WO2025013831A1 - Composé contenant un groupe fluoropolyéther - Google Patents

Composé contenant un groupe fluoropolyéther Download PDF

Info

Publication number
WO2025013831A1
WO2025013831A1 PCT/JP2024/024633 JP2024024633W WO2025013831A1 WO 2025013831 A1 WO2025013831 A1 WO 2025013831A1 JP 2024024633 W JP2024024633 W JP 2024024633W WO 2025013831 A1 WO2025013831 A1 WO 2025013831A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
integer
independently
formula
fluorine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/JP2024/024633
Other languages
English (en)
Japanese (ja)
Inventor
健介 茂原
恒雄 山下
大貴 久保田
孝之 荒木
尚志 三橋
ジョンヒョク 李
ガヨン 李
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Daikin Industries Ltd
Original Assignee
Daikin Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Daikin Industries Ltd filed Critical Daikin Industries Ltd
Priority to KR1020267000071A priority Critical patent/KR20260018148A/ko
Priority to CN202480046133.4A priority patent/CN121464168A/zh
Publication of WO2025013831A1 publication Critical patent/WO2025013831A1/fr
Anticipated expiration legal-status Critical
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
    • C08G65/325—Polymers modified by chemical after-treatment with inorganic compounds containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/16—Antifouling paints; Underwater paints
    • C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
    • C09D5/1637—Macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/18—Coatings for keeping optical surfaces clean, e.g. hydrophobic or photo-catalytic films
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
    • C08G2650/46—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing halogen
    • C08G2650/48—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing halogen containing fluorine, e.g. perfluropolyethers

Definitions

  • This disclosure relates to fluoropolyether group-containing compounds.
  • the objective is to provide a fluorine-containing compound that has excellent solubility in solvents.
  • Each R2 is independently a hydrocarbon group;
  • Each R A is independently a group containing -OCO-CR 3 ⁇ CH 2 ;
  • Each R3 is independently a hydrogen atom or a hydrocarbon group;
  • R B is a monovalent or divalent group containing a fluoropolyether group,
  • Each R is independently a hydrogen atom or a monovalent group;
  • a is 1 or 2.
  • a fluorine-containing compound represented by the formula: [2] The fluorine-containing compound according to the above [1], wherein R 1 is O or S.
  • X A1 is -R A11 -R A12 -, or -R A13 (-R A12 ) 2 ;
  • R A11 is a C 1-20 alkylene group, -(CH 2 ) z1 -O-(CH 2 ) z2 - (wherein z1 is an integer from 0 to 10, and z2 is an integer from 0 to 10), or -(CH 2 ) z3 -phenylene-(CH 2 ) z4 - (wherein z3 is an integer from 0 to 10, and z4 is an integer from 0 to 10);
  • R A12 is —O—, —CO—, or —NR 11 —;
  • R 11 is a hydrogen atom or a hydrocarbon group;
  • R A13 is a trivalent C 1-10 hydrocarbon group or a trivalent C 1-10 hydrocarbon group containing one or more O in the main chain.
  • X A2 is -X A3 (-X A4 ) A3 ;
  • X A3 is a single bond or a divalent or trivalent organic group;
  • A3 is the valence of X A3 minus 1;
  • Each X A4 is independently a divalent or trivalent organic group.
  • X A3 is a single bond, —R A31 —R A32 —, or —R A33 (—R A32 ) 2 ;
  • R A31 is a C 1-20 alkylene group, -(CH 2 ) z5 -O-(CH 2 ) z6 - (wherein z5 is an integer of 0 to 10, and z6 is an integer of 0 to 10), or -(CH 2 ) z7 -phenylene-(CH 2 ) z8 - (wherein z7 is an integer of 0 to 10, and z8 is an integer of 0 to 10);
  • R A32 is —O—, —CO—, or —NR 12 —;
  • R 12 is a hydrogen atom or a hydrocarbon group;
  • R A33 is a trivalent hydrocarbon group or a trivalent C 1-10 hydrocarbon group containing one or more O in the main chain;
  • X A4 is —CO—NH—C(R 13 ) 3-a4 (R 14 ) a4 ;
  • R 13 is a hydrogen atom or a C 1-6 alkyl group;
  • Each R 14 is independently a C 1-6 alkylene group;
  • a4 is 1 or 2;
  • R B is -X B1 -R F1 or -X B1 -R F2 -X B1 -;
  • R F1 is a monovalent fluoropolyether group;
  • RF2 is a divalent fluoropolyether group;
  • Each X B1 independently represents a single bond or a divalent organic group;
  • the fluorine-containing compound according to any one of the above [1] to [8].
  • R F1 is Rf 1 -R F -O q -;
  • R F2 is -Rf 2 p -R F -O q -;
  • Rf1 is a C 1-16 alkyl group optionally substituted by one or more fluorine atoms;
  • Rf2 is a C 1-6 alkylene group optionally substituted by one or more fluorine atoms,
  • Each R F is independently a divalent fluoropolyether group;
  • p is 0 or 1;
  • Each q is independently 0 or 1;
  • Each R F independently represents the formula: -(OC 6 F 12 ) a -(OC 5 F 10 ) b -(OC 4 F 8 ) c -(OC 3 R Fa 6 ) d -(OC 2 F 4 ) e -(OCF 2 ) f - [Wherein: Each R Fa is independently a hydrogen atom, a fluorine atom, or a chlorine atom; a, b, c, d, e, and f each independently represent an integer of 0 to 200, the sum of a, b, c, d, e, and f is 1 or more, and the order of the repeating units enclosed in parentheses with a, b, c, d, e, or f is arbitrary in the formula.
  • R F each independently represents the following formula (f1), (f2), (f3), (f4), (f5), or (f6): -(OC 3 F 6 ) d - (OC 2 F 4 ) e - (f1) [In the formula, d is an integer of 1 to 200, and e is 0 or 1.] -(OC 4 F 8 ) c - (OC 3 F 6 ) d - (OC 2 F 4 ) e - (OCF 2 ) f - (f2) [In the formula, c and d each independently represent an integer of 0 to 30; e and f are each independently an integer from 1 to 200; The sum of c, d, e and f is an integer from 10 to 200; The
  • R6 is OCF2 or OC2F4 ;
  • R7 is a group selected from OC2F4 , OC3F6 , OC4F8 , OC5F10 and OC6F12 or a combination of two or three groups selected from these groups ;
  • R 9 is a single bond or a group selected from OCF 2 , OC 2 F 4 , OC 3 F 6 , OC 4 F 8 , OC 5 F 10 and OC 6 F 12 , or a combination of two or three groups selected from these groups;
  • g is an integer from 2 to 100.
  • R6 is OCF2 or OC2F4
  • R7 is a group selected from OC2F4 , OC3F6 , OC4F8 , OC5F10 and OC6F12 , or a combination of two or three groups independently selected from these groups
  • R6 ' is OCF2 or OC2F4
  • R 7′ is a group selected from OC 2 F 4 , OC 3 F 6 , OC 4 F 8 , OC 5 F 10 and OC 6 F 12 , or a combination of two or three groups independently selected from these groups
  • g is an integer from 2 to 100
  • g' is an integer from 2 to 100
  • Rr is (In the formula, * indicates the bond position.) is.]
  • Each R2 is independently a hydrocarbon group;
  • R OH is —R A11 —OH, —R A13 (OH) 2 , or —R A14 (—R A13 (OH) 2 ) 2 ;
  • R A11 is a C 1-20 alkylene group, -(CH 2 ) z1 -O-(CH 2 ) z2 - (wherein z1 is an integer from 0 to 10, and z2 is an integer from 0 to 10), or -(CH 2 ) z3 -phenylene-(CH 2 ) z4 - (wherein z3 is an integer from 0 to 10, and z4 is an integer from 0 to 10);
  • R A13 is a trivalent C 1-10 hydrocarbon group or a trivalent C 1-10 hydrocarbon group containing one or more O in the main chain,
  • R A14 is
  • organic group refers to a monovalent group containing carbon. Unless otherwise specified, the monovalent organic group may be a hydrocarbon group or a derivative thereof. A derivative of a hydrocarbon group refers to a group having one or more N, O, S, Si, amide, sulfonyl, sulfoxide, siloxane, carbonyl, carbonyloxy, etc. at the end or in the molecular chain of the hydrocarbon group.
  • a “divalent organic group” refers to a divalent group containing carbon. Such a divalent organic group is not particularly limited, but includes a divalent group in which one hydrogen atom has been further removed from an organic group.
  • hydrocarbon group refers to a group containing carbon and hydrogen, and a group in which one hydrogen atom has been removed from a hydrocarbon.
  • hydrocarbon groups are not particularly limited, but include C 1-20 hydrocarbon groups, for example, aliphatic hydrocarbon groups, aromatic hydrocarbon groups, and the like.
  • the hydrocarbon group may be substituted with one or more substituents.
  • the above-mentioned "aliphatic hydrocarbon group” may be linear, branched, or cyclic, and may be saturated or unsaturated.
  • the hydrocarbon group may contain one or more ring structures.
  • substituents for a "hydrocarbon group” include, but are not limited to, one or more groups selected from a halogen atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 3-10 cycloalkyl group, a C 3-10 unsaturated cycloalkyl group, a 5-10 membered heterocyclyl group, a 5-10 membered unsaturated heterocyclyl group, a C 6-10 aryl group, and a 5-10 membered heteroaryl group, each of which may be substituted by one or more halogen atoms.
  • the present invention provides a fluorine-containing compound represented by the formula:
  • the compounds disclosed herein have excellent solubility in solvents, such as ketone-based solvents, ester-based solvents, and ether-based solvents, and are particularly excellent in ketone-based solvents.
  • R 1 is —O—, —S—, or —O—P( ⁇ O)(OR 2 )—, which improves the solubility of the fluorine-containing compound represented by formula (1).
  • Each R2 is independently a hydrocarbon group.
  • the hydrocarbon group is preferably a C1-6 alkyl group.
  • the C1-6 alkyl group may be linear or branched, and is preferably linear.
  • the C1-6 alkyl group is preferably a C1-4 alkyl group, and more preferably a methyl group.
  • R 1 is O or S, and preferably S.
  • R 1 is O or S, and particularly S, the solubility of the fluorine-containing compound represented by formula (1) is improved.
  • Each R A is independently a group containing -OCO-CR 3 ⁇ CH 2.
  • Each R 3 is independently a hydrogen atom or a hydrocarbon group.
  • the hydrocarbon group is preferably a C 1-6 alkyl group.
  • the C 1-6 alkyl group may be linear or branched, and is preferably linear.
  • the C 1-6 alkyl group is preferably a C 1-4 alkyl group, and more preferably a methyl group.
  • R3 is a hydrogen atom.
  • R3 is a hydrocarbon group, preferably a C1-6 alkyl group, more preferably a methyl group.
  • each R A is independently -X A1 (-X A2 (R Ac ) A2 ) A1 .
  • X A1 is a divalent to pentavalent organic group.
  • A1 is the valence of X A1 minus 1.
  • X A1 is preferably —R A11 —R A12 —, —R A13 (—R A12 ) 2 , or —R A14 (—R A13 (—R A12 ) 2 ) 2 .
  • X A1 is —R A11 -R A12 —.
  • X A1 is —R A13 (—R A12 ) 2 .
  • X A1 is —R A14 (—R A13 (—R A12 ) 2 ) 2 .
  • R A11 is a C 1-20 alkylene group, -(CH 2 ) z1 -O-(CH 2 ) z2 - (wherein z1 is an integer of 0 to 10, preferably an integer of 0 to 6, and z2 is an integer of 0 to 10, preferably an integer of 0 to 6), or -(CH 2 ) z3 -phenylene-(CH 2 ) z4 - (wherein z3 is an integer of 0 to 10, preferably an integer of 0 to 6, and z4 is an integer of 0 to 10, preferably an integer of 0 to 6).
  • the C 1-20 alkylene group may be linear or branched, preferably linear.
  • the C 1-20 alkyl group may be preferably a C 2-16 alkyl group, such as a C 4-16 alkyl group, a C 4-12 alkyl group, a C 6-12 alkyl group, or a C 6-10 alkyl group.
  • R A12 is —O—, —CO— or —NR 11 —.
  • R A12 is preferably —O—.
  • R 11 is a hydrogen atom or a hydrocarbon group.
  • the hydrocarbon group is preferably a C 1-6 alkyl group.
  • the C 1-6 alkyl group may be linear or branched, and is preferably linear.
  • the C 1-6 alkyl group is preferably a C 1-4 alkyl group, and more preferably a methyl group.
  • R A13 is a trivalent C 1-10 hydrocarbon group, or a group containing one or more O in the main chain of a trivalent C 1-10 hydrocarbon group.
  • a trivalent C 1-10 hydrocarbon group containing one or more O in the main chain is a group containing O at the terminal or between the carbon atoms in the main chain of the C 1-10 hydrocarbon group.
  • the trivalent C 1-10 hydrocarbon group may be linear, branched or cyclic, but is preferably branched.
  • the trivalent C 1-10 hydrocarbon group is preferably a C 3-10 hydrocarbon group, more preferably a C 3-8 hydrocarbon group.
  • R A13 is preferably a C 1-10 hydrocarbon group.
  • R A14 is a trivalent C 1-10 hydrocarbon group, or a group containing one or more O in the main chain of a trivalent C 1-10 hydrocarbon group.
  • a trivalent C 1-10 hydrocarbon group containing one or more O in the main chain is a group containing O at the terminal or between the carbon atoms in the main chain of the C 1-10 hydrocarbon group.
  • the trivalent C 1-10 hydrocarbon group may be linear, branched or cyclic, but is preferably branched.
  • the trivalent C 1-10 hydrocarbon group is preferably a C 3-10 hydrocarbon group, more preferably a C 3-8 hydrocarbon group.
  • R A14 is preferably a C 1-10 hydrocarbon group.
  • the C 1-10 hydrocarbon group having O bonded to both ends of R A13 can be represented by -C((CH 2 ) n O-) 2 (wherein n is independently an integer of 0 to 9, and the total number of n's is 9).
  • X A2 each independently represents a single bond or a divalent to pentavalent organic group.
  • A2 is the valence of X A2 minus 1.
  • X A2 is preferably —X A3 (—X A4 ) A3 .
  • X A3 is a single bond or a divalent or trivalent organic group.
  • A3 is the valence of X A3 minus 1.
  • X A3 is preferably a single bond, —R A31 —R A32 —, or —R A33 (—R A32 ) 2 .
  • R A31 is a C 1-20 alkylene group, -(CH 2 ) z5 -O-(CH 2 ) z6 - (wherein z5 is an integer of 0 to 10, preferably an integer of 0 to 6, and z6 is an integer of 0 to 10, preferably an integer of 0 to 6), or -(CH 2 ) z7 -phenylene-(CH 2 ) z8 - (wherein z7 is an integer of 0 to 10, preferably an integer of 0 to 6, and z8 is an integer of 0 to 10, preferably an integer of 0 to 6).
  • the C 1-20 alkylene group may be linear or branched, preferably linear.
  • the C 1-20 alkyl group may be preferably a C 2-16 alkyl group, such as a C 4-16 alkyl group, a C 4-12 alkyl group, a C 6-12 alkyl group, or a C 6-10 alkyl group.
  • R A32 is —O—, —CO— or —NR 12 —.
  • R A32 is preferably —O—.
  • R 12 is a hydrogen atom or a hydrocarbon group.
  • the hydrocarbon group is preferably a C 1-6 alkyl group.
  • the C 1-6 alkyl group may be linear or branched, and is preferably linear.
  • the C 1-6 alkyl group is preferably a C 1-4 alkyl group, and more preferably a methyl group.
  • R A33 is a trivalent hydrocarbon group, or a trivalent C 1-10 hydrocarbon group containing one or more O in the main chain.
  • the trivalent C 1-10 hydrocarbon group may be linear, branched or cyclic, but is preferably branched.
  • the trivalent C 1-10 hydrocarbon group is preferably a C 3-10 hydrocarbon group, more preferably a C 3-8 hydrocarbon group.
  • R A33 is preferably a C 1-10 hydrocarbon group.
  • Each X A4 is independently a divalent or trivalent organic group.
  • Each R Ac is independently -OCO-CR 3 ⁇ CH 2
  • each R 3 is independently a hydrogen atom or a hydrocarbon group.
  • Each X A4 independently represents a divalent or trivalent organic group.
  • X A4 is preferably —CO—NH—C(R 13 ) 3-a4 (R 14 ) a4 .
  • R 13 is a hydrogen atom or a C 1-6 alkyl group.
  • the C 1-6 alkyl group may be linear or branched, and is preferably linear.
  • the C 1-6 alkyl group is preferably a C 1-4 alkyl group, and more preferably a methyl group.
  • Each R 14 is independently a C 1-6 alkylene group.
  • the C 1-6 alkylene group may be linear or branched, and is preferably linear.
  • the C 1-6 alkylene group is preferably a C 1-4 alkylene group, and more preferably a methylene group.
  • a4 is 1 or 2.
  • a4 is 1.
  • a4 is 2.
  • R 1 B is a monovalent or divalent group containing a fluoropolyether group.
  • R 1 B is preferably —X B1 —R F1 or —X B1 —R F2 —X B1 —.
  • R F1 is a monovalent fluoropolyether group, preferably Rf 1 -R F -O q -.
  • R F2 is a divalent fluoropolyether group, preferably --Rf 2 p --R F --O q --.
  • Rf1 is a C 1-16 alkyl group optionally substituted with one or more fluorine atoms.
  • the "C 1-16 alkyl group" in the above-mentioned C 1-16 alkyl group optionally substituted by one or more fluorine atoms may be a straight chain or a branched chain, and is preferably a straight chain or branched chain C 1-6 alkyl group, particularly a C 1-3 alkyl group, and more preferably a straight chain C 1-6 alkyl group, particularly a C 1-3 alkyl group.
  • Rf 1 is preferably a C 1-16 alkyl group substituted by one or more fluorine atoms, more preferably a CF 2 H—C 1-15 perfluoroalkylene group, and even more preferably a C 1-16 perfluoroalkyl group.
  • the C 1-16 perfluoroalkyl group may be linear or branched, and is preferably a linear or branched C 1-6 perfluoroalkyl group, in particular a C 1-3 perfluoroalkyl group, and more preferably a linear C 1-6 perfluoroalkyl group, in particular a C 1-3 perfluoroalkyl group, specifically -CF 3 , -CF 2 CF 3 , or CF 2 CF 2 CF 3 .
  • Rf2 is a C 1-6 alkylene group optionally substituted with one or more fluorine atoms.
  • C 1-6 alkylene group in the above-mentioned C 1-6 alkylene group optionally substituted by one or more fluorine atoms may be a straight chain or a branched chain, and is preferably a straight chain or branched chain C 1-3 alkylene group, and more preferably a straight chain C 1-3 alkylene group.
  • Rf2 is preferably a C 1-6 alkylene group substituted by one or more fluorine atoms, more preferably a C 1-6 perfluoroalkylene group, and even more preferably a C 1-3 perfluoroalkylene group.
  • the above C 1-6 perfluoroalkylene group may be linear or branched, and is preferably a linear or branched C 1-3 perfluoroalkylene group, more preferably a linear C 1-3 perfluoroalkylene group, specifically, -CF 2 -, -CF 2 CF 2 -, or CF 2 CF 2 CF 2 -.
  • p is 0 or 1. In one embodiment, p is 0. In another embodiment, p is 1.
  • q is 0 or 1. In one embodiment, q is 0. In another embodiment, q is 1.
  • Each R 1 F is independently a divalent fluoropolyether group.
  • RF is preferably the following: -(OC h1 R Fa 2h1 ) h3 -(OC h2 R Fa 2h2-2 ) h4 - [Wherein: Each R Fa is independently a hydrogen atom, a fluorine atom, or a chlorine atom; h1 is an integer from 1 to 6, h2 is an integer from 4 to 8, h3 is an integer equal to or greater than 0; h4 is an integer equal to or greater than 0; However, the number of repeating units of h3 and h4 is 1 or more, preferably 2 or more, and more preferably 5 or more, and the order of the repeating units enclosed in parentheses with h3 and h4 is arbitrary in the formula. It may contain a group represented by:
  • RF can be linear or branched.
  • RF is preferably represented by the formula: -(OC 6 F 12 ) a -(OC 5 F 10 ) b -(OC 4 F 8 ) c -(OC 3 R Fa 6 ) d -(OC 2 F 4 ) e -(OCF 2 ) f -
  • Each R Fa is independently a hydrogen atom, a fluorine atom, or a chlorine atom
  • a, b, c, d, e, and f each independently represent an integer of 0 to 200, and the sum of a, b, c, d, e, and f is 1 or more.
  • the order of the repeating units enclosed in parentheses with a, b, c, d, e, or f is arbitrary in the formula.
  • It is a group represented by the following formula:
  • R Fa is preferably a hydrogen atom or a fluorine atom, and more preferably a fluorine atom.
  • a, b, c, d, e and f may each preferably be independently an integer from 0 to 100.
  • the sum of a, b, c, d, e and f is preferably 5 or more, more preferably 10 or more, and may be, for example, 15 or more or 20 or more.
  • the sum of a, b, c, d, e and f is preferably 200 or less, more preferably 100 or less, and even more preferably 60 or less, and may be, for example, 50 or less or 30 or less.
  • repeating units may be linear or branched.
  • the repeating unit may be - ( OC6F12 ) - , -( OCF2CF2CF2CF2CF2CF2CF2CF2 ) - , - (OCF( CF3 ) CF2CF2CF2CF2CF2 )-, - ( OCF2CF ( CF3 ) CF2CF2CF2 ) - , -(OCF2CF2CF ( CF3)CF2CF2CF2)- , - ( OCF2CF2CF2CF ( CF3 ) CF2CF2 )- , - ( OCF2CF2CF2CF2CF ( CF3 ) CF2 )- , -( OCF2CF2CF2CF2CF ( CF3 ) CF2 )- , -( OCF2CF2CF2CF2CF ( CF3 ) CF2 )-, and the like .
  • -(OC 5 F 10 )- is -(OCF 2 CF 2 CF 2 CF 2 CF 2 )-, -(OCF(CF 3 )CF 2 CF 2 CF 2 )-, -(OCF 2 CF(CF 3 )CF 2 CF 2 )-, -(OCF 2 CF 2 CF(CF 3 )CF 2 )-, -(OCF 2 CF 2 CF(CF 3 ))-, etc. may be used.
  • - ( OC4F8 )- may be any of -( OCF2CF2CF2CF2 )-, -(OCF( CF3 ) CF2CF2 ) -, - ( OCF2CF ( CF3 ) CF2 )-, - ( OCF2CF2CF ( CF3 ))-, -(OC(CF3)2CF2)-, -(OCF2C(CF3)2 ) - , - ( OCF ( CF3 )CF( CF3 )) - , -(OCF( C2F5 ) CF2 )- and ( OCF2CF ( C2F5 ))-.
  • -(OC 3 F 6 )- (i.e., in the above formula, R Fa is a fluorine atom) may be any of -(OCF 2 CF 2 CF 2 )-, -(OCF(CF 3 )CF 2 )-, and (OCF 2 CF(CF 3 ))-.
  • -(OC 2 F 4 )- may be any of -(OCF 2 CF 2 )- and (OCF(CF 3 ))-.
  • the repeating unit is linear. By making the repeating unit linear, the surface slip properties, friction durability, etc. of the surface treatment layer can be improved.
  • the repeating unit is branched. By making the repeating unit branched, the dynamic friction coefficient of the surface treatment layer can be increased.
  • R F can include a ring structure.
  • the ring structure may be a three-, four-, five-, or six-membered ring as described below. [In the formula, * indicates the bond position.]
  • the ring structure may preferably be a four-membered ring, a five-membered ring, or a six-membered ring, more preferably a four-membered ring or a six-membered ring.
  • the repeating unit having a ring structure may preferably be the following unit. [In the formula, * indicates the bond position.]
  • each R F is independently a group represented by any one of the following formulas (f1) to (f6).
  • -(OC 3 F 6 ) d - (OC 2 F 4 ) e - (f1) [In the formula, d is an integer from 1 to 200, and e is 0 or 1.]
  • c and d each independently represent an integer of 0 or more and 30 or less
  • e and f each independently represent an integer of 1 or more and 200 or less, the sum of c, d, e, and f is 2 or more;
  • the order of occurrence of each repeat unit enclosed in parentheses with the subscript c, d, e, or f is arbitrary in the formula.
  • R6 is OCF2 or OC2F4
  • R7 is a group selected from OC2F4 , OC3F6 , OC4F8 , OC5F10 and OC6F12 , or a combination of two or three groups independently selected from these groups
  • R 9 is a single bond or a group selected from OCF 2 , OC 2 F 4 , OC 3 F 6 , OC 4 F 8 , OC 5 F 10 and OC 6 F 12 , or a combination of two or three groups selected from these groups
  • g is an integer from 2 to 100
  • R6 is OCF2 or OC2F4
  • R7 is a group selected from OC2F4 , OC3F6 , OC4F8
  • d is preferably an integer of 5 to 200, more preferably 10 to 100, even more preferably 15 to 50, for example, an integer of 25 to 35.
  • e is 1.
  • (OC 3 F 6 ) is preferably a group represented by (OCF 2 CF 2 CF 2 ), (OCF 2 CF(CF 3 )) or (OCF(CF 3 )CF 2 ), more preferably a group represented by -(OCF 2 CF 2 CF 2 ) d -.
  • (OC 2 F 4 ) is a group represented by (OCF 2 CF 2 ) or (OCF(CF 3 )), preferably a group represented by (OCF 2 CF 2 ).
  • e and f are each independently preferably an integer of 5 or more and 200 or less, more preferably an integer of 10 to 200.
  • the sum of c, d, e and f is preferably 5 or more, more preferably 10 or more, and may be, for example, 15 or more or 20 or more.
  • the above formula (f2) is preferably a group represented by -(OCF 2 CF 2 CF 2 CF 2 ) c -(OCF 2 CF 2 CF 2 ) d -(OCF 2 CF 2 ) e -(OCF 2 ) f -.
  • the formula (f2) may be a group represented by -(OC 2 F 4 ) e -(OCF 2 ) f -.
  • R6 is preferably OC2F4 .
  • R7 is preferably a group selected from OC2F4 , OC3F6 , and OC4F8 , or a combination of two or three groups independently selected from these groups , and more preferably a group selected from OC3F6 and OC4F8 .
  • the combination of two or three groups independently selected from OC 2 F 4 , OC 3 F 6 and OC 4 F 8 is not particularly limited, and examples thereof include -OC 2 F 4 OC 3 F 6 -, -OC 2 F 4 OC 4 F 8 -, -OC 3 F 6 OC 2 F 4 -, -OC 3 F 6 OC 3 F 6 -, -OC 3 F 6 OC 4 F 8 -, -OC 4 F 8 OC 4 F 8 -, -OC 4 F 8 OC 3 F 6 -, -OC 4 F 8 OC 2 F 4 -, -OC 2 F 4 OC 2 F 4 OC 3 F 6 -, -OC 2 F 4 OC 2 F 4 OC 3 F 6 -, -OC 2 F 4 OC 2 F 4 OC 4 F 8 -, -OC 2 F 4 OC 3 F 6 -, -OC 2 F 4 OC 2 F 4 OC 4 F 8 -, -OC 2 F 4 OC 3 F 6 -,
  • g is preferably an integer of 3 or more, more preferably 5 or more.
  • the above g is preferably an integer of 50 or less.
  • OC 2 F 4 , OC 3 F 6 , OC 4 F 8 , OC 5 F 10 and OC 6 F 12 may be either linear or branched, and are preferably linear.
  • the above formula (f3) is preferably -(OC 2 F 4 -OC 3 F 6 ) g - or (OC 2 F 4 -OC 4 F 8 ) g -.
  • R 9 is a single bond.
  • R 9 is a group selected from OCF 2 , OC 2 F 4 , OC 3 F 6 , OC 4 F 8 , OC 5 F 10 and OC 6 F 12 , or a combination of two or three groups selected from these groups.
  • R 9 is preferably a group selected from OCF 2 , OC 2 F 4 , OC 3 F 6 and OC 4 F 8 , or a combination of two or three groups selected from these groups, and more preferably -OC 2 F 4 OC 3 F 6 -.
  • R 6 , R 7 and g have the same meanings as those described in the above formula (f3) and have the same embodiments.
  • R 6 ' , R 7 ' and g ' have the same meanings as those described in the above formula (f3) and have the same embodiments.
  • R r is preferably [In the formula, * indicates the bond position.] and more preferably [In the formula, * indicates the bond position.] It is.
  • e is preferably an integer of 1 or more and 100 or less, more preferably an integer of 5 or more and 100 or less.
  • the sum of a, b, c, d, e, and f is preferably 5 or more, more preferably 10 or more, for example, 10 or more and 100 or less.
  • f is preferably an integer of 1 or more and 100 or less, more preferably an integer of 5 or more and 100 or less.
  • the sum of a, b, c, d, e, and f is preferably 5 or more, more preferably 10 or more, for example, 10 or more and 100 or less.
  • R F is a group represented by the above formula (f1).
  • R F is a group represented by the above formula (f2).
  • R F is a group represented by the above formula (f3).
  • R F is a group represented by the above formula (f4).
  • R F is a group represented by the above formula (f5).
  • R F is a group represented by the above formula (f6).
  • the ratio of e to f (hereinafter referred to as "e/f ratio”) is 0.1 to 10, preferably 0.2 to 5, more preferably 0.2 to 2, even more preferably 0.2 to 1.5, and even more preferably 0.2 to 0.85.
  • e/f ratio 10 the slipperiness, friction durability, and chemical resistance (e.g., durability against artificial sweat) of the surface treatment layer obtained from this compound are further improved.
  • the smaller the e/f ratio the more the slipperiness and friction durability of the surface treatment layer are improved.
  • the e/f ratio 0.1 or more the stability of the compound can be further improved. The larger the e/f ratio, the more the stability of the compound is improved.
  • the e/f ratio is preferably 0.2 to 0.95, and more preferably 0.2 to 0.9.
  • the e/f ratio is preferably 1.0 or more, and more preferably 1.0 to 2.0.
  • the number average molecular weights of RF1 and RF2 are not particularly limited, but are, for example, 500 to 30,000, preferably 1,500 to 30,000, and more preferably 2,000 to 10,000.
  • the number average molecular weights of RF1 and RF2 are values measured by 19F -NMR.
  • the number average molecular weight of RF1 and RF2 may be from 500 to 30,000, preferably from 1,000 to 20,000, more preferably from 2,000 to 15,000, even more preferably from 2,000 to 10,000, for example from 3,000 to 6,000.
  • the number average molecular weight of RF1 and RF2 can be from 4,000 to 30,000, preferably from 5,000 to 10,000, and more preferably from 6,000 to 10,000.
  • Rf 1 is a C 1-16 alkyl group optionally substituted with one or more fluorine atoms.
  • the "C 1-16 alkyl group" in the above-mentioned C 1-16 alkyl group optionally substituted by one or more fluorine atoms may be a straight chain or a branched chain, and is preferably a straight chain or branched chain C 1-6 alkyl group, particularly a C 1-3 alkyl group, and more preferably a straight chain C 1-6 alkyl group, particularly a C 1-3 alkyl group.
  • Rf 1 is preferably a C 1-16 alkyl group substituted with one or more fluorine atoms, more preferably a CF 2 H—C 1-15 perfluoroalkylene group, and even more preferably a C 1-16 perfluoroalkyl group.
  • the C 1-16 perfluoroalkyl group may be linear or branched, and is preferably a linear or branched C 1-6 perfluoroalkyl group, in particular a C 1-3 perfluoroalkyl group, and more preferably a linear C 1-6 perfluoroalkyl group, in particular a C 1-3 perfluoroalkyl group, specifically -CF 3 , -CF 2 CF 3 , or CF 2 CF 2 CF 3 .
  • Rf2 is a C 1-6 alkylene group optionally substituted with one or more fluorine atoms.
  • C 1-6 alkylene group in the above-mentioned C 1-6 alkylene group optionally substituted by one or more fluorine atoms may be a straight chain or a branched chain, and is preferably a straight chain or branched chain C 1-3 alkylene group, and more preferably a straight chain C 1-3 alkylene group.
  • Rf 2 is preferably a C 1-6 alkylene group substituted with one or more fluorine atoms, more preferably a C 1-6 perfluoroalkylene group, and even more preferably a C 1-3 perfluoroalkylene group.
  • the above C 1-6 perfluoroalkylene group may be linear or branched, and is preferably a linear or branched C 1-3 perfluoroalkylene group, more preferably a linear C 1-3 perfluoroalkylene group, specifically, -CF 2 -, -CF 2 CF 2 -, or CF 2 CF 2 CF 2 -.
  • p is 0 or 1. In one embodiment, p is 0. In another embodiment, p is 1.
  • q is 0 or 1. In one embodiment, q is 0. In another embodiment, q is 1.
  • each R 1 F is independently a divalent fluoropolyether group.
  • RF is preferably the following: -(OC h1 R Fa 2h1 ) h3 -(OC h2 R Fa 2h2-2 ) h4 - [Wherein: Each R Fa is independently a hydrogen atom, a fluorine atom, or a chlorine atom; h1 is an integer from 1 to 6, h2 is an integer from 4 to 8, h3 is an integer equal to or greater than 0; h4 is an integer equal to or greater than 0; However, the number of repeating units of h3 and h4 is 1 or more, preferably 2 or more, and more preferably 5 or more, and the order of the repeating units enclosed in parentheses with h3 and h4 is arbitrary in the formula. It may contain a group represented by:
  • RF can be linear or branched.
  • RF is preferably represented by the formula: -(OC 6 F 12 ) a -(OC 5 F 10 ) b -(OC 4 F 8 ) c -(OC 3 R Fa 6 ) d -(OC 2 F 4 ) e -(OCF 2 ) f -
  • Each R Fa is independently a hydrogen atom, a fluorine atom, or a chlorine atom
  • a, b, c, d, e, and f each independently represent an integer of 0 to 200, and the sum of a, b, c, d, e, and f is 1 or more.
  • the order of the repeating units enclosed in parentheses with a, b, c, d, e, or f is arbitrary in the formula.
  • It is a group represented by the following formula:
  • R Fa is preferably a hydrogen atom or a fluorine atom, and more preferably a fluorine atom.
  • a, b, c, d, e and f may each preferably be independently an integer from 0 to 100.
  • the sum of a, b, c, d, e and f is preferably 5 or more, more preferably 10 or more, and may be, for example, 15 or more or 20 or more.
  • the sum of a, b, c, d, e and f is preferably 200 or less, more preferably 100 or less, and even more preferably 60 or less, and may be, for example, 50 or less or 30 or less.
  • repeating units may be linear or branched.
  • the repeating unit may be - ( OC6F12 ) - , -( OCF2CF2CF2CF2CF2CF2CF2CF2 ) - , - (OCF( CF3 ) CF2CF2CF2CF2CF2 )-, - ( OCF2CF ( CF3 ) CF2CF2CF2 ) - , -(OCF2CF2CF ( CF3)CF2CF2CF2)- , - ( OCF2CF2CF2CF ( CF3 ) CF2CF2 )- , - ( OCF2CF2CF2CF2CF ( CF3 ) CF2 )- , -( OCF2CF2CF2CF2CF ( CF3 ) CF2 )- , -( OCF2CF2CF2CF2CF ( CF3 ) CF2 )-, and the like .
  • -(OC 5 F 10 )- is -(OCF 2 CF 2 CF 2 CF 2 CF 2 )-, -(OCF(CF 3 )CF 2 CF 2 CF 2 )-, -(OCF 2 CF(CF 3 )CF 2 CF 2 )-, -(OCF 2 CF 2 CF (CF 3 ) CF 2 )-, -(OCF 2 CF 2 CF (CF 3 ))-, etc. may be used.
  • - ( OC4F8 )- may be any of -( OCF2CF2CF2CF2 )-, -(OCF( CF3 ) CF2CF2 ) -, - ( OCF2CF ( CF3 ) CF2 )-, - ( OCF2CF2CF ( CF3 ))-, -(OC( CF3 ) 2CF2 )-, - ( OCF2C ( CF3 ) 2 )- , -(OCF( CF3 )CF( CF3 )) - , - (OCF( C2F5 ) CF2 )- and ( OCF2CF ( C2F5 ))-.
  • -(OC 3 F 6 )- (i.e., in the above formula, R Fa is a fluorine atom) may be any of -(OCF 2 CF 2 CF 2 )-, -(OCF(CF 3 )CF 2 )-, and (OCF 2 CF(CF 3 ))-.
  • -(OC 2 F 4 )- may be any of -(OCF 2 CF 2 )- and (OCF(CF 3 ))-.
  • the repeating unit is linear. By making the repeating unit linear, the surface slip properties, friction durability, etc. of the surface treatment layer can be improved.
  • the repeating unit is branched. By making the repeating unit branched, the dynamic friction coefficient of the surface treatment layer can be increased.
  • R F can include a ring structure.
  • the ring structure may be a three-, four-, five-, or six-membered ring as shown below. [In the formula, * indicates the bond position.]
  • the ring structure may preferably be a four-membered ring, a five-membered ring, or a six-membered ring, more preferably a four-membered ring or a six-membered ring.
  • the repeating unit having a ring structure may preferably be the following unit. [In the formula, * indicates the bond position.]
  • each R F is independently a group represented by any one of the following formulas (f1) to (f6).
  • -(OC 3 F 6 ) d - (OC 2 F 4 ) e - (f1) [In the formula, d is an integer from 1 to 200, and e is 0 or 1.]
  • c and d each independently represent an integer of 0 or more and 30 or less
  • e and f each independently represent an integer of 1 or more and 200 or less, the sum of c, d, e, and f is 2 or more;
  • the order of occurrence of each repeat unit enclosed in parentheses with the subscript c, d, e, or f is arbitrary in the formula.
  • R6 is OCF2 or OC2F4
  • R7 is a group selected from OC2F4 , OC3F6 , OC4F8 , OC5F10 and OC6F12 , or a combination of two or three groups independently selected from these groups
  • g is an integer from 2 to 100
  • R6 ' is OCF2 or OC2F4
  • R 7′ is a group selected from OC 2 F 4 , OC 3 F 6 ,
  • d is preferably an integer of 5 to 200, more preferably 10 to 100, even more preferably 15 to 50, for example, an integer of 25 to 35.
  • e is 1.
  • (OC 3 F 6 ) is preferably a group represented by (OCF 2 CF 2 CF 2 ), (OCF 2 CF(CF 3 )) or (OCF(CF 3 )CF 2 ), more preferably a group represented by -(OCF 2 CF 2 CF 2 ) d -.
  • (OC 2 F 4 ) is a group represented by (OCF 2 CF 2 ) or (OCF(CF 3 )), preferably a group represented by (OCF 2 CF 2 ).
  • e and f are each independently preferably an integer of 5 or more and 200 or less, more preferably an integer of 10 to 200.
  • the sum of c, d, e and f is preferably 5 or more, more preferably 10 or more, and may be, for example, 15 or more or 20 or more.
  • the above formula (f2) is preferably a group represented by -(OCF 2 CF 2 CF 2 CF 2 ) c -(OCF 2 CF 2 CF 2 ) d -(OCF 2 CF 2 ) e -(OCF 2 ) f -.
  • the formula (f2) may be a group represented by -(OC 2 F 4 ) e -(OCF 2 ) f -.
  • R6 is preferably OC2F4 .
  • R7 is preferably a group selected from OC2F4 , OC3F6 , and OC4F8 , or a combination of two or three groups independently selected from these groups , and more preferably a group selected from OC3F6 and OC4F8 .
  • the combination of two or three groups independently selected from OC 2 F 4 , OC 3 F 6 and OC 4 F 8 is not particularly limited, and examples thereof include -OC 2 F 4 OC 3 F 6 -, -OC 2 F 4 OC 4 F 8 -, -OC 3 F 6 OC 2 F 4 -, -OC 3 F 6 OC 3 F 6 -, -OC 3 F 6 OC 4 F 8 -, -OC 4 F 8 OC 4 F 8 -, -OC 4 F 8 OC 3 F 6 -, -OC 4 F 8 OC 2 F 4 -, -OC 2 F 4 OC 2 F 4 OC 3 F 6 -, -OC 2 F 4 OC 2 F 4 OC 3 F 6 -, -OC 2 F 4 OC 2 F 4 OC 4 F 8 -, -OC 2 F 4 OC 3 F 6 -, -OC 2 F 4 OC 2 F 4 OC 4 F 8 -, -OC 2 F 4 OC 3 F 6 -,
  • g is preferably an integer of 3 or more, more preferably 5 or more.
  • the above g is preferably an integer of 50 or less.
  • OC 2 F 4 , OC 3 F 6 , OC 4 F 8 , OC 5 F 10 and OC 6 F 12 may be either linear or branched, and are preferably linear.
  • the above formula (f3) is preferably -(OC 2 F 4 -OC 3 F 6 ) g - or (OC 2 F 4 -OC 4 F 8 ) g -.
  • R 6 , R 7 and g have the same meanings as those described in the above formula (f3) and have the same embodiments.
  • R 6 ' , R 7 ' and g ' have the same meanings as those described in the above formula (f3) and have the same embodiments.
  • R r is preferably [In the formula, * indicates the bond position.] and more preferably [In the formula, * indicates the bond position.] It is.
  • e is preferably an integer of 1 or more and 100 or less, more preferably an integer of 5 or more and 100 or less.
  • the sum of a, b, c, d, e, and f is preferably 5 or more, more preferably 10 or more, for example, 10 or more and 100 or less.
  • f is preferably an integer of 1 or more and 100 or less, more preferably an integer of 5 or more and 100 or less.
  • the sum of a, b, c, d, e, and f is preferably 5 or more, more preferably 10 or more, for example, 10 or more and 100 or less.
  • the R F is a group represented by the formula (f1).
  • the RF is a group represented by the formula (f2).
  • the R F is a group represented by the formula (f3).
  • the R F is a group represented by the formula (f4).
  • the R F is a group represented by the formula (f5).
  • the R F is a group represented by the formula (f6).
  • the ratio of e to f (hereinafter referred to as "e/f ratio”) is 0.1 to 10, preferably 0.2 to 5, more preferably 0.2 to 2, even more preferably 0.2 to 1.5, and even more preferably 0.2 to 0.85.
  • e/f ratio 10 the slipperiness, friction durability, and chemical resistance (e.g., durability against artificial sweat) of the surface treatment layer obtained from this compound are further improved.
  • the smaller the e/f ratio the more the slipperiness and friction durability of the surface treatment layer are improved.
  • the e/f ratio 0.1 or more the stability of the compound can be further improved. The larger the e/f ratio, the more the stability of the compound is improved.
  • the e/f ratio is preferably 0.2 to 0.95, and more preferably 0.2 to 0.9.
  • the e/f ratio is preferably 1.0 or more, and more preferably 1.0 to 2.0.
  • the number average molecular weights of RF1 and RF2 are not particularly limited, but are, for example, 500 to 30,000, preferably 1,500 to 30,000, and more preferably 2,000 to 10,000.
  • the number average molecular weights of RF1 and RF2 are values measured by 19F -NMR.
  • the number average molecular weight of RF1 and RF2 may be from 500 to 30,000, preferably from 1,000 to 20,000, more preferably from 2,000 to 15,000, even more preferably from 2,000 to 10,000, for example from 3,000 to 6,000.
  • the number average molecular weight of RF1 and RF2 can be from 4,000 to 30,000, preferably from 5,000 to 10,000, and more preferably from 6,000 to 10,000.
  • Each X B1 independently represents a single bond or a divalent organic group.
  • X B1 is a single bond.
  • each X B1 is independently a divalent organic group.
  • X B1a is preferably --O-- or C(.dbd.O)O--, more preferably --O--.
  • XB1a is preferably represented by the following formula: -O-(CH 2 ) m11 - (In the formula, m11 is an integer of 1 to 6, preferably an integer of 1 to 3.) -(CH 2 ) m12 -O-(CH 2 ) m13 - (In the formula, m12 is an integer of 1 to 6, preferably an integer of 1 to 3, and m13 is an integer of 1 to 6, preferably an integer of 1 to 3.) It is a group represented by the following formula:
  • XB1a is not particularly limited, but specifically includes Examples include -CH2- , -C2H4- , -C3H6-, -C4H8- , -O -CH2-, -OC2H4-, -OC3H6- and the like .
  • Each R 3 C is independently a hydrogen atom or a monovalent group.
  • R 3 C is a hydrogen atom.
  • R 3 C is a monovalent group.
  • the monovalent group is preferably a halogen atom, -R 1 -R A , or a monovalent group containing a fluoropolyether group.
  • a monovalent group containing a fluoropolyether group has the same meaning as the monovalent group containing a fluoropolyether group in R B.
  • the halogen atom is a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, preferably a chlorine atom, a bromine atom, or an iodine atom, more preferably a chlorine atom or a bromine atom, and even more preferably a chlorine atom.
  • R C is —R 1 —R A.
  • R 3 C is a halogen atom, preferably a chlorine atom.
  • ⁇ is 1 or 2, preferably 1.
  • the fluorine-containing compound of the present disclosure can be synthesized, for example, as follows.
  • a compound represented by formula (f2): OCN-R 54 (O-CO-CR 3 CH 2 ) 2 (f2) [Wherein: R 54 is a trivalent organic group; R3 is a hydrogen atom or a hydrocarbon group.
  • R 54 is a trivalent organic group; R3 is a hydrogen atom or a hydrocarbon group.
  • R 61 is a divalent organic group
  • R P is a leaving group such as -O-tosyl
  • R 62 is a hydrocarbon group, for example, a C 1-6 alkyl group, preferably a methyl group.
  • a compound represented by formula (f2): OCN-R 54 (O-CO-CR 3 CH 2 ) 2 (f2)
  • R 54 is a trivalent organic group
  • R3 is a hydrogen atom or a hydrocarbon group.
  • a compound represented by formula (j) to obtain a compound represented by formula (k2):
  • R Ac is -OCO-CR 3 ⁇ CH 2 ;
  • RF1 , R3 , R51 , R52 and R54 are as defined above.
  • the surface treatment agent disclosed herein contains a fluorine-containing compound represented by formula (1).
  • the fluorine-containing compound in the surface treatment agent disclosed herein is a compound represented by formula (1) in which ⁇ is 1.
  • the fluorine-containing compound in the surface treatment agent of the present disclosure is a compound represented by formula (1) in which ⁇ is 2.
  • the fluorine-containing compound in the surface treatment agent of the present disclosure is a compound represented by formula (1) in which ⁇ is 1 and a compound represented by formula (1) in which ⁇ is 2.
  • the compound represented by formula (1) in which ⁇ is 2 is preferably 0.1 mol% or more and 35 mol% or less with respect to the total of the compound represented by formula (1) in which ⁇ is 1 and the compound represented by formula (1) in which ⁇ is 2.
  • the lower limit of the content of the compound represented by formula (1) in which ⁇ is 2 with respect to the total of the compound represented by formula (1) in which ⁇ is 1 and the compound represented by formula (1) in which ⁇ is 2 may be preferably 0.1 mol%, more preferably 0.2 mol%, even more preferably 0.5 mol%, even more preferably 1 mol%, particularly preferably 2 mol%, and especially 5 mol%.
  • the upper limit of the content of the compound represented by formula (1) in which ⁇ is 2 with respect to the total of the compound represented by formula (1) in which ⁇ is 1 and the compound represented by formula (1) in which ⁇ is 2 may be preferably 35 mol%, more preferably 30 mol%, even more preferably 20 mol%, even more preferably 15 mol% or 10 mol%.
  • the ratio of the compound represented by formula (1) in which ⁇ is 2 to the total of the compound represented by formula (1) in which ⁇ is 1 and the compound represented by formula (1) in which ⁇ is 2 is preferably 0.1 mol% to 30 mol%, more preferably 0.1 mol% to 20 mol%, even more preferably 0.2 mol% to 10 mol%, even more preferably 0.5 mol% to 10 mol%, particularly preferably 1 mol% to 10 mol%, for example, 2 mol% to 10 mol% or 5 mol% to 10 mol%.
  • the content of the compound represented by formula (1) may be preferably 0.1 to 50.0 mass%, more preferably 1.0 to 30.0 mass%, even more preferably 5.0 to 25.0 mass%, and particularly preferably 10.0 to 20.0 mass%, based on the total mass of the surface treatment agent.
  • the surface treatment agent of the present disclosure may contain a solvent, a (non-reactive) fluoropolyether compound that may be understood as a fluorine-containing oil, preferably a perfluoro(poly)ether compound (hereinafter collectively referred to as "fluorine-containing oil”), a (non-reactive) silicone compound that may be understood as a silicone oil (hereinafter referred to as "silicone oil”), alcohols, a catalyst, a surfactant, a polymerization inhibitor, a sensitizer, etc.
  • the solvent examples include aliphatic hydrocarbons such as hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, and mineral spirits; aromatic hydrocarbons such as benzene, toluene, xylene, naphthalene, and solvent naphtha; methyl acetate, ethyl acetate, propyl acetate, n-butyl acetate, isopropyl acetate, isobutyl acetate, cellosolve acetate, propylene glycol methyl ether acetate, carbitol acetate, diethyl oxalate, ethyl pyruvate, ethyl 2-hydroxybutyrate, ethyl acetoacetate, amyl acetate, methyl lactate, ethyl lactate, 3-methoxyphenyl ether acetate, methyl
  • Esters such as methyl cypropionate, ethyl 3-methoxypropionate, methyl 2-hydroxyisobutyrate, and ethyl 2-hydroxyisobutyrate; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, 2-hexanone, cyclohexanone, methyl amino ketone, and 2-heptanone; ethyl cellosolve, methyl cellosolve, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, propylene glycol glycol ethers such as propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, dipropylene glycol dimethyl ether, and ethylene glyco
  • ethers such as N,N-dimethylformamide and N,N-dimethylacetamide
  • ether alcohols such as methyl cellosolve, cellosolve, isopropyl cellosolve, butyl cellosolve, and diethylene glycol monomethyl ether; diethylene glycol monoethyl ether acetate
  • fluorine-containing solvents such as 1,1,2-trichloro-1,2,2-trifluoroethane, 1,2-dichloro-1,1,2,2-tetrafluoroethane, dimethyl sulfoxide, 1,1-dichloro-1,2,2,3,3-pentafluoropropane (HCFC225), Zeorora H, HFE7100, HFE7200, HFE7300, CF 3 CH 2 OH, CF 3 CF 2 CH 2 OH, and (CF 3 ) 2 CHOH.
  • a mixed solvent of two or more of these may be used.
  • the fluorine-containing oil is not particularly limited, but examples thereof include compounds represented by the following general formula (3) (perfluoro(poly)ether compounds).
  • Rf 5 represents an alkyl group having 1 to 16 carbon atoms (preferably a C 1-16 perfluoroalkyl group) which may be substituted by one or more fluorine atoms
  • Rf 6 represents an alkyl group having 1 to 16 carbon atoms (preferably a C 1-16 perfluoroalkyl group) which may be substituted by one or more fluorine atoms, a fluorine atom or a hydrogen atom
  • Rf 5 and Rf 6 are more preferably each independently a C 1-3 perfluoroalkyl group.
  • a', b', c' and d' respectively represent the number of four types of repeating units of the perfluoro(poly)ether constituting the main skeleton of the polymer, and are each independently an integer of 0 to 300, and the sum of a', b', c' and d' is at least 1, preferably 1 to 300, and more preferably 20 to 300.
  • the order of occurrence of each repeating unit enclosed in parentheses with the subscript a', b', c' or d' is arbitrary in the formula.
  • -(OC 4 F 8 )- may be any of -(OCF 2 CF 2 CF 2 CF 2 )-, -(OCF(CF 3 )CF 2 CF 2 )-, -(OCF 2 CF(CF 3 )CF 2 )-, -(OCF 2 CF 2 CF(CF 3 ))-, -(OCF 2 C(CF 3 ) 2 )-, -(OCF(CF 3 )CF(CF 3 ))-, -(OCF(C 2 F 5 )CF 2 )- and (OCF 2 CF(C 2 F 5 ))-, preferably -(OCF 2 -(OC 3 F 6 )- may be any of -(OCF 2 CF 2 CF 2 )-, -(OCF(CF 3 )CF 2 ) - , and (OCF 2 CF(CF 3 ))-,
  • Examples of the perfluoro(poly)ether compound represented by the above general formula (3) include compounds represented by the following general formulas (3a) and (3b) (which may be one type or a mixture of two or more types): Rf 5 - (OCF 2 CF 2 CF 2 ) b" - Rf 6 ... (3a) Rf 5 - (OCF 2 CF 2 CF 2 ) a" - (OCF 2 CF 2 CF 2 ) b" - (OCF 2 CF 2 ) c" - (OCF 2 ) d" - Rf 6 ...
  • Rf5 and Rf6 are as defined above; in formula (3a), b" is an integer of 1 or more and 100 or less; in formula (3b), a" and b" are each independently an integer of 0 or more and 30 or less, and c" and d" are each independently an integer of 1 or more and 300 or less.
  • the order of occurrence of each repeating unit enclosed in parentheses with the subscripts a", b", c", and d" is arbitrary in the formula.
  • the fluorine-containing oil may be a compound represented by the general formula Rf 3 -F (wherein Rf 3 is a C 5-16 perfluoroalkyl group), or may be a chlorotrifluoroethylene oligomer.
  • the fluorine-containing oil may have an average molecular weight of 500 to 10,000.
  • the molecular weight of the fluorine-containing oil can be measured using GPC.
  • the fluorine-containing oil may be contained in an amount of, for example, 0 to 50 mass%, preferably 0 to 30 mass%, and more preferably 0 to 5 mass% relative to the surface treatment agent of the present disclosure.
  • the surface treatment agent of the present disclosure is substantially free of fluorine-containing oil. "Substantially free of fluorine-containing oil” means that the surface treatment agent does not contain any fluorine-containing oil at all, or may contain a very small amount of fluorine-containing oil.
  • the average molecular weight of the fluorine-containing oil may be greater than the average molecular weight of the fluorine-containing compound.
  • the average molecular weight of the fluorine-containing oil may be smaller than the average molecular weight of the fluorine-containing compound.
  • the fluorinated oil contributes to improving the surface slipperiness of the layer formed by the surface treatment agent of the present disclosure.
  • the silicone oil for example, a linear or cyclic silicone oil having 2,000 or less siloxane bonds can be used.
  • the linear silicone oil may be so-called straight silicone oil or modified silicone oil.
  • straight silicone oil include dimethyl silicone oil, methylphenyl silicone oil, and methylhydrogen silicone oil.
  • modified silicone oil include straight silicone oil modified with alkyl, aralkyl, polyether, higher fatty acid ester, fluoroalkyl, amino, epoxy, carboxyl, alcohol, etc.
  • Examples of cyclic silicone oil include cyclic dimethylsiloxane oil, etc.
  • such silicone oil can be contained in an amount of, for example, 0 to 300 parts by mass, preferably 50 to 200 parts by mass, per 100 parts by mass of the total of the fluorine-containing compounds of the present disclosure (if there are two or more types, the total of these, the same applies below).
  • Silicone oil helps improve the surface slipperiness of the surface treatment layer.
  • Examples of the alcohols include alcohols having 1 to 6 carbon atoms which may be substituted with one or more fluorine atoms, such as methanol , ethanol, isopropanol, tert-butanol , CF3CH2OH , CF3CF2CH2OH , and ( CF3 ) 2CHOH . Addition of these alcohols to the surface treatment agent improves the stability of the surface treatment agent and also improves the compatibility of the perfluorinated compound with the solvent.
  • fluorine atoms such as methanol , ethanol, isopropanol, tert-butanol , CF3CH2OH , CF3CF2CH2OH , and ( CF3 ) 2CHOH .
  • the alcohol is preferably 2,2,3,3,3-pentafluoro-1-propanol or 2,2,2-trifluoroethanol.
  • the catalyst may be an acid (e.g., acetic acid, trifluoroacetic acid, etc.), a base (e.g., ammonia, triethylamine, diethylamine, etc.), or a transition metal (e.g., Ti, Ni, Sn, etc.).
  • an acid e.g., acetic acid, trifluoroacetic acid, etc.
  • a base e.g., ammonia, triethylamine, diethylamine, etc.
  • a transition metal e.g., Ti, Ni, Sn, etc.
  • the catalyst promotes the hydrolysis and dehydration condensation of the fluorine-containing compound of the present disclosure, and promotes the formation of the layer formed by the surface treatment agent of the present disclosure.
  • the surface treatment agent of the present disclosure can be impregnated into a porous material, such as a porous ceramic material, or a metal fiber, such as steel wool, and formed into pellets.
  • a porous material such as a porous ceramic material, or a metal fiber, such as steel wool
  • the pellets can be used, for example, in vacuum deposition.
  • the surface treatment agent disclosed herein may contain trace amounts of impurities such as Pt, Rh, Ru, 1,3-divinyltetramethyldisiloxane, triphenylphosphine, NaCl, KCl, and silane condensates.
  • impurities such as Pt, Rh, Ru, 1,3-divinyltetramethyldisiloxane, triphenylphosphine, NaCl, KCl, and silane condensates.
  • the article of the present disclosure includes a substrate and a layer (surface treatment layer) formed on the substrate surface using the surface treatment agent of the present disclosure.
  • Substrates that can be used in the present disclosure may be composed of any suitable material, such as glass, resin (which may be a natural or synthetic resin, such as a common plastic material), metal, ceramics, semiconductors (silicon, germanium, etc.), fibers (woven fabrics, nonwoven fabrics, etc.), fur, leather, wood, ceramics, stone, etc., building materials, sanitary products, etc.
  • resin which may be a natural or synthetic resin, such as a common plastic material
  • metal ceramics, semiconductors (silicon, germanium, etc.), fibers (woven fabrics, nonwoven fabrics, etc.), fur, leather, wood, ceramics, stone, etc., building materials, sanitary products, etc.
  • the material constituting the surface of the substrate may be a material for optical members, such as glass or transparent plastic.
  • some layer (or film), such as a hard coat layer or an anti-reflection layer may be formed on the surface (outermost layer) of the substrate.
  • the anti-reflection layer may be either a single-layer anti-reflection layer or a multi-layer anti-reflection layer.
  • Examples of inorganic substances that can be used for the anti-reflection layer include SiO 2 , SiO, ZrO 2 , TiO 2 , TiO, Ti 2 O 3 , Ti 2 O 5 , Al 2 O 3 , Ta 2 O 5 , Ta 3 O 5 , Nb 2 O 5 , HfO 2 , Si 3 N 4 , CeO 2 , MgO, Y 2 O 3 , SnO 2 , MgF 2 , WO 3 and the like. These inorganic substances may be used alone or in combination of two or more of them (for example, as a mixture). When a multi-layer antireflection layer is used, it is preferable to use SiO 2 and/or SiO 2 for the outermost layer.
  • a transparent electrode for example, a thin film using indium tin oxide (ITO) or indium zinc oxide, may be provided on a part of the surface of the substrate (glass).
  • the substrate may have an insulating layer, an adhesive layer, a protective layer, a decorative frame layer (I-CON), an atomizing film layer, a hard coating film layer, a polarizing film, a phase difference film, and a liquid crystal display module, depending on the specific specifications.
  • the shape of the substrate is not particularly limited and may be, for example, a plate, a film, or other shape.
  • the surface region of the substrate on which the surface treatment layer is to be formed may be at least a part of the substrate surface, and may be appropriately determined depending on the application and specific specifications of the product to be manufactured.
  • At least the surface portion of the substrate may be made of a material that originally has hydroxyl groups.
  • materials include glass, metals (particularly base metals), ceramics, semiconductors, etc., on whose surfaces natural oxide films or thermal oxide films are formed.
  • the substrate may be subjected to some pretreatment to introduce or increase the number of hydroxyl groups on the substrate surface. Examples of such pretreatment include plasma treatment (e.g., corona discharge) and ion beam irradiation.
  • Plasma treatment can introduce or increase hydroxyl groups on the substrate surface, and can also be suitably used to clean the substrate surface (remove foreign matter, etc.).
  • Another example of such pretreatment is a method in which an interfacial adsorbent having carbon-carbon unsaturated bond groups is formed in advance in the form of a monomolecular film on the substrate surface by the LB method (Langmuir-Blodgett method) or chemical adsorption method, and then the unsaturated bonds are cleaved in an atmosphere containing oxygen, nitrogen, etc.
  • At least the surface portion of such a substrate may be made of a material containing another reactive group, such as a silicone compound having one or more Si-H groups, or an alkoxysilane.
  • the substrate is glass.
  • glass examples include sapphire glass, soda-lime glass, alkali aluminosilicate glass, borosilicate glass, alkali-free glass, crystal glass, and quartz glass, and particularly preferred are chemically strengthened soda-lime glass, chemically strengthened alkali aluminosilicate glass, and chemically bonded borosilicate glass.
  • the article of the present disclosure can be produced by forming a layer of the surface treatment agent of the present disclosure on the surface of the substrate, and then post-treating this layer as necessary, thereby forming a layer from the surface treatment agent of the present disclosure.
  • the formation of a layer of the surface treatment agent of the present disclosure can be carried out by applying the surface treatment agent to the surface of the substrate so as to coat the surface.
  • the coating method is not particularly limited. For example, a wet coating method and a dry coating method can be used.
  • wet coating methods include dip coating, spin coating, flow coating, spray coating, roll coating, gravure coating, and similar methods.
  • dry coating methods include deposition (usually vacuum deposition), sputtering, CVD, and similar methods.
  • deposition methods usually vacuum deposition
  • deposition methods include resistance heating, electron beam, high frequency heating such as using microwaves, ion beam, and similar methods.
  • CVD methods include plasma-CVD, optical CVD, thermal CVD, and similar methods.
  • the surface treatment agent of the present disclosure may be diluted with a solvent and then applied to the substrate surface.
  • the following solvents are preferably used: perfluoroaliphatic hydrocarbons having 5 to 12 carbon atoms (e.g., perfluorohexane, perfluoromethylcyclohexane, and perfluoro-1,3-dimethylcyclohexane); polyfluoroaromatic hydrocarbons (e.g., bis(trifluoromethyl)benzene); polyfluoroaliphatic hydrocarbons (e.g., C 6 F 13 CH 2 CH 3 (e.g., Asahiklin (registered trademark) AC-6000 manufactured by Asahi Glass Co., Ltd.), 1,1,2,2,3,3,4-heptafluorocyclopentane (e.g., Zeorora (registered trademark) H manufactured by Zeon Corporation); hydrofluoro
  • alkyl perfluoroalkyl ethers perfluoroalkyl groups and alkyl groups may be linear or branched), or CF 3 CH 2 OCF 2 CHF 2 (e.g., Asahiklin (registered trademark) AE-3000 manufactured by Asahi Glass Co., Ltd.).
  • solvents can be used alone or as a mixture of two or more kinds.
  • hydrofluoroethers are preferred, and perfluorobutyl methyl ether (C 4 F 9 OCH 3 ) and/or perfluorobutyl ethyl ether (C 4 F 9 OC 2 H 5 ) are particularly preferred.
  • the surface treatment agent of the present disclosure may be subjected to the dry coating method as is, or may be diluted with the above-mentioned solvent and then subjected to the dry coating method.
  • the layer of the surface treatment agent is preferably formed so that the surface treatment agent of the present disclosure is present in the layer together with a catalyst for hydrolysis and dehydration condensation.
  • the surface treatment agent of the present disclosure may be diluted with a solvent, and then a catalyst may be added to the diluted solution of the surface treatment agent of the present disclosure immediately before application to the substrate surface.
  • the surface treatment agent of the present disclosure to which a catalyst has been added may be directly subjected to deposition (usually vacuum deposition) treatment, or a pellet-shaped material in which the surface treatment agent of the present disclosure to which a catalyst has been added is impregnated onto a metal porous body such as iron or copper may be used to perform deposition (usually vacuum deposition) treatment.
  • Any suitable acid or base can be used as the catalyst.
  • acid catalysts that can be used include acetic acid, formic acid, and trifluoroacetic acid.
  • base catalysts that can be used include ammonia and organic amines.
  • the surface treatment layer included in the article of the present disclosure has both high abrasion resistance and low wear resistance.
  • the surface treatment layer may also have water repellency, oil repellency, stain resistance (preventing adhesion of stains such as fingerprints), waterproofing (preventing water from penetrating into electronic components, etc.), surface slipperiness (or lubricity, e.g. ease of wiping off stains such as fingerprints and excellent tactile feel against the fingers), chemical resistance, etc., and may be suitably used as a functional thin film.
  • the present disclosure also relates to an optical material having the above-mentioned surface treatment layer as the outermost layer.
  • optical materials in addition to optical materials related to displays such as those exemplified below, a wide variety of optical materials are preferably used: for example, displays such as cathode ray tubes (CRTs; e.g., personal computer monitors), liquid crystal displays, plasma displays, organic electroluminescent displays, inorganic thin-film electroluminescent dot matrix displays, rear projection displays, fluorescent display tubes (VFDs), field emission displays (FEDs; Field Emission Displays), or protective plates for such displays, or displays with anti-reflection coating applied to their surfaces.
  • CTRs cathode ray tubes
  • LCDs organic electroluminescent displays
  • inorganic thin-film electroluminescent dot matrix displays rear projection displays
  • fluorescent display tubes (VFDs) fluorescent display tubes
  • FEDs Field Emission Displays
  • protective plates for such displays, or displays with anti-reflection coating applied to their surfaces.
  • the article of the present disclosure may be, but is not limited to, an optical component.
  • optical components include the following: lenses for glasses and the like; front protection plates, anti-reflection plates, polarizing plates, and anti-glare plates for displays such as PDPs and LCDs; touch panel sheets for devices such as mobile phones and personal digital assistants; disc surfaces of optical discs such as Blu-ray (registered trademark) discs, DVD discs, CD-Rs, and MOs; optical fibers; the display surfaces of watches, etc.
  • the article of the present disclosure may also be a medical device or medical material.
  • the article having a layer obtained by the present disclosure may also be an automobile interior or exterior component.
  • exterior materials include the following: windows, light covers, and exterior camera covers.
  • interior materials include the following: instrument panel covers, navigation system touch panels, and decorative interior materials.
  • the thickness of the layer is not particularly limited. In the case of optical components, the thickness of the layer is preferably in the range of 1 to 50 nm, preferably 1 to 30 nm, and more preferably 1 to 15 nm, from the viewpoints of optical performance, abrasion resistance, and antifouling properties.
  • Synthesis Example 3 Synthesis of (B-2) The procedure of Synthesis Example 2 was repeated except that mercaptooctanol was used instead of mercaptononanol, to obtain 51.0 g of a reaction product (B-2) of a perfluoropolyether-containing alcohol, trichlorotriazine, and mercaptooctanol.
  • Synthesis Example 4 Synthesis of (B-3) The same procedure as in Synthesis Example 2 was repeated except that mercaptohexanol was used instead of mercaptononanol, to obtain 51.2 g of a reaction product (B-3) of a perfluoropolyether-containing alcohol, trichlorotriazine, and mercaptohexanol.
  • Synthesis Example 5 Synthesis of (C-1) The same procedure as in Synthesis Example 1 was repeated except that mercaptononanol in Synthesis Example 1 was changed to diethanolamine, to obtain 50.4 g of a reaction product (C-1) of a perfluoropolyether-containing alcohol, trichlorotriazine, and diethanolamine.
  • Synthesis Example 8 Synthesis of (TA-1b) A fluoropolyether group-containing compound (TA-1b) was recovered in the same manner as in Synthesis Example 7, except that 2-acryloyloxyethyl isocyanate in Synthesis Example 7 was changed to 1,1-(bisacryloyloxymethyl)ethyl isocyanate.
  • Synthesis Example 9 Synthesis of (TB-1b) A fluoropolyether group-containing compound (TB-1b) was recovered in the same manner as in Synthesis Example 8, except that (A-1) in Synthesis Example 8 was changed to (B-1) and 2-acryloyloxyethyl isocyanate was changed to 1,1-(bisacryloyloxymethyl)ethyl isocyanate.
  • Synthesis Example 10 Synthesis of (TB-2b) A fluoropolyether group-containing compound (TB-2b) was recovered in the same manner as in Synthesis Example 9, except that (B-1) in Synthesis Example 9 was changed to (B-2).
  • Synthesis Example 11 Synthesis of (TB-2a) A fluoropolyether group-containing compound (TB-2a) was recovered in the same manner as in Synthesis Example 10, except that 1,1-(bisacryloyloxymethyl)ethyl isocyanate in Synthesis Example 10 was changed to 2-acryloyloxyethyl isocyanate.
  • Synthesis Example 12 Synthesis of (TB-3b) A fluoropolyether group-containing compound (TB-3b) was recovered in the same manner as in Synthesis Example 10, except that (B-2) in Synthesis Example 10 was changed to (B-3).
  • Synthesis Example 14 Synthesis of (TC-1b) A fluoropolyether group-containing compound (TC-1b) was recovered in the same manner as in Synthesis Example 13, except that 2-acryloyloxyethyl isocyanate in Synthesis Example 13 was changed to 1,1-(bisacryloyloxymethyl)ethyl isocyanate.
  • Synthesis Example 15 Synthesis of (TD-1a) A fluoropolyether group-containing compound (TD-1a) was recovered in the same manner as in Synthesis Example 11, except that (B-2) in Synthesis Example 11 was changed to (D-1).
  • Synthesis Example 16 Synthesis of (TD-1b) A fluoropolyether group-containing compound (TD-1b) was recovered in the same manner as in Synthesis Example 15, except that 2-acryloyloxyethyl isocyanate in Synthesis Example 15 was changed to 1,1-(bisacryloyloxymethyl)ethyl isocyanate.
  • Example BEAMSET 575CB (manufactured by Arakawa Chemical Industries, Ltd.) (1.5 g) and methyl isobutyl ketone (1.5 g) were mixed, and fluoropolyether group-containing compounds TA-1a, TA-1b, TB-1b, TB-2a, TB-2b and TB-3b were added so that each was 0.5 mass % relative to the BEAMSET 575CB, and the mixture was stirred in a rotary mixer under light shielding for 1 hour to obtain fluoropolyether-containing hard coat materials 1 to 6 (Examples 1 to 6).
  • Comparative Example 1 Fluoropolyether-containing hard coat material 7 (Comparative Example 1) was obtained in the same manner as in the above-mentioned Example, except that the fluoropolyether group-containing compound was changed to TD-1b.
  • the hard coat materials 1 to 7 (1.0 ml) obtained above were placed on a PET film (Cosmoshine A4100, manufactured by Toyobo Co., Ltd.) cut to 1/4 the size of A4 size, and a uniform coating film was formed using a bar coater.
  • the obtained coating film was irradiated with light containing 365 nm UV light at an intensity of 600 mJ/ cm2 under a nitrogen atmosphere to cure each hard coat material and obtain a cured film (surface treatment layer). The initial properties of these cured films were measured.
  • Step wool (SW) friction durability evaluation For each of the cured films in Examples 1 to 6, which had good appearances, steel wool friction durability evaluation was performed. Specifically, the substrate on which the surface treatment layer was formed was placed horizontally, and steel wool (number #0000, dimensions 5 mm x 10 mm x 10 mm) was brought into contact with the surface treatment layer of the substrate, and a load of 1,000 gf was applied thereon, and then the steel wool was reciprocated at a speed of 53.3 mm/sec (friction speed 40 rpm) while the load was applied. The static contact angle (degrees) of water was measured every 1,000 reciprocations, and the evaluation was stopped when the measured value of the contact angle became less than 100 degrees. The number of reciprocations when the contact angle finally exceeded 100 degrees is shown in Table 3.
  • Examples 1 to 6 which had good appearance, were evaluated for friction durability by the eraser friction durability test.
  • an eraser manufactured by Minoan, hardness 81 (Durometer A type), circular with a planar dimension of 0.6 cm diameter
  • the eraser was reciprocated at a speed of 48 mm/sec (friction speed 40 rpm) while the load was applied.
  • the static contact angle (degrees) of water was measured every 1000 reciprocations. The evaluation was stopped when the measured value of the contact angle became less than 100 degrees. The number of reciprocations when the contact angle finally exceeded 100 degrees is shown in Table 3.
  • This disclosure can be suitably used to form a surface treatment layer on the surface of a wide variety of substrates.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • General Physics & Mathematics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Combustion & Propulsion (AREA)
  • Nonlinear Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Mathematical Physics (AREA)
  • Polyethers (AREA)
  • Liquid Crystal (AREA)
  • Surface Treatment Of Optical Elements (AREA)
  • Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un composé contenant du fluor représenté par la formule (1). Dans la formule : R1 est -O-, -S-, ou -O-P (=O) (OR2)-, R2 sont chacun indépendamment un groupe hydrocarboné, RA sont chacun indépendamment un groupe contenant -OCO-CR3 = CH2, R3 sont chacun indépendamment un atome d'hydrogène ou un groupe hydrocarboné, RB est un groupe monovalent ou divalent contenant un groupe fluoropolyéther, RC sont chacun indépendamment un atome d'hydrogène ou un groupe monovalent, et α est 1 ou 2.
PCT/JP2024/024633 2023-07-11 2024-07-08 Composé contenant un groupe fluoropolyéther Pending WO2025013831A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR1020267000071A KR20260018148A (ko) 2023-07-11 2024-07-08 플루오로폴리에테르기 함유 화합물
CN202480046133.4A CN121464168A (zh) 2023-07-11 2024-07-08 含氟代聚醚基的化合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2023-113954 2023-07-11
JP2023113954 2023-07-11

Publications (1)

Publication Number Publication Date
WO2025013831A1 true WO2025013831A1 (fr) 2025-01-16

Family

ID=94215736

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2024/024633 Pending WO2025013831A1 (fr) 2023-07-11 2024-07-08 Composé contenant un groupe fluoropolyéther

Country Status (4)

Country Link
JP (1) JP7678388B2 (fr)
KR (1) KR20260018148A (fr)
CN (1) CN121464168A (fr)
WO (1) WO2025013831A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005517081A (ja) * 2002-02-04 2005-06-09 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー ハロゲン化光学ポリマー組成物
JP2015160902A (ja) * 2014-02-27 2015-09-07 デクセリアルズ株式会社 表面調整剤及びそれを用いた物品
WO2021024964A1 (fr) * 2019-08-02 2021-02-11 ダイキン工業株式会社 Composé isocyanul contenant du fluor

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6297358B2 (ja) 2014-02-26 2018-03-20 アマノ株式会社 白金ナノ粒子分散液、白金ナノ粒子担持フィルタ、白金ナノ粒子担持フィルタの製造方法、および空気清浄機

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005517081A (ja) * 2002-02-04 2005-06-09 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー ハロゲン化光学ポリマー組成物
JP2015160902A (ja) * 2014-02-27 2015-09-07 デクセリアルズ株式会社 表面調整剤及びそれを用いた物品
WO2021024964A1 (fr) * 2019-08-02 2021-02-11 ダイキン工業株式会社 Composé isocyanul contenant du fluor

Also Published As

Publication number Publication date
JP2025013245A (ja) 2025-01-24
JP7678388B2 (ja) 2025-05-16
CN121464168A (zh) 2026-02-03
KR20260018148A (ko) 2026-02-06

Similar Documents

Publication Publication Date Title
EP3950777B1 (fr) Composé comprenant un groupe fluoro polyether
WO2023074410A1 (fr) Agent de traitement de surface
US20220017694A1 (en) Fluoropolyether group containing compound
EP4177053A1 (fr) Composition durcissable
US12516200B2 (en) Surface treatment agent
KR102902179B1 (ko) 표면 처리제
EP4328256B1 (fr) Agent de traitement de surface
JP7678388B2 (ja) フルオロポリエーテル基含有化合物
CN119095898A (zh) 含氟代聚醚基的氧亚烷基酰胺化合物
JP7719406B2 (ja) フルオロポリエーテル基含有化合物
JP7495649B2 (ja) 表面処理剤
JP2025133086A (ja) フルオロポリエーテル基含有トリアジン化合物の組成物
WO2024237311A1 (fr) Agent de traitement de surface
JP2024166162A (ja) フルオロポリエーテル基含有化合物
JP2025167349A (ja) フッ素原子含有シラン化合物
JP2026016788A (ja) 表面処理剤

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 24839721

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 1020267000071

Country of ref document: KR

Free format text: ST27 STATUS EVENT CODE: A-0-1-A10-A15-NAP-PA0105 (AS PROVIDED BY THE NATIONAL OFFICE)

WWE Wipo information: entry into national phase

Ref document number: 1020267000071

Country of ref document: KR

WWP Wipo information: published in national office

Ref document number: 1020267000071

Country of ref document: KR

NENP Non-entry into the national phase

Ref country code: DE