer is further improved. When sufficient abrasion resistance and fingerprint removability are required for the surface layer, m1 or m2 is preferably an integer of 2 to 200, more preferably an integer of 5 to 150, and particularly preferably an integer of 10 to 100. When m1 or m2 is equal to or greater than the lower limit of the above range, the abrasion resistance and fingerprint removability of the surface layer are even more excellent. When m1 or m2 is equal to or less than the upper limit of the above range, the abrasion resistance of the surface layer is even more excellent. In other words, when the number-average molecular weights of Compound 1A and Compound 1B are too large, the number of hydrolyzable silyl groups present per unit molecular weight decreases, and the abrasion resistance of the surface layer decreases. n1, n2, and n3 are R 1 This determines whether the end of the polyfluoropolyether chain that bonds to R is a carbon atom or an oxygen atom, and each may be 0 or 1. Among these, from the viewpoint of ease of production, R 1 It is preferable that the end of the polyfluoropolyether chain that bonds to n1 is a carbon atom. That is, n1 is preferably 0, n2 is preferably 1, and n3 is preferably 0.

[0027] OR f2Among these, examples of the linear or branched oxyfluoroalkylene unit include OCHF, OCF2CHF, OCHFCF2, OCF2CH2, OCH2CF2, OCF2CF2CHF, OCHFCF2CF2, OCF2CF2CH2, OCH2CF2CF2, OCF2CF2CF2CH2, OCH2CF2CF2CF2CF2, OCF2CF2CF2CF2CH2, OCH2CF2CF2CF2CF2, OCF2CF2CF2CF2CH2, OCH2CF2CF2CF2CF2CF2, OCF2, OCF2CF2, OCF2CF2CF2CF2, OCF(CF3)CF2, OCF2CF2CF2CF2, OCF(CF3)CF2CF2, OCF2CF2CF2CF2CF2, and OCF2CF2CF2CF2CF2CF2.

[0028] OR f2 Among these, an oxyfluorocycloalkylene unit can be mentioned, where * in the formula indicates a bond.

[0029] [ka]

[0030] (OR f2 ) m1 AND (OR f2 ) m2 When two or more kinds of oxyfluoro(cyclo)alkylene units are present, the bonding order of the oxyfluoro(cyclo)alkylene units is not limited. For example, when OCF2 and OCF2CF2 are present, OCF2 and OCF2CF2 may be arranged randomly, alternately, or in blocks. The presence of two or more types of oxyfluoro(cyclo)alkylene units means that there are two or more types of oxyfluoro(cyclo)alkylene units with different numbers of carbon atoms, there are two or more types of oxyfluoro(cyclo)alkylene units with different numbers of hydrogen atoms, there are two or more types of oxyfluoro(cyclo)alkylene units with different positions of hydrogen atoms, and there are two or more types of oxyfluoro(cyclo)alkylene units with the same number of carbon atoms but different in the presence or absence of side chains or the type of side chain (the number of side chains, the number of carbon atoms in the side chain, etc.). The arrangement of two or more oxyfluoro(cyclo)alkylene units is, for example, {(OCF2) m3 (OCF2CF2) m4 The structure represented by} indicates that m3 (OCF2) and m4 (OCF2CF2) are randomly arranged. m5 The structure represented by the formula indicates that m5 (OCF2CF2) and m5 (OCF2CF2CF2CF2) are alternately arranged.

[0031] (OR when no cycloalkylene unit is included) f2 ) m1 OR f2 ) m2 As the polyisocyanate, those having the following structure in at least a part thereof are preferred. {(OCF2) m6 (OCF2CF2) m7}, (OCF2CF2) m8 , (OCF2CF2CF2) m9 , (OCF2CF2-OCF2CF2CF2CF2) m10 , (OCF2CF2CF2CF2CF2) m11 (OCF2) m12 , (OCF2CF2CF2CF2CF2) m11 (OCF2CF2) m12 , (OCF2CF2CF2CF2CF2CF2) m11 (OCF2) m12 , (OCF2CF2CF2CF2CF2CF2) m11 (OCF2CF2) m12 , (OCF2CF2CF2CF2CF2CF2-OCF2) m13 , (OCF2CF2CF2CF2CF2-OCF2CF2) m13 , (OCF2CF2CF2CF2CF2CF2CF2-OCF2) m13 , (OCF2CF2CF2CF2CF2CF2CF2-OCF2CF2) m13 , (OCF2-OCF2CF2CF2CF2CF2) m13 , (OCF2-OCF2CF2CF2CF2CF2CF2) m13 , (OCF2CF2-OCF2CF2CF2CF2CF2) m13 , (OCF2CF2-OCF2CF2CF2CF2CF2CF2) m13 , (OCF(CF3)CF2) m14 . However, m6, m7, m8, m9, m10, m11, m12, m13, and m14 are integers equal to or greater than 1. The upper limit values ​​of m6, m7, m8, m9, m10, m11, m12, m13, and m14 are adjusted according to the upper limit values ​​of m1 and m2.

[0032] (OR when no cycloalkylene unit is included) f2 ) m1 OR f2 ) m2 As the compound 1A or 1B, the following compounds are preferred in terms of ease of production. {(OCF2) m6 (OCF2CF2) m7}OCF2, (OCF2CF2) m8 OCF2, (OCF2CF2CF2) m9 OCF2CF2, (OCF2CF2)2{(OCF2) m6 (OCF2CF2) m7}OCF2, (OCF2CF2-OCF2CF2CF2CF2) m10 OCF2CF2OCF2CF2CF2, (OCF2-OCF2CF2CF2CF2CF2) m13 OCF2OCF2CF2CF2CF2, (OCF2-OCF2CF2CF2CF2CF2CF2) m13OCF2OCF2CF2CF2CF2CF2CF2, (OCF2CF2-OCF2CF2CF2CF2CF2) m13 OCF2CF2OCF2CF2CF2CF2, (OCF2CF2-OCF2CF2CF2CF2CF2CF2) m13 OCF2CF2OCF2CF2CF2CF2CF2, (OCF(CF3)CF2) m14 OCF(CF3).

[0033] (OR when containing cycloalkylene units f2 ) m1 OR f2 ) m2 As the polyisocyanate, those having the following structure in at least a part thereof are preferred. (OCF2CF2-OCF2CF2CF2CF2) m15 -O(c-C4F6)-(OCF2CF2CF2CF2-OCF2CF2) m16 , (OCF2CF2CF2CF2-O(c-C4F6)) m17 , (OCF2CF2-OCF2CF2CF2CF2CF2CF2) m18 -O(c-C4F6)-(OCF2CF2CF2CF2CF2CF2-OCF2CF2) m19 . Here, c-C4F6 is a perfluoro-1,2-cyclobutylene group, and m15, m16, m17, m18, and m19 are integers of 1 or greater. The upper limits of m15, m16, m17, m18, and m19 are adjusted according to the upper limits of m1 and m2.

[0034] (OR when containing cycloalkylene units f2 ) m1 OR f2 ) m2 As the compound 1A or 1B, the following compounds are preferred in terms of ease of production. OCF2CF2CF2(OCF2CF2-OCF2CF2CF2CF2) m15-O(c-C4F6)-(OCF2CF2CF2CF2-OCF2CF2) m16 OCF2CF2CF2, OCF2CF2(OCF2CF2CF2CF2-O(c-C4F6)) m17 OCF2CF2CF2, O(c-C4F6)(OCF2CF2CF2CF2-O(c-C4F6)) m17 OCF2CF2CF2, OCF2CF2CF2(OCF2CF2-OCF2CF2CF2CF2CF2CF2) m15 -O(c-C4F6)-(OCF2CF2CF2CF2CF2CF2-OCF2CF2) m16 OCF2CF2CF2.

[0035] Q 1 is a (g+1)-valent linear or branched organic group, -OC(=O)-Q 1 constitutes a linking group. Q 1 When (g+1) is 3 or greater, it is preferable that the copolymer has at least one branch point (hereinafter referred to as "branch point P") selected from the group consisting of C, N, Si, a ring structure, and a (g+1)-valent organopolysiloxane residue.

[0036] As the ring structure, from the viewpoints of ease of production of Compound 1A or Compound 1B and of further improving the abrasion resistance, light resistance, and chemical resistance of the surface layer, one type selected from the group consisting of a 3- to 8-membered aliphatic ring, a 3- to 8-membered aromatic ring, a 3- to 8-membered heterocycle, and a fused ring consisting of two or more of these rings is preferred, and the ring structure shown in the following formula is particularly preferred. The ring structure may have a substituent such as a halogen atom, an alkyl group (which may contain an ethereal oxygen atom between carbon atoms), a cycloalkyl group, an alkenyl group, an allyl group, an alkoxy group, or an oxo group (=O).

[0037] [ka]

[0038] Examples of the (g+1)-valent organopolysiloxane residue include the following groups: 5 is a hydrogen atom, an alkyl group, an alkoxy group, or a phenyl group. 5 The alkyl group and alkoxy group preferably have 1 to 10 carbon atoms, and particularly preferably 1 carbon atom.

[0039] [ka]

[0040] Q 1 is -C(O)NR 6 -, -C(O)O-, -C(O)-, -O-, -NR 6 -, -S-, -OC(O)O-, -NHC(O)O-, -NHC(O)NR 6 -,-SO2NR 6 -, -Si(R 6 )2-, -OSi(R 6 )2-, -Si(CH3)2-Ph-Si(CH3)2-, and a divalent organopolysiloxane residue (hereinafter referred to as "bond B"). 6 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group, and Ph is a phenylene group. 6 The number of carbon atoms in the alkyl group is preferably 1 to 3, and particularly preferably 1 or 2, from the viewpoint of ease of production of Compound 1A or Compound 1B.

[0041] Examples of the divalent organopolysiloxane residue include groups of the following formula: 7 is a hydrogen atom, an alkyl group, an alkoxy group, or a phenyl group. 7 The alkyl group and alkoxy group preferably have 1 to 10 carbon atoms, and particularly preferably 1 carbon atom.

[0042] [ka]

[0043] As the bond B, -C(O)NR is preferred from the viewpoint of ease of producing compound 1A or compound 1B. 6 -, -C(O)-, -NR 6 At least one bond selected from the group consisting of - and -O- is preferred, and -C(O)NR is preferred in that the light resistance and chemical resistance of the surface layer are further improved. 6 - or -C(O)- is particularly preferred.

[0044] Q 1 Examples of the alkyl group include a combination of two or more divalent hydrocarbon groups and one or more branching points P, or a combination of two or more hydrocarbon groups, one or more branching points P, and one or more bonds B. Examples of the divalent hydrocarbon group include divalent aliphatic hydrocarbon groups (such as alkylene groups and cycloalkylene groups) and divalent aromatic hydrocarbon groups (such as phenylene groups). The divalent hydrocarbon group preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, and particularly preferably 1 to 4 carbon atoms.

[0045] Q 1 As the group, a group represented by any one of the following formulae (Q1) to (Q7) is preferred in terms of ease of production of compound 1.

[0046] [ka] -A 1 -C(R e2 ) 3-g3 (-Q 22 -) g3 Formula (Q2) -A 2 -N(-Q 23 -)2 equation (Q3) -A 3 -Z 1 (-Q 24 -) g4 Formula (Q4) -A 2 -Si(R e3 ) 3-g3 (-Q 25 -) g3 Formula (Q5) -A 1 -Q 26- Formula (Q6) -A 1 -CH(-Q 22 -)-Si(R e3 ) 3-g5 (-Q 25 -) g5 Formula (Q7) However, in formulas (Q1) to (Q7), A 1 , A 2 or A 3 The side connects to -OC(=O)- in formula 1, and Q 22 , Q 23 , Q 24 , Q 25 or Q 26 The side connects to the T, A 1 represents a single bond, an alkylene group, or an alkylene group having two or more carbon atoms with -C(O)NR between carbon atoms. e6 -, -C(O)-, -NR e6 - or -O-, A 2 represents an alkylene group or an alkylene group having two or more carbon atoms with -C(O)NR between carbon atoms. e6 -, -C(O)-, -NR e6 - or -O-, A 3 is A 3 Z binds to 1 If the atom in is a carbon atom, then A 1 and A 3 Z binds to 1 If the atom in is a nitrogen atom, A 2 and Q 11 represents a single bond, -O-, an alkylene group, or -C(O)NR between carbon atoms of an alkylene group having two or more carbon atoms. e6 -, -C(O)-, -NR e6 - or -O-, Q 22 is an alkylene group, an alkylene group with two or more carbon atoms that has -C(O)NR between carbon atoms. e6 -, -C(O)-, -NR e6 a group having - or -O-, and -C(O)NR at the end of the alkylene group not connected to T e6-, -C(O)-, -NR e6 A group having - or -O-, or an alkylene group having 2 or more carbon atoms having -C(O)NR between carbon atoms. e6 -, -C(O)-, -NR e6 - or -O- and -C(O)NR at the end not connected to T e6 -, -C(O)-, -NR e6 - or -O-, and Q 1 Q 22 If there are two or more, there are two or more Q 22 may be the same or different, Q 23 represents an alkylene group or an alkylene group having two or more carbon atoms with -C(O)NR between carbon atoms. e6 -, -C(O)-, -NR e6 - or -O-, and two Q 23 may be the same or different, Q 24 Q 24 Z binds to 1 If the atom in is a carbon atom, then Q 22 and Q 24 Z binds to 1 If the atom in is a nitrogen atom, Q 23 and Q 1 Q 24 If there are two or more, there are two or more Q 24 may be the same or different, Q 25 represents an alkylene group or an alkylene group having two or more carbon atoms with -C(O)NR between carbon atoms. e6 -, -C(O)-, -NR e6 - or -O-, and Q 1 Q 25 If there are two or more, there are two or more Q 25 may be the same or different, Q 26 represents an alkylene group or an alkylene group having two or more carbon atoms with -C(O)NR between carbon atoms. e6 -, -C(O)-, -NR e6 - or -O-, Z 1is A 3 has a carbon atom or nitrogen atom to which Q is directly bonded, 24 has a carbon atom or nitrogen atom directly bonded to it (g 4 a group having a +1)valent ring structure, R e1 is a hydrogen atom or an alkyl group, and Q 1 R e1 If there are two or more, there are two or more R e1 may be the same or different, R e2 is a hydrogen atom, a hydroxyl group, an alkyl group, or an acyloxy group, R e3 is an alkyl group, R e6 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group, g1 is an integer of 0 to 3, g2 is an integer of 0 to 3, and g1+g2 is an integer of 1 to 6; g3 is an integer from 1 to 3, g4 is an integer equal to or greater than 1, g5 is an integer from 0 to 3. Note that g1+g2=g, g3=g, g4=g, and g5+1=g.

[0047] Q 11 , Q 22 , Q 23 , Q 24 , Q 25 or Q 26 The number of carbon atoms in the alkylene group is preferably 1 to 10, more preferably 1 to 6, and particularly preferably 1 to 4, from the viewpoints of ease of production of Compound 1A or Compound 1B and of further improving the abrasion resistance, light resistance, and chemical resistance of the surface layer. However, when a specific bond is present between carbon atoms, the lower limit of the number of carbon atoms in the alkylene group is 2.

[0048] Examples of the ring structure in Z include the ring structures described above, and the preferred embodiments are also the same. 24is directly bonded, for example, an alkylene group is connected to the ring structure, and Q 24 are never connected.

[0049] R e1 , R e2 or R e3 The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 or 2, from the viewpoint of ease of production of Compound 1A or Compound 1B. R e2 The number of carbon atoms in the alkyl group portion of the acyloxy group is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 or 2, in terms of ease of production of compound 1. g4 is preferably 2 to 6, more preferably 2 to 4, and particularly preferably 2 or 3, in terms of ease of production of compound 1A or compound 1B and further improved abrasion resistance and fingerprint stain removability of the surface layer.

[0050] Q 1 Other examples of the group include groups represented by any of the following formulae (Q11) to (Q17).

[0051] [ka] -A 1 -C(R e2 ) 3-g3 (-Q 22 -G) g3 Formula (Q12) -A 2 -N(-Q 23 -G)2 formula (Q13) -A 3 -Z 1 (-Q 24 -G) g4 Formula (Q14) -A 2 -Si(R e3 ) 3-g3 (-Q 25 -G) g3 Formula (Q15) -A 1 -Q 26 -G formula (Q16) -A 1-CH(-Q 22 -)-Si(R e3 ) 3-g5 (-Q 25 -G) g5 Formula (Q17)

[0052] However, in equations (Q11) to (Q17), A 1 , A 2 or A 3 The side connects to -OC(=O)- in formula 1, and Q 22 , Q 23 , Q 24 , Q 25 or Q 26 The side connects to T. G is the group g3 shown below, and Q 1 The two or more G's may be the same or different. The symbols other than G are the same as those in formulae (Q1) to (Q7). -Si(R 8 ) 3-k (-Q 3 -) k formula g3 However, in equation g3, the Si side is Q 22 , Q 23 , Q 24 , Q 25 or Q 26 Connect to Q 3 The side connects to the T. 8 is an alkyl group. 3 is an alkylene group, an alkylene group with two or more carbon atoms that has -C(O)NR between carbon atoms. 6 -, -C(O)-, -NR 6 - or a group having -O-, or -(OSi(R 9 )2) p -O- and 2 or more Q 3 may be the same or different. k is 2 or 3. R 6 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. 9 is an alkyl group, a phenyl group, or an alkoxy group, and two R 9 may be the same or different. p is an integer of 0 to 5, and when p is 2 or more, 2 or more (OSi(R 9)2) may be the same or different.

[0053] Q 3 The number of carbon atoms in the alkylene group is preferably 1 to 10, more preferably 1 to 6, and particularly preferably 1 to 4, from the viewpoints of ease of production of Compound 1A or Compound 1B and of further improving the abrasion resistance, light resistance, and chemical resistance of the surface layer. However, when a specific bond is present between carbon atoms, the lower limit of the number of carbon atoms in the alkylene group is 2. R 8 The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 or 2, from the viewpoint of ease of production of Compound 1A or Compound 1B. R 9 The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 or 2, from the viewpoint of ease of production of Compound 1A or Compound 1B. R 9 The number of carbon atoms in the alkoxy group is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 or 2, in terms of excellent storage stability of Compound 1A or Compound 1B. p is preferably 0 or 1.

[0054] T is -Si(R) 3-a (L) a and is a reactive silyl group. The number of carbon atoms in the alkyl group of R is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 or 2, from the viewpoint of ease of production of compound 1A or compound 1B.

[0055] L is a hydrolyzable group or a hydroxyl group. The hydrolyzable group L is a group that becomes a hydroxyl group upon hydrolysis. That is, a hydrolyzable silyl group represented by Si-L becomes a silanol group represented by Si-OH upon hydrolysis. The silanol groups further react with each other to form Si-O-Si bonds. Furthermore, the silanol groups can undergo a dehydration condensation reaction with hydroxyl groups (substrate-OH) on the surface of the substrate to form chemical bonds (substrate-O-Si). Specific examples of L include an alkoxy group, an aryloxy group, a halogen atom, an acyl group, an acyloxy group, and an isocyanate group (-NCO). The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms. The aryloxy group is preferably an aryloxy group having 3 to 10 carbon atoms. The halogen atom is preferably a chlorine atom. The acyl group is preferably an acyl group having 1 to 6 carbon atoms. The acyloxy group is preferably an acyloxy group having 1 to 6 carbon atoms. L is preferably an alkoxy group having 1 to 4 carbon atoms or a halogen atom. It is particularly preferable that a is 3, since this will result in stronger adhesion between the surface layer and the substrate. The multiple T's in Compound 1A or Compound 1B may be the same or different, and are preferably the same group from the viewpoint of ease of production of Compound 1A or Compound 1B.

[0056] g represents the number of reactive silyl groups. g In terms of ease of production of compound 1 and further superior abrasion resistance and fingerprint stain removability of the surface layer, 1 to 6 are preferred, 1 to 5 are more preferred, 1 to 4 are further preferred, and 2 to 4 are particularly preferred.

[0057] Specific examples of the present compound include the compound of the following formula: The compound of the following formula is easy to produce industrially, easy to handle, and has the properties of water and oil repellency, abrasion resistance, fingerprint stain removal, lubrication, and the like of a surface layer. sex, The compound R in the following formula is preferred because it has better light resistance and chemical resistance, and especially better chemical resistance. f is R in the above formula 1 f In the compounds of the following formulae, m21 to m39 and n21 to n39 represent repeating units, and mx+nx (x is 21 to 39) is 1 to 500.

[0058] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0059] (Method for producing the present compound) An example of a method for producing the present compound will be described below. Although the production method is not limited to the following method, the present compound can be obtained in high yield by the following method.

[0060] The present compound can be produced, for example, by a method of subjecting the following compound 2 to a hydrosilylation reaction with the following compound 3a or compound 3b. R f [-R 1 -OC(=O)-Q 10 {-CH=CH2} g ] j formula 2 However, in Equation 2, Q 10 is a (g+1)-valent organic group, and Q 10 The symbols other than are the same as those in Equation 1. Q 10 {-CH=CH2} g is the Q in compound 1 after hydrosilylation 1 Q 10 As for Q 1 The same groups as those mentioned above can be mentioned, and the preferred forms are also the same.

[0061] HSi® 3-a (L) a formula 3a HSi(R 8 ) 3-k [-(OSi(R 9 )2) p -O-Si(R) 3-a (L) a ] k formula 3b However, the symbols in Formula 3a and Formula 3b are the same as the symbols in Formula 1A, Formula 1B, and Formula g3. Compound 3b can be produced, for example, by the method described in the specification of Japanese Patent Application No. 2018-085493.

[0062] The compound 2 can be produced, for example, by reacting the following compound 4a with the following compound 4b. R f [-R 1 -OH] j formula 4a XC(=O)-Q 10 {-CH=CH2} g formula 4b However, among the symbols in formula 4a and formula 4b, X is a halogen atom, and the symbols other than X are the same as the symbols in formula 1 and formula 2. Examples of X include a fluorine atom, a chlorine atom, and a bromine atom, and a chlorine atom is preferable. Compounds 4a and 4b may be synthesized or commercially available products may be used.

[0063] [Fluorine-containing compound-containing composition] The fluorine-containing compound-containing composition of the present invention (hereinafter also referred to as the present composition) is a composition containing the fluorine-containing compound of the present invention, a fluorine-containing compound other than the present compound, and at least one of the impurities described below. Examples of impurities include compounds that are unavoidable in the production of the present compound and other fluorine-containing compounds. Note that the present composition does not contain a liquid medium, which will be described later.

[0064] Examples of other fluorine-containing compounds include fluorine-containing compounds produced as by-products in the production process of the present compound (hereinafter also referred to as by-product fluorine-containing compounds), and known fluorine-containing compounds used for the same purposes as the present compound. As the other fluorine-containing compound, a compound which is unlikely to deteriorate the properties of the present compound is preferred. In order to fully exhibit the properties of the present compound, the content of the other fluorine-containing compounds is preferably less than 50 mass %, more preferably less than 30 mass %, and even more preferably less than 10 mass % of the total amount of the present composition.

[0065] Examples of by-product fluorine-containing compounds include unreacted fluorine-containing compounds during the synthesis of the present compound. When the present composition contains a by-product fluorine-containing compound, the purification step for removing the by-product fluorine-containing compound or reducing the amount of the by-product fluorine-containing compound can be simplified.

[0066] Known fluorine-containing compounds include, for example, those described in the following documents: perfluoropolyether-modified aminosilanes described in Japanese Patent Application Laid-Open No. 11-029585; Silicon-containing organic fluorine-containing polymers described in Japanese Patent No. 2874715; Organosilicon compounds described in Japanese Patent Application Laid-Open No. 2000-144097; perfluoropolyether-modified aminosilanes described in Japanese Patent Application Laid-Open No. 2000-327772; Fluorinated siloxanes described in Japanese Patent Publication No. 2002-506887; Organosilicon compounds described in Japanese Patent Application Laid-Open No. 2008-534696; Fluorinated modified hydrogen-containing polymers described in Japanese Patent No. 4138936; Compounds described in U.S. Patent Application Publication No. 2010 / 0129672, WO 2014 / 126064, and JP 2014-070163 A; Organosilicon compounds described in WO 2011 / 060047 and WO 2011 / 059430; fluorine-containing organosilane compounds described in WO 2012 / 064649; Fluorooxyalkylene group-containing polymers described in Japanese Patent Application Laid-Open No. 2012-72272; fluorine-containing ether compounds described in WO 2013 / 042732, WO 2013 / 121984, WO 2013 / 121985, WO 2013 / 121986, WO 2014 / 163004, JP 2014-080473 A, WO 2015 / 087902, WO 2017 / 038830, WO 2017 / 038832, and WO 2017 / 187775; perfluoro(poly)ether-containing silane compounds described in JP 2014-218639 A, WO 2017 / 022437 A, WO 2018 / 079743 A, and WO 2018 / 143433 A; Fluoropolyether group-containing polymer-modified silanes described in Japanese Patent Application Laid-Open No. 2015-199906, Japanese Patent Application Laid-Open No. 2016-204656, Japanese Patent Application Laid-Open No. 2016-210854, and Japanese Patent Application Laid-Open No. 2016-222859 International Publication No. 2018 / 216630, International Publication No. 2019 / 039226, International Publication No. 2019 / 039341, International Publication No. 2019 / 039186 ,day Fluorine-containing ether compounds described in JP 2019-44158 A, WO 2019 / 044479 A, ​​and WO 2019 / 163282 A. Commercially available fluorine-containing compounds include the KY-100 series (KY-178, KY-185, KY-195, etc.) manufactured by Shin-Etsu Chemical Co., Ltd., Afluid (registered trademark) S550 manufactured by AGC Corporation, and OPTOOL (registered trademark) DSX, OPTOOL (registered trademark) AES, OPTOOL (registered trademark) UF503, and OPTOOL (registered trademark) UD509 manufactured by Daikin Industries, Ltd.

[0067] The proportion of the present compound in the present composition is less than 100% by mass, preferably 60% by mass or more, more preferably 70% by mass or more, and even more preferably 80% by mass or more. When the present composition contains other fluorine-containing compounds, the proportion of the other fluorine-containing compounds relative to the total of the present compound and the other fluorine-containing compounds in the present composition is preferably 40 mass% or less, more preferably 30 mass% or less, and even more preferably 20 mass% or less. The total proportion of the present compound and other fluorine-containing compounds in the present composition is preferably 80% by mass or more, more preferably 85% by mass or more. When the content of this compound and other fluorine-containing compounds is within the above range, the surface layer has excellent water and oil repellency, abrasion resistance, fingerprint stain removability, lubricity, and appearance.

[0068] [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 40% by mass, more preferably from 0.01 to 20% by mass, and more preferably from 0.1 to 10% by mass.

[0069] 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.

[0070] 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 13 H (AGC Corporation, Asahiklin (registered trademark) AC-2000), C6F 13 Examples include C2H5 (ASAHIKLIN (registered trademark) AC-6000, manufactured by AGC Corporation) and C2F5CHFCHFCF3 (VERTREL (registered trademark) XF, manufactured by Chemours Corporation). 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 AGC, 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. The non-fluorine-based organic solvent is preferably a compound consisting only of hydrogen atoms and carbon atoms, or a compound 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 75 to 99.999 mass %, more preferably 85 to 99.99 mass %, and particularly preferably 90 to 99.9 mass % of the liquid medium.

[0071] The present coating liquid may contain, in addition to the present compound or composition and the liquid medium, other components as long as the effects of the present invention are not impaired. Examples of other components include known additives such as acid catalysts and basic catalysts that promote the hydrolysis and condensation reaction of the hydrolyzable silyl groups. The content of other components in the present coating liquid is preferably 10% by mass or less, and more preferably 1% by mass or less.

[0072] The total concentration of the present compound and other components or the total concentration of the present composition and other components in the present coating liquid (hereinafter also referred to as solids concentration) is preferably 0.001 to 40 mass%, preferably 0.01 to 20 mass%, more preferably 0.01 to 10 mass%, and more preferably 0.01 to 1 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.

[0073] [Goods] FIG. 1 is a schematic cross-sectional view showing an example of an article of the present invention. The first article of the present invention is an article 20 having a substrate 12, an underlayer 14, and a surface layer 22 in this order, The underlayer contains a silicon-containing oxide, and the surface layer contains a condensate of the present compound.

[0074] The material and shape of the substrate in the first article may be appropriately selected depending on the intended use of the article. Examples of the substrate material include glass, resin, sapphire, metal, ceramic, stone, and composite materials thereof. Glass may be chemically strengthened. Substrates that require water and oil repellency in particular include substrates for touch panels, display substrates, and substrates that constitute the housings of electronic devices. Touch panel substrates and display substrates are translucent. "Translucent" means that the normal incidence visible light transmittance in accordance with JIS R3106:1998 (ISO 9050:1990) is 25% or more. Glass or transparent resin is preferred as the material for the touch panel substrate.

[0075] The substrate may be one that has been subjected to a surface treatment such as corona discharge treatment, plasma treatment, or plasma graft polymerization treatment on the surface on which the undercoat layer is to be formed. The surface that has been subjected to the surface treatment further improves the adhesion between the substrate and the undercoat layer, and as a result, the abrasion resistance of the surface layer is further improved. As the surface treatment, corona discharge treatment or plasma treatment is preferred in terms of further improving the abrasion resistance of the surface layer.

[0076] The underlayer is a layer containing at least an oxide containing silicon, and may further contain other elements. When the underlayer contains silicon oxide, the partial structure (2) of the present compound undergoes dehydration condensation, forming Si-O-Si bonds between the underlayer and the underlayer, resulting in the formation of a surface layer with excellent wear resistance.

[0077] The content of silicon oxide in the underlayer may be 65% by mass or more, preferably 80% by mass or more, more preferably 85% by mass or more, and even more preferably 90% by mass or more. When the content of silicon oxide is equal to or more than the lower limit of the above range, Si-O-Si bonds are sufficiently formed in the underlayer, and the mechanical properties of the underlayer are sufficiently ensured. The content of silicon oxide is determined by the amount of other elements. Including It is the remainder obtained by subtracting the total amount of the contained metals (or the amount converted to oxide in the case of oxides) from the mass of the underlayer.

[0078] From the viewpoint of durability of the surface layer, it is preferable that the oxide in the underlayer further contains one or more elements selected from alkali metal elements, alkaline earth metal elements, platinum group elements, boron, aluminum, phosphorus, titanium, zirconium, iron, nickel, chromium, molybdenum, and tungsten, which strengthens the bond between the underlayer and the present compound and improves wear resistance.

[0079] When the underlayer contains one or more elements selected from iron, nickel, and chromium, the total content of these elements relative to silicon oxide is preferably 10 to 1100 ppm by mass, more preferably 50 to 1100 ppm by mass, still more preferably 50 to 500 ppm by mass, and particularly preferably 50 to 250 ppm by mass. When the underlayer contains one or more elements selected from aluminum and zirconium, the total content thereof is preferably from 10 to 2500 ppm by mass, more preferably from 15 to 2000 ppm by mass, and even more preferably from 20 to 1000 ppm by mass. When the underlayer contains an alkali metal element, the total content thereof is preferably 0.05 to 15 mass %, more preferably 0.1 to 13 mass %, and even more preferably 1.0 to 10 mass %. Examples of the alkali metal element include lithium, sodium, potassium, rubidium, and cesium. When the underlayer contains a platinum group element, the total content thereof is preferably 0.02 mass ppm to 800 mass ppm, more preferably 0.04 mass ppm to 600 mass ppm, and even more preferably 0.7 mass ppm to 200 mass ppm. Examples of the platinum group element include platinum, rhodium, ruthenium, palladium, osmium, and iridium. When the underlayer contains one or more elements selected from boron and phosphorus, the total content thereof is preferably 0.003 to 9, more preferably 0.003 to 2, and even more preferably 0.003 to 0.5, in terms of the ratio of the molar concentration of the sum of boron and phosphorus to the molar concentration of silicon, from the viewpoint of the wear resistance of the surface layer. When the underlayer contains alkaline earth metal elements, the total content thereof, expressed as the ratio of the molar concentration of the total alkaline earth metal elements to the molar concentration of silicon, is preferably 0.005 to 5, more preferably 0.005 to 2, and even more preferably 0.007 to 2, from the viewpoint of the abrasion resistance of the surface layer. Examples of alkaline earth metal elements include lithium, sodium, potassium, rubidium, and cesium.

[0080] From the viewpoint of improving the adhesiveness of the present compound and improving the water / oil repellency and abrasion resistance of the article, the underlayer is preferably a silicon oxide layer containing alkali metal atoms. In particular, in the silicon oxide layer, the average concentration of alkali metal atoms in a region 0.1 to 0.3 nm deep from the surface in contact with the surface layer is 2.0 × 10 19 atoms / cm 3 On the other hand, in order to ensure sufficient mechanical properties of the silicon oxide layer, the average concentration of the alkali metal atoms is preferably 4.0×10 or more. 22 atoms / cm 3 It is preferable that:

[0081] The thickness of the underlayer is preferably 1 to 200 nm, and particularly preferably 2 to 20 nm. If the thickness of the underlayer is equal to or greater than the lower limit of the above range, the underlayer is likely to have a sufficient effect of improving adhesion. If the thickness of the underlayer is equal to or less than the upper limit of the above range, the abrasion resistance of the underlayer itself is increased. Methods for measuring the thickness of the underlayer include a method of observing the cross section of the underlayer using an electron microscope (SEM, TEM, etc.), and a method using an optical interference film thickness meter, a spectroscopic ellipsometer, a step gauge, etc.

[0082] The underlayer may be formed, for example, by depositing a deposition material having a desired composition for the underlayer on the surface of the substrate. An example of the vapor deposition method is vacuum deposition, in which a deposition material is evaporated in a vacuum chamber and attached to the surface of a substrate. The temperature during vapor deposition (for example, the temperature of the boat where the vapor deposition material is placed when a vacuum vapor deposition device is used) is preferably 100 to 3000°C, particularly preferably 500 to 3000°C. The pressure during vapor deposition (for example, when using a vacuum vapor deposition apparatus, the absolute pressure in a tank in which the vapor deposition material is placed is preferably 1 Pa or less, and particularly preferably 0.1 Pa or less. When the underlayer is formed using a deposition material, one deposition material may be used, or two or more deposition materials containing different elements may be used. Examples of methods for evaporating the deposition material include a resistance heating method in which the deposition material is melted and evaporated on a resistance heating boat made of a high-melting-point metal, and an electron gun method in which the deposition material is irradiated with an electron beam to directly heat the deposition material, melting and evaporating the surface. The electron gun method is preferred as a method for evaporating the deposition material because it can evaporate high-melting-point substances due to its ability to heat locally, and because areas not irradiated by the electron beam are at low temperatures, there is no risk of reaction with the container or contamination with impurities. The deposition material used in the electron gun method is preferably a molten granular or sintered material because it is less likely to scatter even when an air current is generated.

[0083] The surface layer on the underlayer contains a condensate of the present compound. Condensates of the present compound include those in which hydrolyzable silyl groups in the present compound undergo hydrolysis to form silanol groups (Si-OH), which then undergo intermolecular condensation to form Si-O-Si bonds, and those in which silanol groups in the present compound undergo condensation with silanol groups or Si-OM groups (wherein M is an alkali metal element) on the surface of the underlayer to form Si-O-Si bonds. The surface layer may also contain a condensate of a fluorine-containing compound other than the present compound. That is, the surface layer contains a fluorine-containing compound having reactive silyl groups in a state in which some or all of the reactive silyl groups of the fluorine-containing compound have undergone condensation reaction.

[0084] The thickness of the surface layer is preferably 1 to 100 nm, 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 layer can be sufficiently 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 is the thickness obtained using an X-ray diffractometer for thin film analysis. The thickness of the surface layer can be calculated from the oscillation period of the interference pattern obtained by X-ray reflectivity analysis using an X-ray diffractometer for thin film analysis.

[0085] A second article of the present invention is an article 20 having a substrate 12 and a surface layer 22 in this order, the substrate contains an oxide containing silicon, The surface layer contains a condensate of the present compound.

[0086] In the second article, the substrate has the same composition as the undercoat layer in the first article, and therefore the surface layer has excellent abrasion resistance even when the surface layer is formed directly on the substrate. The material of the substrate in the second article may be any material having the composition of the underlayer, such as a glass substrate. Details of the material of the substrate are the same as those of the underlayer, and therefore a detailed description thereof will be omitted. Furthermore, the configuration of the surface layer is also the same as that of the first article, and therefore a detailed description thereof will be omitted.

[0087] [Production method] The method for producing an article according to the present invention is a method for forming a surface layer by a dry coating method or a wet coating method using the fluorine-containing compound, the fluorine-containing compound-containing composition, or the coating liquid.

[0088] 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. For vacuum deposition, a pellet-shaped material in which the present compound is supported on a porous metal body made of a metal material such as iron or steel may be used. The pellet-shaped material supporting the present compound can be produced by impregnating a porous metal body with a solution of the present compound and drying it to remove the liquid medium. The solution of the present compound can be the present coating liquid.

[0089] The coating liquid can be suitably used for wet coating methods such as 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.

[0090] 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 the hydrolyzable groups, the reaction between hydroxyl groups on the surface of the substrate and silanol groups, and the formation of siloxane bonds through the condensation reaction of the 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]

[0091] The present invention will be described in more detail below using examples, but the present invention is not limited to these examples. In the following, "%" means "% by mass" unless otherwise specified. Examples 1 to 18 and Examples 20 and 21 are examples, and Example 19 is a comparative example. In the following, C6F 13 H is represented as AC2000, CF3CF2CF2CF2CF2CF2CH2CH3 as AC6000, ClCF2CFClCF2OCF2CF2Cl as CFE-419, and CF3CF2CHCl2 as AK-225.

[0092] [Example 1] (Example 1-1) Compound (A-1) was obtained according to the method described in Example 2-3 of the Examples of WO 2013 / 121984. CF3(OCF2CF2OCF2CF2CF2CF2) x1 OCF2CF2OCF2CF2CF2-C(=O)OCH3 formula (A-1) However, the average value of x1 is 13.

[0093] (Example 1-2) 2.4 g of sodium borohydride powder was placed in a 300 cc three-necked round-bottom flask, and 15 g of AC2000 was added. The mixture was cooled in an ice bath while stirring, and under a nitrogen atmosphere, a solution containing 30 g of compound (A-1), 4 g of methanol, and 60 g of AC2000 was slowly added dropwise from the dropping funnel so that the internal temperature did not exceed 10°C. After the entire amount was added, an additional 4 g of methanol was added dropwise. The mixture was then stirred at 10°C. The mixture was again cooled in an ice bath, and an aqueous hydrochloric acid solution was added dropwise. After the reaction was completed, the mixture was washed successively with hydrochloric acid and water, and the organic phase was recovered. The recovered organic phase was concentrated and evaporated under reduced pressure to obtain 29 g of compound (A-2). CF3(OCF2CF2OCF2CF2CF2CF2) m1 OCF2CF2OCF2CF2CF2-CH2-OH Formula (A-2)

[0094] (Example 1-3) 0.67 g of HO(C=O)C(CH2CH=CH2)3, 33 mL of dichloromethane, and 0.67 mL of oxalyl chloride were added to a 200 cc recovery flask and stirred under ice cooling, followed by the addition of 0.0393 g of DMF (N,N-dimethylformamide). After stirring at room temperature, the mixture was concentrated to obtain 0.6 g of Cl(C=O)C(CH2CH=CH2)3. Separately, 7 g of compound (A-2), 7 g of AC6000, 0.4 g of triethylamine, 0.2 g of N,N-dimethyl-4-aminopyridine were added to a 50 cc recovery flask, and 0.6 g of the above Cl(C=O)C(CHCH=CH) was added, followed by stirring at 30° C. The resulting reaction solution was purified by silica gel chromatography to obtain 5.8 g of compound (A-3). CF3O(CF2CF2OCF2CF2CF2CF2O) x1 CF2CF2OCF2CF2CF2-CH2O(C=O)C(CH2CH=CH2)3 formula (A-3)

[0095] (Example 1-4) A 50 cc recovery flask purged with nitrogen was charged with 1.0 g of compound (A-3), 0.003 g of a xylene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass), 0.0009 g of aniline, and 1.0 g of AC6000, followed by 0.11 g of trimethoxysilane and stirring for 4 hours at 40° C. An additional 0.003 g of a xylene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass), aniline, and AC6000 were then added and stirred, after which the solvent was distilled off to obtain 1.1 g of compound (1-A) (yield 95%). CF3O(CF2CF2OCF2CF2CF2CF2O) x1 CF2CF2OCF2CF2CF2-CH2O(C=O)C[CH2CH2CH2Si(OCH3)3]3 formula (1-A)

[0096] [Example 2] (Example 2-1) The following compound (1-B) was obtained in the same manner as in Example 1, except that in Example 1-3, HO(C=O)C(CH2CH=CH2)3 was changed to HO(C=O)CH(CH2CH=CH2)2. CF3(OCF2CF2OCF2CF2CF2CF2) x2 OCF2CF2OCF2CF2CF2-CH2O(C=O)CH[CH2CH2CH2Si(OCH3)3]2 formula (1-B) However, the average value of x2 is 13.

[0097] [Example 3] (Example 3-1) Compound (C-1) was obtained by the method described in Examples 1-1 to 1-4 of the Examples of WO 2017 / 038830. CF3CF2CF2(OCF2CF2)(OCF2CF2)[(OCF2) x3 (OCF2CF2) y3 ]OCF2C(=O)OCH3 Formula (C-1) However, the average value of x3 is 21 and the average value of y3 is 20.

[0098] (Example 3-2) The following compound (1-C) was obtained in the same manner as in Example 1, except that in Example 1-2, compound (A-1) was changed to compound (C-1). CF3CF2CF2(OCF2CF2)(OCF2CF2)[(OCF2) x3 (OCF2CF2) y3 ]OCF2CH2O(C=O)C[CH2CH2CH2Si(OCH3)3]3 formula (1-C) However, the average value of x3 is 21 and the average value of y3 is 20.

[0099] [Example 4] (Example 4-1) The following compound (1-D) was obtained in the same manner as in Example 3, except that in Example 1-3 cited in Example 3, HO(C=O)C(CHCH=CH) was changed to HO(C=O)CH(CHCH=CH). CF3CF2CF2(OCF2CF2)(OCF2CF2)[(OCF2) x4 (OCF2CF2) y4 ]OCF2CH2O(C=O)CH[CH2CH2CH2Si(OCH3)3]2 formula (1-D) However, the average value of x4 is 21 and the average value of y4 is 20.

[0100] [Example 5] (Example 5-1) Compound (E-1) was obtained according to the method described in Example 1-1 of the Examples of WO 2013 / 121984. CF2=CF-O-CF2CF2CF2CH2-OH Formula (E-1)

[0101] (Example 5-2) In a 200 mL recovery flask, 16.2 g of HO-CH2CF2CF2CH2-OH and 13.8 g of potassium carbonate were placed and stirred at 120 ° C., and 278 g of the compound (E-1) was added and stirred at 120 ° C. The mixture was returned to 25 ° C., and 50 g each of AC2000 and hydrochloric acid were added, followed by separation and concentration of the organic phase. The resulting crude reaction liquid was purified by column chromatography to obtain 117.7 g of compound (E-2) (yield 40%).

[0102] [ka]

[0103] (Example 5-3) 20 g of compound (E-2), 2.4 g of sodium fluoride powder, 20 g of AC-2000, and 18.8 g of CFCFCFOCF(CF)COF were added to a 50 mL recovery flask equipped with a reflux condenser. The mixture was stirred at 50°C under a nitrogen atmosphere. After cooling to room temperature, the sodium fluoride powder was removed using a pressure filter, and then excess CFCFCFOCF(CF)COF and AC-2000 were distilled off under reduced pressure to obtain 24 g of compound (E-3) (yield 100%).

[0104] [ka]

[0105] (Example 5-4) 250 mL of CFE-419 was placed in a 500 mL nickel reactor and nitrogen gas was bubbled through. After the oxygen gas concentration had sufficiently decreased, 20% by volume fluorine gas diluted with nitrogen gas was bubbled through for 1 hour. A CFE-419 solution of compound (E-3) (concentration: 10% by mass, compound (E-3): 24 g) was added. The ratio of the fluorine gas introduction rate (mol / hour) to the hydrogen atom introduction rate (mol / hour) in compound (E-3) was controlled to 2:1. After the addition of compound (E-3) was completed, a CFE-419 solution of benzene (concentration: 0.1% by mass, benzene: 0.1 g) was intermittently added. After the addition of benzene was completed, fluorine gas was bubbled through, and finally, the reactor was thoroughly purged with nitrogen gas. The solvent was distilled off, yielding 25.3 g of compound (E-4) (yield: 90%). CF3CF2CF2-OCF(CF3)-C(=O)-O-CF2CF2CF2CF2-(OCF2CF2-OCF2CF2CF2CF2) x5 -OCF2CF2-OCF2CF2CF2CF2-OC(=O)-CF(CF3)O-CF2CF2CF3 formula (E-4)

[0106] (Example 5-5) 25.3 g of compound (E-4), 2.2 g of sodium fluoride, and 25 mL of AC-2000 were placed in a 50 mL recovery flask and stirred in an ice bath. 1.7 g of methanol was added and stirred at 25°C. After filtration, the filtrate was purified by column chromatography to obtain 15 g of compound (E-5) (yield 80%). CH3-OC(=O)-CF2CF2CF2-(OCF2CF2-OCF2CF2CF2CF2) x5 -OCF2CF2-OCF2CF2CF2-C(=O)-O-CH3 formula (E-5) However, the average value of x5 is 13.

[0107] (Example 5-6) A 50 cc three-necked round-bottom flask was charged with 1.6 g of sodium borohydride powder and 5 g of AC2000. The mixture was cooled in an ice bath while stirring, and under a nitrogen atmosphere, a solution containing 10 g of compound (E-5), 1.3 g of methanol, and 20 g of AC2000 was slowly added dropwise from the dropping funnel so that the internal temperature did not exceed 10°C. After the entire amount was added, an additional 1.3 g of methanol was added dropwise. The mixture was then stirred at 10°C. The mixture was again cooled in an ice bath, and aqueous hydrochloric acid was added dropwise. After the reaction was completed, the mixture was washed successively with hydrochloric acid and water, and the organic phase was recovered. The recovered organic phase was concentrated and evaporated under reduced pressure to obtain 9.7 g of compound (E-7). HOCH2CF2CF2CF2O-(CF2CF2O-CF2CF2CF2CF2O) x5 -CF2CF2O-CF2CF2CF2CH2OH Formula (E-6) However, the average value of x5 is 13.

[0108] (Example 5-7) 0.67 g of HO(C=O)C(CH2CH=CH2)3, 33 mL of dichloromethane, and 0.67 mL of oxalyl chloride were added to a 200 cc recovery flask and stirred under ice cooling, followed by the addition of 0.0393 g of DMF (N,N-dimethylformamide). After stirring at room temperature, the mixture was concentrated to obtain 0.6 g of Cl(C=O)C(CH2CH=CH2)3. Separately, 3.5 g of compound (E-6), 3.5 g of AC6000, 0.4 g of triethylamine, and 0.2 g of N,N-dimethyl-4-aminopyridine were added to a 50 cc recovery flask, and 0.6 g of the above Cl(C=O)C(CHCH=CH) was added and stirred. The resulting reaction solution was purified by silica gel chromatography to obtain 2.9 g of the following compound (E-7). (CH2=CHCH2)3C(C=O)OCH2CF2CF2CF2O-(CF2CF2O-CF2CF2CF2CF2O) x5 -CF2CF2O-CF2CF2CF2CH2O(C=O)C(CH2CH=CH2)3 formula (E-7) However, the average value of x5 is 13.

[0109] (Example 5-8) A nitrogen-purged 50 cc recovery flask was charged with 1.0 g of compound (E-7), 0.003 g of a xylene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass), 0.001 g of aniline, and 1.0 g of AC6000, followed by the addition of 0.21 g of trimethoxysilane and stirring at 40° C. The solvent was then distilled off, yielding 1.2 g of compound (1-E) (yield 100%). [(CH3O)3SiCH2CH2CH2]3C-C(=O)-O-CH2-CF2CF2CF2-(OCF2CF2-OCF2CF2CF2CF2) x5 -OCF2CF2-OCF2CF2CF2CH2-O-(C=O)-C[CH2CH2CH2Si(OCH3)3]3 compound (1-E) However, the average value of x5 is 13.

[0110] [Example 6] (Example 6-1) Compound (F-1) was obtained according to the method described in Example 1-1 of the Examples of WO 2013-121984. CF2=CF-O-CF2CF2CF2CH2-OH Formula (F-1)

[0111] (Example 6-2) 10 g of compound (F-1) was placed in a 100 mL metal reactor and stirred at 175° C. The obtained organic phase was concentrated to obtain 6 g of compound (F-2).

[0112] [ka]

[0113] (Example 6-3) 5 g of compound (F-2) and 1.2 g of potassium carbonate were placed in a 200 mL recovery flask and stirred at 120 ° C., and 25 g of compound (F-2) was added and stirred at 120 ° C. for 2 hours. The recovery flask was brought to 25 ° C., and 30 g each of AC-2000 and hydrochloric acid were added. The liquid was separated, and the organic phase was concentrated. The resulting crude reaction liquid was purified by column chromatography to obtain 21 g of compound (F-3).

[0114] [ka] However, the average value of x6+y6 is 10.

[0115] (Example 6-4) 20 g of compound (F-3), 7.1 g of sodium fluoride powder, 20 g of AC-2000, and 20 g of CFCFCFOCF(CF)COF were added to a 50 mL recovery flask. The mixture was stirred at 50°C for 24 hours under a nitrogen atmosphere. After the temperature inside the recovery flask was brought to 25°C, the sodium fluoride powder was removed by filtration. Excess CFCFCFOCF(CF)COF and AC-2000 were distilled off under reduced pressure to obtain 24 g of compound (F-4).

[0116] [ka]

[0117] (Example 6-5) A 500 mL metal reactor was charged with 250 mL of CFE-419, and nitrogen gas was bubbled through. Then, 20% by volume of fluorine gas diluted with nitrogen gas was bubbled through. A CFE-419 solution of compound (F-4) (concentration: 10%, compound (F-4): 20 g) was added over 3 hours. The ratio of the fluorine gas introduction rate (mol / h) to the hydrogen atom introduction rate (mol / h) in compound 4-2 was controlled to 2:1. After the addition of compound (F-4) was completed, a CFE-419 solution of benzene (concentration: 0.1%, benzene: 0.1 g) was intermittently added. After the addition of benzene was completed, fluorine gas was bubbled through, and finally, the reactor was thoroughly purged with nitrogen gas. The solvent was distilled off, yielding 21 g of compound (F-5).

[0118] [ka]

[0119] (Example 6-6) 20 g of compound (F-5), 1.8 g of sodium fluoride, and 20 mL of AC-2000 were placed in a 50 mL recovery flask and stirred in an ice bath. 1.4 g of methanol was added and stirred at 25°C for 1 hour. After filtration, the filtrate was purified by column chromatography. 14 g of compound (F-6) was obtained.

[0120] [ka]

[0121] (Example 6-7) A 50cc three-necked round-bottom flask was charged with 1.6g of sodium borohydride powder and 5g of AC2000. The mixture was cooled in an ice bath while stirring, and under a nitrogen atmosphere, a solution containing 10g of compound (F-6), 1.3g of methanol, and 20g of AC2000 was slowly added dropwise from the dropping funnel so that the internal temperature did not exceed 10°C. After the entire amount was added, an additional 1.3g of methanol was added dropwise. The mixture was then stirred at 10°C. The mixture was again cooled in an ice bath, and aqueous hydrochloric acid was added dropwise. After the reaction was complete, the mixture was washed sequentially with hydrochloric acid and water, and the organic phase was recovered. The recovered organic phase was concentrated and evaporated under reduced pressure to obtain 9.7g of compound (F-7).

[0122] [ka]

[0123] (Example 6-8) The following compound (1-F) was obtained in the same manner as in Examples 5-7 and 5-8, except that in Example 5-7, compound (E-6) was changed to compound (F-7).

[0124] [ka] However, the average value of x6+y6 is 10.

[0125] [Example 7] (Example 7-1) Compound (G-1) was synthesized by the same synthesis method as that described in Synthesis Examples 1 to 4 of Japanese Patent No. 6024816. CH3OCOCF2-(OCF2) x7 -(OCF2CF2) y7 -OCF2CO2CH3 formula (G-1) The average value of unit number x7 is 42, and the average value of unit number y7 is 10.

[0126] (Example 7-2) Compound (G-2) was synthesized according to the method described in (Example 13-1) and (Example 13-2) of WO 2018 / 216630. CF3CF2CF2-O-CHF-CF2OCH2CH2CH2CH2CH2CH2OTs Formula (G-2) (OTs represents -O-SO2-Ph-CH3, where Ph represents a phenylene group.)

[0127] (Example 7-3) A 300 mL three-neck flask was charged with 4 g of compound (G-2), 30 g of compound (G-1), and 160 g of 1,3-bis(trifluoromethyl)benzene, followed by the addition of 12 g of cesium carbonate. The mixture was stirred at 70°C under a nitrogen atmosphere. The solid was filtered and washed with water, and the organic phase was recovered. The mixture was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 12 g of compound (G-3). CF3CF2CF2-O-CHF-CF2OCH2CH2CH2CH2CH2CH2O-CH2-CF2-{(OCF2) x7 (OCF2CF2) y7}-OCF2-CH2-OH formula (G-3) The average value of unit number x7 is 42, and the average value of unit number y7 is 10.

[0128] (Example 7-4) In a 100 mL recovery flask, 12 g of compound (G-3) and 2.3 g of sodium fluoride powder were placed, and 11 g of CF3CF2CF2OCF(CF3)C(O)F was added. The mixture was stirred under a nitrogen atmosphere. After removing the sodium fluoride powder by filtration, the excess CF3CF2CF2OCF(CF3)C(O)F was distilled off under reduced pressure to obtain 12 g of compound (G-4). CF3CF2CF2-O-CHF-CF2OCH2CH2CH2CH2CH2CH2O-CH2-CF2-{(OCF2) x7 (OCF2CF2) y7}-OCF2-CH2-OC(O)CF(CF3)OCF2CF2CF3 formula (G-4) The average value of unit number x7 is 42, and the average value of unit number y7 is 10.

[0129] (Example 7-5) 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. 750 g of CFE-419 was placed in an autoclave and stirred while maintaining the temperature at 25°C. Nitrogen gas was bubbled into the autoclave at 25°C for 1 hour, followed by 20% fluorine gas bubbled in at a flow rate of 2.0 L / h for 1 hour at 25°C. While the 20% fluorine gas was bubbled in at the same flow rate, a solution of 6.0 g of compound (G-4) dissolved in 54 g of CFE-419 was injected into the autoclave over 1 hour. 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 on the autoclave was closed. After stirring, 4 mL of the benzene solution was again bubbled in while maintaining the temperature at 40°C, and the inlet was closed. The same procedure was repeated. The total amount of benzene injected was 0.17 g. Stirring was continued 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. The contents of the autoclave were concentrated using an evaporator, yielding 6.1 g of compound (G-5). CF3CF2CF2-O-CF2-CF2OCF2CF2CF2CF2CF2CF2O-CF2-CF2-{(OCF2) x7 (OCF2CF2) y7}-OCF2-CF2-OC(O)CF(CF3)OCF2CF2CF3 formula (G-5) The average value of unit number x7 is 42, and the average value of unit number y7 is 10.

[0130] (Example 7-6) 6.1 g of compound (G-5) and 10 g of AK-225 were placed in a PFA round-bottom flask. The mixture was cooled in an ice bath while stirring, and 10 g of methanol was slowly added dropwise from the dropping funnel under a nitrogen atmosphere. The mixture was stirred for 12 hours. The reaction mixture was concentrated using an evaporator to obtain 5.5 g of compound (G-6). CF3CF2CF2-O-CF2-CF2OCF2CF2CF2CF2CF2CF2O-CF2-CF2-{(OCF2) x7 (OCF2CF2) y7}-OCF2-C(O)OCH3 formula (G-6) The average value of unit number x7 is 42, and the average value of unit number y7 is 10.

[0131] (Example 7-7) The following compound (1-G) was obtained in the same manner as in Examples 1-2 to 1-4, except that in Example 1-2, compound (A-1) was replaced with compound (G-6). CF3CF2CF2-O-CF2-CF2OCF2CF2CF2CF2CF2CF2O-CF2-CF2-{(OCF2) x7 (OCF2CF2) y7}-OCF2-CH2O(C=O)C[CH2CH2CH2Si(OCH3)3]3 Formula (1-G) The average value of unit number x7 is 42, and the average value of unit number y7 is 10.

[0132] [Example 8] (Example 8-1) The following compound (1-H) was synthesized in the same manner as in Synthesis Example 7, except that in Example 1-3 cited in Example 7-7, HO(C=O)C(CHCH=CH) was changed to HO(C=O)CH(CHCH=CH). CF3CF2CF2-O-CF2-CF2OCF2CF2CF2CF2CF2CF2O-CF2-CF2-{(OCF2) x8 (OCF2CF2) y8}-OCF2-CH2O(C=O)CH[CH2CH2CH2Si(OCH3)3]2 Formula (1-H) The average value of x8 units is 42, and the average value of y8 units is 10.

[0133] [Example 9] (Example 9-1) The following compound (I-1) having a different number of repeating units from that of the compound (G-1) in Example 7-1 was synthesized. 3The following compound (I-2) was obtained in the same manner as in Examples 7-2 to 7-6, except that compound (I-1) was used instead of compound (G-1). CH3OCOCF2-(OCF2) x9 -(OCF2CF2) y9 -OCF2CO2CH3 formula (I-1) CF3CF2CF2-O-CF2-CF2OCF2CF2CF2CF2CF2CF2O-CF2-CF2-{(OCF2) x9 (OCF2CF2) y9}-OCF2-C(O)OCH3 Formula (I-2) The average value of x9 units is 26, and the average value of y9 units is 22.

[0134] (Example 9-2) Compound (1-I) was synthesized in the same manner as in Examples 1-2 to 1-4, except that Compound A-1 in Example 1-2 was changed to Compound I-2. CF3CF2CF2-O-CF2-CF2OCF2CF2CF2CF2CF2CF2O-CF2-CF2-{(OCF2) x9 (OCF2CF2) y9}-OCF2-CH2O(C=O)C[CH2CH2CH2Si(OCH3)3]3 Formula (1-I) The average value of x9 units is 26, and the average value of y9 units is 22.

[0135] [Example 10] (Example 10-1) Compound (1-J) was synthesized in the same manner as in Example 7, except that in Example 1-3 cited in Example 7-7, HO(C=O)C(CH2CH=CH2)3 was changed to HO(C=O)CH(CH2CH=CH2)2. CF3CF2CF2-O-CF2-CF2OCF2CF2CF2CF2CF2CF2O-CF2-CF2-{(OCF2) x10 (OCF2CF2) y10}-OCF2-CH2O(C=O)CH[CH2CH2CH2Si(OCH3)3]2 Formula (1-J) The average value of number of units x10 is 26, and the average value of number of units y10 is 22.

[0136] [Example 11] (Example 11-1) Compound (1-K) was synthesized in the same manner as in Examples 1-2 to 1-4, except that compound (A-1) in Example 1-2 was replaced with compound (K-1) (FLUOROLINK (registered trademark) D4000, manufactured by Solvay Solexis). HOCH2CF2-(OCF2) x11 -(OCF2CF2) y11 -OCF2CH2OH Formula (K-1) (CH2=CHCH2)3C(C=O)OCH2CF2-(OCF2) x11 -(OCF2CF2) y11 -OCF2CH2O(C=O)C[CH2CH2CH2Si(OCH3)3]3 formula (1-K) The average value of number of units x11 is 16, and the average value of number of units y11 is 18.

[0137] [Example 12] (Example 12-1) To a 50 cc recovery flask were added 7 g of compound A-2, 7 g of AC6000, 0.4 g of triethylamine, 0.2 g of N,N-dimethyl-4-aminopyridine, and 0.6 g of acryloyl chloride, and the mixture was stirred at 30°C. The obtained crude product was purified by silica gel chromatography to obtain 5.8 g of compound (L-1). CF3O(CF2CF2OCF2CF2CF2CF2O) x12 CF2CF2OCF2CF2CF2-CH2O(C=O)CCH=CH2 formula (L-1) Average value of number of units x 12: 13.

[0138] (Example 12-2) A 100 mL four-neck flask equipped with a reflux condenser, thermometer, and stirrer was charged with 20 g of compound L-1, 20 g of 1,3-bis(trifluoromethyl)benzene, 0.06 g of triacetoxymethylsilane, and 1.36 g of trichlorosilane, and the mixture was stirred at 5°C for 30 minutes under a nitrogen stream. Subsequently, 0.094 ml of a xylene solution containing 2% Pt complex of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane was added, and the mixture was heated to 60°C and stirred at this temperature for 5 hours. Volatiles were then removed under reduced pressure to obtain 19 g of compound (L-2). CF3O(CF2CF2OCF2CF2CF2CF2O) x12 CF2CF2OCF2CF2CF2-CH2O(C=O)CCH2CH2SiCl3 formula (L-2)

[0139] (Example 12-3) A 100 mL four-neck flask equipped with a reflux condenser, thermometer, and stirrer was charged with 19 g of L-2 and 20 g of 1,3-bis(trifluoromethyl)benzene and stirred for 30 minutes at 5°C under a nitrogen stream. Subsequently, 26.4 mL of a diethyl ether solution containing 0.7 mol / L of allylmagnesium bromide was added, and the mixture was warmed to room temperature and stirred at this temperature for 10 hours. The mixture was then cooled to 5°C, 5 mL of methanol was added, and the mixture was warmed to room temperature and filtered to remove insoluble matter. The volatiles were then distilled off under reduced pressure, and the non-volatiles were diluted with perfluorohexane and washed with methanol in a separatory funnel (more specifically, the fluoro-based compounds were maintained in the perfluorohexane phase (fluorous phase) and the non-fluoro-based compounds were separated and removed in the methanol phase (organic phase)). Subsequently, 20 g of compound L-3 was obtained by distilling off the volatiles under reduced pressure. CF3O(CF2CF2OCF2CF2CF2CF2O) x12 CF2CF2OCF2CF2CF2-CH2O(C=O)CCH2CH2Si(CH2CH=CH2)3 formula (L-3)

[0140] (Example 12-4) A 100 mL four-neck flask equipped with a reflux condenser, thermometer, and stirrer was charged with 15 g of compound (L-3), 15 g of 1,3-bis(trifluoromethyl)benzene, 0.05 g of triacetoxymethylsilane, and 3.15 g of trichlorosilane, and the mixture was stirred at 5°C for 30 minutes under a nitrogen stream. Subsequently, 0.141 mL of a xylene solution containing 2% Pt complex of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane was added, and the mixture was heated to 60°C and stirred at this temperature for 5 hours. Volatiles were then removed under reduced pressure to obtain 16 g of compound (L-4). CF3O(CF2CF2OCF2CF2CF2CF2O) x12 CF2CF2OCF2CF2CF2-CH2O(C=O)CCH2CH2Si(CH2CH2CH2SiCl3)3 formula (L-4)

[0141] (Example 12-5) A 100 mL four-neck flask equipped with a reflux condenser, thermometer, and stirrer was charged with 15 g of compound (L-4), 15 g of 1,3-bis(trifluoromethyl)benzene, and 0.05 g of triacetoxymethylsilane, and stirred at 50°C for 30 minutes under a nitrogen stream. Subsequently, a mixed solution of 0.5 g of methanol and 7.8 g of trimethyl orthoformate was added, and the mixture was stirred for 2 hours. Volatiles were then removed under reduced pressure to obtain 15 g of compound (1-L). CF3O(CF2CF2OCF2CF2CF2CF2O) x12 CF2CF2OCF2CF2CF2-CH2O(C=O)CCH2CH2Si[CH2CH2CH2Si(OCH3)]3 formula (1-L) Average value of number of units x 12: 13.

[0142] [Example 13] (Example 13-1) Compound (M-1) was obtained according to Example 14-5 of the Examples of WO 2017 / 038830. CF3OCF2CF2O-CF2CF2CF2CF2CF2CF2O(CF2CF2O-CF2CF2CF2CF2O) x13 CF2CF2OCF2CF2CF2C(O)OCH3 formula (M-1) Average value of number of units x 13: 9.

[0143] (Example 13-2) A 300 mL four-neck flask equipped with a Dimroth tube, dropping funnel, thermometer, and magnetic stirrer was charged with 40 g of compound M-1, 25 g of a diethyl ether solution of allylmagnesium bromide (bromo group concentration: 0.05 mol / 100 g), 40 g of 1,3-bistrifluoromethylbenzene, and 13 g of tetrahydrofuran, and the atmosphere inside the flask was replaced with nitrogen. The mixture was stirred at an internal temperature of 60 °C for 6 hours and then cooled to room temperature (20 °C). The reaction solution was then slowly added to a separatory funnel containing aqueous hydrochloric acid (a mixture of 6 g of 12 N hydrochloric acid and 54 g of water). After stirring for 30 minutes, the lower layer was recovered. The recovered solution was then heated at 110 °C / 1 mmHg to remove the solvent, yielding 35 g of compound (M-2). CF3OCF2CF2O-CF2CF2CF2CF2CF2CF2O(CF2CF2O-CF2CF2CF2CF2O) x13 CF2CF2OCF2CF2CF2C(OH)(CH2CH=CH2)2 formula (M-2)

[0144] (Example 13-3) 0.67 g of HO(C=O)C(CH2CH=CH2)3, 33 mL of dichloromethane, and 0.67 mL of oxalyl chloride were added to a 200 cc recovery flask and stirred under ice cooling, followed by the addition of 0.0393 g of DMF (N,N-dimethylformamide). After stirring at room temperature for 3 hours, the mixture was concentrated to obtain 0.6 g of Cl(C=O)C(CH2CH=CH2)3. Separately, 7 g of compound (M-2), 7 g of AC6000, 0.4 g of triethylamine, 0.2 g of N,N-dimethyl-4-aminopyridine, and 0.6 g of the above Cl(C=O)C(CH2CH=CH2)3 were added to a 50 cc recovery flask, and the mixture was stirred at 60°C for 20 hours. The obtained crude product was purified by silica gel chromatography to obtain 5.8 g of compound (M-3). CF3OCF2CF2O-CF2CF2CF2CF2CF2CF2O(CF2CF2O-CF2CF2CF2CF2O) x13CF2CF2OCF2CF2CF2C[O(C=O)C(CH2CH=CH2)3](CH2CH=CH2)2 formula (M-3)

[0145] (Example 13-4) A 50 cc recovery flask purged with nitrogen was charged with 1.0 g of compound (M-3), 0.003 g of a xylene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass), 0.0009 g of aniline, and 1.0 g of AC6000, followed by 0.22 g of trimethoxysilane and stirring for 4 hours at 40° C. The same amount of a xylene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass), aniline, and AC6000 were then added and stirred for 7 hours. The solvent was then distilled off, yielding 1.1 g of compound (1-M) (yield: 95%). CF3OCF2CF2O-CF2CF2CF2CF2CF2CF2O(CF2CF2O-CF2CF2CF2CF2O) x13 CF2CF2OCF2CF2CF2C[O(C=O)C(CH2CH2CH2Si(OCH3)3)3](CH2CH2CH2Si(OCH3)3) 2 types (1-M) Average value of number of units x 13: 9.

[0146] [Example 14] (Example 14-1) Compound (1-N) was synthesized in the same manner as in Synthesis Examples 13-3 and 13-4, except that HO(C=O)C(CH2CH=CH2)3 in Example 13-3 was changed to HO(C=O)CH(CH2CH=CH2)2. CF3OCF2CF2O-CF2CF2CF2CF2CF2CF2O(CF2CF2O-CF2CF2CF2CF2O) x14 CF2CF2OCF2CF2CF2C[O(C=O)CH(CH2CH2CH2Si(OCH3)3)2](CH2CH2CH2Si(OCH3)3)2 Formula (1-N) Average value of number of units x 14: 9.

[0147] [Example 15] (Example 15-1) Compound (1-O) was synthesized in the same manner as in Synthesis Examples 13-3 and 13-4, except that HO(C=O)C(CH2CH=CH2)3 in Example 13-3 was changed to HO(C=O)CH2CH=CH2. CF3OCF2CF2O-CF2CF2CF2CF2CF2CF2O(CF2CF2O-CF2CF2CF2CF2O) x15 CF2CF2OCF2CF2CF2C[O(C=O)CH2CH2CH2Si(OCH3)3](CH2CH2CH2Si(OCH3)3)2 Formula (1-O) Average value of units x 15: 9.

[0148] [Example 16] (Example 16-1) Compound (1-P) was synthesized in the same manner as in Synthesis Examples 13-1 to 13-4, except that compound (M-1) in Example 13-2 was changed to compound (G-1). CF3CF2CF2-O-CF2-CF2OCF2CF2CF2CF2CF2CF2O-CF2-CF2-{(OCF2) x16 (OCF2CF2) y16}-OCF2-C[O(C=O)C(CH2CH2CH2Si(OCH3)3)3](CH2CH2CH2Si(OCH3)3)2 formula (1-P) Average value of x16: 26, average value of y16: 22.

[0149] [Example 17] (Example 17-1) Compound (1-Q) was synthesized in the same manner as in Example 14, except that compound (M-1) in Example 14 was changed to compound (G-1). CF3CF2CF2-O-CF2-CF2OCF2CF2CF2CF2CF2CF2O-CF2-CF2-{(OCF2) x17 (OCF2CF2) y17}-OCF2-C[O(C=O)CH(CH2CH2CH2Si(OCH3)3)2](CH2CH2CH2Si(OCH3)3)2 formula (1-Q) Average value of x17: 26, average value of y17: 22.

[0150] [Example 18] (Example 18-1) Compound (1-R) ​​was synthesized in the same manner as in Synthesis Example 15, except that compound (M-1) in Example 15-1 was changed to compound (G-1). CF3CF2CF2-O-CF2-CF2OCF2CF2CF2CF2CF2CF2O-CF2-CF2-{(OCF2) x18 (OCF2CF2) y18}-OCF2-C[O(C=O)CH2CH2CH2Si(OCH3)3](CH2CH2CH2Si(OCH3)3)2 Formula (1-R) Average value of x18: 26, average value of y18: 22.

[0151] [Example 19] (Example 19-1) 3.0 g of the following compound (S-1), 0.55 g of HO-CHC(CHCH=CH) , 0.14 g of NaF, and 3.0 g of AC2000 were placed in a 50 ml recovery flask and stirred for 5 hours at 30° C. The obtained crude product was purified by silica gel chromatography to obtain 2.5 g of the following compound (S-2). CF3(OCF2CF2OCF2CF2CF2CF2) x19 OC(=O)CF(CF3)OCF2CF2CF3 formula (S-1)

[0152] CF3(OCF2CF2OCF2CF2CF2CF2) x19 OCF2CF2OCF2CF2CF2C(=O)OCH2C(CH2CH=CH2)3 formula (S-2) x19 average value: 13.

[0153] (Example 19-2) A 50 cc recovery flask purged with nitrogen was charged with 1.0 g of compound S-2, 0.003 g of a xylene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass), 0.0009 g of aniline, and 1.0 g of AC6000, followed by 0.11 g of trimethoxysilane and stirring for 4 hours at 40° C. The same amount of a xylene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass), aniline, and AC6000 were then added and stirred for 7 hours. The solvent was then distilled off to obtain 1.1 g of compound (1-S) (yield: 95%). CF3(OCF2CF2OCF2CF2CF2CF2) x19 OCF2CF2OCF2CF2CF2C(=O)OCH2C(CH2CH2CH2Si(OCH3)3)3 formula (1-S) x19 average value: 13.

[0154] [Example 20] (Example 20-1) Compound (X-1) was obtained according to the method described in the comparative example of JP-A-2007-204586. F(CF2CF2CF2O) x20 CF2CF2COF formula (X-1) x20 average value: 26.

[0155] (Example 20-2) 20 g of compound (X-1), 1.8 g of sodium fluoride, and 20 mL of AC-2000 were placed in a 50 mL recovery flask and stirred in an ice bath. 1.4 g of methanol was added and stirred at 25°C for 1 hour. After filtration, the filtrate was purified by column chromatography to obtain 14 g of compound (X-2). F(CF2CF2CF2O) x20 CF2CF2C(=O)OCH3 formula (X-2) x20 average value: 26.

[0156] (Example 20-3) The following compound (1-X) was obtained in the same manner as in Example 1-2, except that the compound (A-1) in Example 1-2 was changed to the compound (X-2). F(CF2CF2CF2O) x20 CF2CF2CH2O(C=O)C[CH2CH2CH2Si(OCH3)3]3 formula (1-X) x20 average value: 26.

[0157] [Example 21] (Example 21-1) 20 g of CHMINOX PO-M-AF (manufactured by Unimatex), 1.8 g of sodium fluoride, and 20 mL of AC-2000 were placed in a 50 mL recovery flask and stirred in an ice bath. 1.8 g of methanol was added and stirred at 25°C for 1 hour. After filtration, the filtrate was purified by column chromatography. 14 g of compound (Y-1) was obtained. CF3CF2CF2O(CF(CF3)CF2O) x21 CF(CF3)C(=O)OCH3 Formula (Y-1) x21 average value: 14.

[0158] (Example 21-2) The following compound (1-Y) was obtained in the same manner as in Example 1-2, except that the compound (A-1) in Example 1-2 was changed to the compound (Y-1). CF3CF2CF2O(CF(CF3)CF2O) x21 CF(CF3)CH2O(C=O)C[CH2CH2CH2Si(OCH3)3]3 formula (1-Y) x21 average value: 14.

[0159] [Production and evaluation of goods] Substrates were surface-treated using each of the compounds obtained in Examples 1 to 21 to produce articles. The surface treatment method used in each example was the dry coating method or wet coating method described below. Chemically strengthened glass was used as the substrate. The resulting articles were evaluated by the following methods. The results are shown in Table 1.

[0160] (Dry coating method) Dry coating was carried out using a vacuum deposition apparatus (VTR350M, manufactured by ULVAC Corporation) (vacuum deposition method). 0.5 g of each of the compounds obtained in Examples 1 to 21 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 compound 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 compound had been deposited was heat-treated at 200°C for 30 minutes and washed with dichloropentafluoropropane (AK-225, manufactured by AGC Corporation), yielding an article having a surface layer on the surface of the substrate.

[0161] (wet coating method) Each compound obtained in Examples 1 to 21 was mixed with C4F9OC2H5 (3M, Novec (registered trademark) 7200) as a 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 layer on the surface of the substrate.

[0162] (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.

[0163] <Abrasion resistance (steel wool)> The surface layer was measured for its water contact angle using a reciprocating traverse tester (KNT Corporation) in accordance with JIS L0849:2013 (ISO 105-X12:2001) by rubbing steel wool Bonstar (#0000) back and forth 15,000 times at a pressure of 98.07 kPa and a speed of 320 cm / min. The water contact angle was then measured using the method described above. The smaller the decrease in water repellency (water contact angle) after rubbing, the smaller the decrease in performance due to friction, and the more excellent the abrasion resistance. The evaluation criteria are as follows: ◎ (Excellent): The change in water contact angle after 15,000 reciprocating strokes is less than 2 degrees. ○ (Good): The change in water contact angle after 15,000 reciprocating strokes is more than 2 degrees and less than 5 degrees. △ (Acceptable): The change in water contact angle after 15,000 reciprocating strokes is more than 5 degrees and less than 10 degrees. × (Unacceptable): The change in water contact angle after 15,000 reciprocating strokes is more than 10 degrees.

[0164] <Acid resistance + abrasion resistance (steel wool)> The article was immersed in a 5N 60°C hydrochloric acid solution for 5 hours (acid treatment), then rinsed with water, air-dried, and then subjected to the steel wool test described above. The smaller the decrease in water contact angle after the test, the smaller the deterioration in performance due to acid, and the more excellent the acid resistance. The evaluation criteria are as follows: ◎ (Excellent): The change in water contact angle after acid treatment plus 15,000 reciprocating strokes is 2 degrees or less. ◯ (Good): After acid treatment and 15,000 reciprocating strokes, the change in water contact angle is more than 2 degrees and less than 5 degrees. △ (Acceptable): After acid treatment and 15,000 reciprocating strokes, the change in water contact angle is more than 5 degrees and less than 10 degrees. × (Not acceptable): The change in water contact angle after acid treatment and 15,000 reciprocating cycles exceeds 10 degrees.

[0165] <Fingerprint removal> An artificial fingerprint liquid (a liquid consisting of oleic acid and squalene) was applied to the flat surface of a silicone rubber stopper, and excess oil was wiped off with a nonwoven fabric (Bencotto (registered trademark) M-3, manufactured by Asahi Kasei Corporation) to prepare a fingerprint stamp. 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 load of 4.9 N using a reciprocating traverse tester (manufactured by KNT Corporation) equipped with tissue paper. 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.

[0166] [Table 1]

[0167] As shown in Table 1, the fluorine-containing ether compounds of Examples 1 to 18, which have a polyfluoropolyether chain, a reactive silyl group, and a linking group containing a group represented by *-OC(=O)-**, and which have a structure in which the polyfluoropolyether chain located on the * side and the reactive silyl group located on the ** side are linked via the linking group, were shown to have particularly excellent acid resistance compared to the fluorine-containing ether compound of Example 19, which has a structure in which the polyfluoropolyether chain located on the ** side and the reactive silyl group located on the * side are linked. Thus, it was revealed that this compound has excellent chemical stability and can form a surface layer with excellent durability. [Industrial Applicability]

[0168] Articles having a surface layer containing the present compound are useful as, for example, optical articles used as parts of the following products, touch panels, anti-reflective films, anti-reflective glass, SiO2-treated glass, tempered glass, sapphire glass, quartz substrates, mold metals, etc. Products: car navigation systems, mobile phones, digital cameras, digital video cameras, personal digital assistants (PDAs), portable audio players, car audio, game equipment, eyeglass lenses, camera lenses, lens filters, sunglasses, medical equipment (gastroscopes, etc.), copiers, personal computers (PCs), liquid crystal displays, organic light-emitting diode (OLED) displays, plasma displays, touch panel displays, protective films, anti-reflective films, anti-reflective glass, nanoimprint templates, molds, etc.

[0169] This application claims priority based on Japanese Patent Application No. 2019-235862, filed December 26, 2019, the disclosure of which is incorporated herein by reference in its entirety. [Explanation of symbols]

[0170] 10: Base material with undercoat layer, 12: Base material, 14: Undercoat layer, 20: Article, 22: Surface layer

Claims

1. A surface treatment agent comprising a fluorine-containing ether compound represented by the following formula 1A: R ｆａ -R １ -O-C(=O)-Q １ {-T} ｇ Formula 1A however, R １ represents a linear alkylene group having 1 to 10 carbon atoms which may have, as a substituent, an alkyl group, an aryl group, an alkoxy group, or a hydroxyl group, which may have an oxygen atom or a silicon atom between the carbon atoms, Q １ is a (g+1)-valent organic group represented by any one of the following formulae (Q1), (Q2), and (Q5) to (Q7), which has a carbon atom bonded to —O—C(═O)— in formula 1, T is -Si(R) ３－ａ (L) ａ When two or more T's are present, the two or more T's may be the same or different, R is an alkyl group, L represents a hydrolyzable group selected from an alkoxy group, an aryloxy group, a halogen atom, an acyl group, an acyloxy group, and an isocyanate group, or a hydroxyl group, and two or more Ls in T may be the same or different; a is 2 or 3; g is an integer of 1 or greater; R ｆａ is a group represented by the following formula g1a: R ｆ１ -(OR ｆ２ ) ｍ１ -(O) ｎ１ - Formula g1a however, R ｆ１ represents a fluoroalkyl group having 1 to 20 carbon atoms or a monovalent fluorinated hydrocarbon group having a fluorinated alicyclic structure, R ｆ２ represents a fluoroalkylene group having 1 to 6 carbon atoms or a divalent fluorinated hydrocarbon group having a fluorinated alicyclic structure, m1 is an integer from 0 to 500, When m1 is 2 or more, (OR ｆ２ ) ｍ１ is two or more types OR ｆ２ and n1 is 0 or 1, 【Chemistry 1】 -A １ -C(R ｅ２ ) ３－ｇ３ (-Q ２２ -) ｇ３ Formula (Q2) -A ２ -Yes (R) ｅ３ ) ３－ｇ３ (-Q ２５ -) ｇ３ formula (Q5) -A １ -Q ２６ - Formula (Q6) -A １ -CH(-Q ２２ -)-Si(R ｅ３ ) ３－ｇ５ (-Q ２５ -) ｇ５ Formula (Q7) However, in the formulas (Q1) to (Q7), A １ Or, A 2 side is connected to —O—C(═O)— in formula 1, and Q ２２ , Q ２５ or Q ２６ The side connects to the T, A １ represents a single bond, an alkylene group, or an alkylene group having two or more carbon atoms and having —C(O)— or —O— between carbon atoms, A ２ is an alkylene group or a group having —C(O)— or —O— between carbon atoms in an alkylene group having two or more carbon atoms, Q １１ represents a single bond, —O—, an alkylene group, or an alkylene group having two or more carbon atoms and having —C(O)— or —O— between carbon atoms, Q ２２ is an alkylene group, a group having —C(O)— or —O— between carbon atoms of an alkylene group having 2 or more carbon atoms, a group having —C(O)— or —O— at the end of the alkylene group not connected to T, or a group having —C(O)— or —O— between carbon atoms of an alkylene group having 2 or more carbon atoms and also having —C(O)— or —O— at the end of the alkylene group not connected to T, １ GaQ ２２ If there are two or more, there are two or more Q ２２ may be the same or different, Q ２５ is an alkylene group or a group having —C(O)— or —O— between carbon atoms in an alkylene group having 2 or more carbon atoms, and Q １ GaQ ２５ If there are two or more, there are two or more Q ２５ may be the same or different, Q ２６ is an alkylene group or a group having —C(O)— or —O— between carbon atoms in an alkylene group having two or more carbon atoms, R ｅ１ is a hydrogen atom or an alkyl group, and Q １ is R ｅ１ When there are two or more R ｅ１ may be the same or different, R ｅ２ is a hydrogen atom, a hydroxyl group, an alkyl group, or an acyloxy group, R ｅ３ is an alkyl group, g1 is an integer of 0 to 3, g2 is an integer of 0 to 3, and g1+g2 is an integer of 1 to 6; g3 is an integer from 1 to 3, g5 is an integer from 0 to 3.

2. A surface treatment composition containing one or more fluorine-containing ether compounds represented by the following formula 1A and another fluorine-containing ether compound. R fa -R 1 -O-C(=O)-Q 1 {-T} g Formula 1A however, R 1 is a C 1-10 linear alkylene group which may have, as a substituent, an alkyl group, an aryl group, an alkoxy group, or a hydroxyl group, which may have an oxygen atom or a silicon atom between carbon atoms; Q 1 is a (g+1)-valent organic group represented by any one of the following formulae (Q1), (Q2), and (Q5) to (Q7), which has a carbon atom bonded to —O—C(═O)— in formula 1: T is —Si(R) 3-a (L) a , and when there are two or more Ts, the two or more Ts may be the same or different; R is an alkyl group, L represents a hydrolyzable group selected from an alkoxy group, an aryloxy group, a halogen atom, an acyl group, an acyloxy group, and an isocyanate group, or a hydroxyl group, and two or more Ls in T may be the same or different; a is 2 or 3; g is an integer of 1 or greater; R fa is a group represented by the following formula g1a: R f1 -(OR f2 ) m1 -(O) n1 - Formula g1a however, R f1 is a fluoroalkyl group having 1 to 20 carbon atoms or a monovalent fluorinated hydrocarbon group having a fluorinated alicyclic structure, R f2 is a fluoroalkylene group having 1 to 6 carbon atoms or a divalent fluorinated hydrocarbon group having a fluorinated alicyclic structure, m1 is an integer from 0 to 500, When m1 is 2 or more, (OR f2 ) m1 may consist of two or more types of OR f2 , n1 is 0 or 1, 【Chemistry 2】 -A 1 -C(R e2 ) 3-g3 (-Q 22 -) g3 Formula (Q2) -A 2 -Si(R e3 ) 3-g3 (-Q 25 -) g3 Formula (Q5) -A 1 -Q 26 - Formula (Q6) -A 1 -CH(-Q 22 -)-Si(R e3 ) 3-g5 (-Q 25 -) g5 Formula (Q7) In the formulae (Q1) to (Q7), A 1 or A 2 is connected to —O—C(═O)— in formula 1, and Q 22 , Q 25 or Q 26 is connected to T; A 1 is a single bond, an alkylene group, or an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— between carbon atoms; A 2 is an alkylene group or an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— between carbon atoms, Q 11 is a single bond, —O—, an alkylene group, or an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— between carbon atoms; Q 22 is an alkylene group, a group having —C(O)— or —O— between carbon-carbon atoms of an alkylene group having 2 or more carbon atoms, a group having —C(O)— or —O— at the end of the alkylene group not connected to T, or a group having —C(O)— or —O— between carbon-carbon atoms of an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— at the end of the side not connected to T, and when Q 1 has two or more Q 22 , the two or more Q 22 may be the same or different, Q 25 represents an alkylene group or an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— between carbon atoms, and when Q 1 has two or more Q 25 s, the two or more Q 25 s may be the same or different; Q 26 is an alkylene group or an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— between carbon atoms; R e1 represents a hydrogen atom or an alkyl group, and when Q 1 has two or more R e1 s, the two or more R e1 s may be the same or different; R e2 is a hydrogen atom, a hydroxyl group, an alkyl group, or an acyloxy group; R e3 is an alkyl group; g1 is an integer of 0 to 3, g2 is an integer of 0 to 3, and g1+g2 is an integer of 1 to 6; g3 is an integer from 1 to 3, g5 is an integer from 0 to 3.

3. A fluorine-containing ether compound represented by the following formula 1A or the surface treatment agent composition according to claim 2, A coating liquid containing a liquid medium. R fa -R 1 -O-C(=O)-Q 1 {-T} g Formula 1A however, R 1 is a C 1-10 linear alkylene group which may have, as a substituent, an alkyl group, an aryl group, an alkoxy group, or a hydroxyl group, which may have an oxygen atom or a silicon atom between carbon atoms; Q 1 is a (g+1)-valent organic group represented by any one of the following formulae (Q1), (Q2), and (Q5) to (Q7), which has a carbon atom bonded to —O—C(═O)— in formula 1: T is —Si(R) 3-a (L) a , and when there are two or more Ts, the two or more Ts may be the same or different; R is an alkyl group, L represents a hydrolyzable group selected from an alkoxy group, an aryloxy group, a halogen atom, an acyl group, an acyloxy group, and an isocyanate group, or a hydroxyl group, and two or more Ls in T may be the same or different; a is 2 or 3; g is an integer of 1 or greater; R fa is a group represented by the following formula g1a: R f1 -(OR f2 ) m1 -(O) n1 - Formula g1a however, R f1 is a fluoroalkyl group having 1 to 20 carbon atoms or a monovalent fluorinated hydrocarbon group having a fluorinated alicyclic structure, R f2 is a fluoroalkylene group having 1 to 6 carbon atoms or a divalent fluorinated hydrocarbon group having a fluorinated alicyclic structure, m1 is an integer from 0 to 500, When m1 is 2 or more, (OR f2 ) m1 may consist of two or more types of OR f2 , n1 is 0 or 1, 【Transformation 3】 -A 1 -C(R e2 ) 3-g3 (-Q 22 -) g3 Formula (Q2) -A 2 -Si(R e3 ) 3-g3 (-Q 25 -) g3 Formula (Q5) -A 1 -Q 26 - Formula (Q6) -A 1 -CH(-Q 22 -)-Si(R e3 ) 3-g5 (-Q 25 -) g5 Formula (Q7) In the formulae (Q1) to (Q7), A 1 or A 2 is connected to —O—C(═O)— in formula 1, and Q 22 , Q 25 or Q 26 is connected to T; A 1 is a single bond, an alkylene group, or an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— between carbon atoms; A 2 is an alkylene group or an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— between carbon atoms, Q 11 is a single bond, —O—, an alkylene group, or an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— between carbon atoms; Q 22 is an alkylene group, a group having —C(O)— or —O— between carbon-carbon atoms of an alkylene group having 2 or more carbon atoms, a group having —C(O)— or —O— at the end of the alkylene group not connected to T, or a group having —C(O)— or —O— between carbon-carbon atoms of an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— at the end of the side not connected to T, and when Q 1 has two or more Q 22 , the two or more Q 22 may be the same or different, Q 25 represents an alkylene group or an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— between carbon atoms, and when Q 1 has two or more Q 25 s, the two or more Q 25 s may be the same or different; Q 26 is an alkylene group or an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— between carbon atoms; R e1 represents a hydrogen atom or an alkyl group, and when Q 1 has two or more R e1 s, the two or more R e1 s may be the same or different; R e2 is a hydrogen atom, a hydroxyl group, an alkyl group, or an acyloxy group; R e3 is an alkyl group; g1 is an integer of 0 to 3, g2 is an integer of 0 to 3, and g1+g2 is an integer of 1 to 6; g3 is an integer from 1 to 3, g5 is an integer from 0 to 3.

4. An article having a surface layer formed from a fluorine-containing ether compound represented by the following formula 1A or the surface treatment agent composition described in claim 2. R fa -R 1 -O-C(=O)-Q 1 {-T} g Formula 1A however, R 1 is a C 1-10 linear alkylene group which may have, as a substituent, an alkyl group, an aryl group, an alkoxy group, or a hydroxyl group, which may have an oxygen atom or a silicon atom between carbon atoms; Q 1 is a (g+1)-valent organic group represented by any one of the following formulae (Q1), (Q2), and (Q5) to (Q7), which has a carbon atom bonded to —O—C(═O)— in formula 1: T is —Si(R) 3-a (L) a , and when there are two or more Ts, the two or more Ts may be the same or different; R is an alkyl group, L represents a hydrolyzable group selected from an alkoxy group, an aryloxy group, a halogen atom, an acyl group, an acyloxy group, and an isocyanate group, or a hydroxyl group, and two or more Ls in T may be the same or different; a is 2 or 3; g is an integer of 1 or greater; R fa is a group represented by the following formula g1a: R f1 -(OR f2 ) m1 -(O) n1 - Formula g1a however, R f1 is a fluoroalkyl group having 1 to 20 carbon atoms or a monovalent fluorinated hydrocarbon group having a fluorinated alicyclic structure, R f2 is a fluoroalkylene group having 1 to 6 carbon atoms or a divalent fluorinated hydrocarbon group having a fluorinated alicyclic structure, m1 is an integer from 0 to 500, When m1 is 2 or more, (OR f2 ) m1 may consist of two or more types of OR f2 , n1 is 0 or 1, 【Chemistry 4】 -A 1 -C(R e2 ) 3-g3 (-Q 22 -) g3 Formula (Q2) -A 2 -Si(R e3 ) 3-g3 (-Q 25 -) g3 Formula (Q5) -A 1 -Q 26 - Formula (Q6) -A 1 -CH(-Q 22 -)-Si(R e3 ) 3-g5 (-Q 25 -) g5 Formula (Q7) In the formulae (Q1) to (Q7), A 1 or A 2 is connected to —O—C(═O)— in formula 1, and Q 22 , Q 25 or Q 26 is connected to T; A 1 is a single bond, an alkylene group, or an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— between carbon atoms; A 2 is an alkylene group or an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— between carbon atoms, Q 11 is a single bond, —O—, an alkylene group, or an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— between carbon atoms; Q 22 is an alkylene group, a group having —C(O)— or —O— between carbon-carbon atoms of an alkylene group having 2 or more carbon atoms, a group having —C(O)— or —O— at the end of the alkylene group not connected to T, or a group having —C(O)— or —O— between carbon-carbon atoms of an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— at the end of the side not connected to T, and when Q 1 has two or more Q 22 , the two or more Q 22 may be the same or different, Q 25 represents an alkylene group or an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— between carbon atoms, and when Q 1 has two or more Q 25 s, the two or more Q 25 s may be the same or different; Q 26 is an alkylene group or an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— between carbon atoms; R e1 represents a hydrogen atom or an alkyl group, and when Q 1 has two or more R e1 s, the two or more R e1 s may be the same or different; R e2 is a hydrogen atom, a hydroxyl group, an alkyl group, or an acyloxy group; R e3 is an alkyl group; g1 is an integer of 0 to 3, g2 is an integer of 0 to 3, and g1+g2 is an integer of 1 to 6; g3 is an integer from 1 to 3, g5 is an integer from 0 to 3.

5. A method for manufacturing an article, comprising forming a surface layer by a dry coating method or a wet coating method using a fluorine-containing ether compound represented by the following formula 1A, or the surface treatment agent composition described in claim 2, or the coating liquid described in claim 3. R fa -R 1 -O-C(=O)-Q 1 {-T} g Formula 1A however, R 1 is a C 1-10 linear alkylene group which may have, as a substituent, an alkyl group, an aryl group, an alkoxy group, or a hydroxyl group, which may have an oxygen atom or a silicon atom between carbon atoms; Q 1 is a (g+1)-valent organic group represented by any one of the following formulae (Q1), (Q2), and (Q5) to (Q7), which has a carbon atom bonded to —O—C(═O)— in formula 1: T is —Si(R) 3-a (L) a , and when there are two or more Ts, the two or more Ts may be the same or different; R is an alkyl group, L represents a hydrolyzable group selected from an alkoxy group, an aryloxy group, a halogen atom, an acyl group, an acyloxy group, and an isocyanate group, or a hydroxyl group, and two or more Ls in T may be the same or different; a is 2 or 3; g is an integer of 1 or greater; R fa is a group represented by the following formula g1a: R f1 -(OR f2 ) m1 -(O) n1 - Formula g1a however, R f1 is a fluoroalkyl group having 1 to 20 carbon atoms or a monovalent fluorinated hydrocarbon group having a fluorinated alicyclic structure, R f2 is a fluoroalkylene group having 1 to 6 carbon atoms or a divalent fluorinated hydrocarbon group having a fluorinated alicyclic structure, m1 is an integer from 0 to 500, When m1 is 2 or more, (OR f2 ) m1 may consist of two or more types of OR f2 , n1 is 0 or 1, 【Transformation 5】 -A 1 -C(R e2 ) 3-g3 (-Q 22 -) g3 Formula (Q2) -A 2 -Si(R e3 ) 3-g3 (-Q 25 -) g3 Formula (Q5) -A 1 -Q 26 - Formula (Q6) -A 1 -CH(-Q 22 -)-Si(R e3 ) 3-g5 (-Q 25 -) g5 Formula (Q7) In the formulae (Q1) to (Q7), A 1 or A 2 is connected to —O—C(═O)— in formula 1, and Q 22 , Q 25 or Q 26 is connected to T; A 1 is a single bond, an alkylene group, or an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— between carbon atoms; A 2 is an alkylene group or an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— between carbon atoms, Q 11 is a single bond, —O—, an alkylene group, or an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— between carbon atoms; Q 22 is an alkylene group, a group having —C(O)— or —O— between carbon-carbon atoms of an alkylene group having 2 or more carbon atoms, a group having —C(O)— or —O— at the end of the alkylene group not connected to T, or a group having —C(O)— or —O— between carbon-carbon atoms of an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— at the end of the side not connected to T, and when Q 1 has two or more Q 22 , the two or more Q 22 may be the same or different, Q 25 represents an alkylene group or an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— between carbon atoms, and when Q 1 has two or more Q 25 s, the two or more Q 25 s may be the same or different; Q 26 is an alkylene group or an alkylene group having 2 or more carbon atoms and having —C(O)— or —O— between carbon atoms; R e1 represents a hydrogen atom or an alkyl group, and when Q 1 has two or more R e1 s, the two or more R e1 s may be the same or different; R e2 is a hydrogen atom, a hydroxyl group, an alkyl group, or an acyloxy group; R e3 is an alkyl group; g1 is an integer of 0 to 3, g2 is an integer of 0 to 3, and g1+g2 is an integer of 1 to 6; g3 is an integer from 1 to 3, g5 is an integer from 0 to 3.

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