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WO2025070362A1 - Composé, composition, agent de traitement de surface, article et procédé de production d'article - Google Patents

Composé, composition, agent de traitement de surface, article et procédé de production d'article Download PDF

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Publication number
WO2025070362A1
WO2025070362A1 PCT/JP2024/033866 JP2024033866W WO2025070362A1 WO 2025070362 A1 WO2025070362 A1 WO 2025070362A1 JP 2024033866 W JP2024033866 W JP 2024033866W WO 2025070362 A1 WO2025070362 A1 WO 2025070362A1
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group
compound
carbon atoms
surface treatment
integer
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Japanese (ja)
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洋介 竹田
弘毅 渡邉
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AGC Inc
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Asahi Glass Co Ltd
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    • 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
    • C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
    • 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
    • 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

Definitions

  • the present disclosure relates to compounds, compositions, surface treatment agents, articles, and methods for manufacturing articles.
  • Fluorine-containing ether compounds which contain fluorine atoms, have excellent properties such as low refractive index, low dielectric constant, water and oil repellency, heat resistance, chemical resistance, chemical stability, and transparency, and are used in a wide variety of fields such as electrical and electronic materials, semiconductor materials, optical materials, and surface treatment agents.
  • Patent Document 1 discloses that surface treatment is performed using a surface treatment agent that contains a silane compound containing a perfluoropolyether group.
  • Patent Document 2 discloses that surface treatment is performed using a surface treatment agent that contains a fluorine-containing silane compound and a metal compound that contains a transition metal such as tantalum (Ta).
  • This disclosure has been made in light of these circumstances, and aims to provide new compounds and the like capable of forming a surface treatment layer with excellent abrasion resistance.
  • the present disclosure includes the following aspects.
  • the following group P A compound comprising a fluoropolyether chain.
  • Group P -[Si(R 1 ) 2 -X] n1 -Si(R 1 ) 3 however, Each X is independently an oxygen atom or a carbon atom;
  • Each R 1 independently represents a hydrolyzable group, a group having a hydrolyzable group, a hydroxyl group, or a hydrocarbon group; At least four of R 1 are a hydrolyzable group , a group having a hydrolyzable group, or a hydroxyl group;
  • n1 is an integer from 1 to 3.
  • R f11 is a fluoroalkyl group having 1 to 20 carbon atoms, and when there are multiple R f11 , the multiple R f11 may be the same or different from each other, R f12 is a fluoroalkylene group having 1 to 6 carbon atoms, and when there are multiple R f12 , the multiple R f12 may be the same or different from each other, m1 is an integer from 0 to 500.
  • R f21 is a fluoroalkylene group having 1 to 6 carbon atoms
  • R f22 is a fluoroalkylene group having 1 to 6 carbon atoms
  • m2 is an integer from 0 to 500.
  • a composition comprising the compound according to any one of the above [1] to [8] and a liquid medium.
  • a surface treatment agent comprising the compound according to any one of the above [1] to [8].
  • a surface treatment agent comprising the compound according to any one of the above [1] to [8] and a liquid medium.
  • a method for producing an article comprising: performing a surface treatment on a substrate using a surface treatment agent containing the compound according to any one of the items [1] to [8]; and producing an article having a surface treatment layer formed on the substrate.
  • the numerical range indicated using “to” includes the numerical values before and after “to” as the minimum and maximum values, respectively.
  • the upper or lower limit of one numerical range may be replaced with the upper or lower limit of another numerical range.
  • the upper or lower limit of the numerical range may be replaced with a value shown in the examples.
  • the term “surface treatment layer” refers to a layer formed on the surface of a substrate by surface treatment.
  • Me may refer to a methyl group.
  • the "molecular weight" of a fluoropolyether chain is a number average molecular weight calculated by 1 H-NMR and 19 F-NMR to determine the number (average value) of oxyfluoroalkylene units based on the end groups.
  • the compound according to the present disclosure is a compound that includes the following group P and a fluoropolyether chain: Group P: -[Si(R 1 ) 2 -X] n1 -Si(R 1 ) 3 wherein each X is independently an oxygen atom or a carbon atom; each R 1 is independently a hydrolyzable group, a group having a hydrolyzable group, a hydroxyl group, or a hydrocarbon group; at least four of the R 1s are a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group; and n1 is an integer from 1 to 3.
  • the multiple groups P may be the same or different from each other. From the viewpoint of availability of raw materials and ease of production of the compound, it is preferable that the multiple groups P are the same.
  • Each R 1 is independently a hydrolyzable group, a group having a hydrolyzable group, a hydroxyl group, or a hydrocarbon group.
  • a hydrolyzable group is a group that becomes a hydroxyl group through a hydrolysis reaction. That is, a hydrolyzable silyl group represented by Si- R1 becomes a silanol group represented by Si-OH through a hydrolysis reaction. The silanol groups further react with each other to form a Si-O-Si bond. In addition, the silanol groups can undergo a dehydration condensation reaction with silanol groups derived from oxides present on the surface of the substrate to form a Si-O-Si bond.
  • Each X is independently an oxygen atom or a carbon atom.
  • the carbon atom in X means that Si is linked to another via one carbon atom, that is, a divalent carbon atom, and X may be -CH 2 -, -C(CH 3 ) 2 -, etc.
  • X is preferably an oxygen atom, -CH 2 -, or -C(CH 3 ) 2 -, more preferably an oxygen atom or -CH 2 -, and further preferably an oxygen atom.
  • each R 2 is independently a hydrocarbon group.
  • the hydrocarbon group include an alkyl group, a cycloalkyl group, an alkenyl group, and an allyl group, and from the viewpoint of ease of synthesis, a saturated hydrocarbon group is preferred, and an alkyl group is more preferred.
  • the number of carbon atoms in R 2 is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2.
  • group P examples include -Si(OCH 3 ) 2 -O-Si(OCH 3 ) 3 , -Si(OCH 3 ) 2 -CH 2 -Si(OCH 3 ) 3 , -Si(OCH 3 ) 2 -C(CH 3 ) 2 -Si(OCH 3 ) 3 , -Si(OCH 2 CH 3 ) 2 -O-Si(OCH 3 ) 3 , -Si(OCH 3 ) 2 -O-Si(OCH 2 CH 3 ) 3 , -Si(OCH 2 CH 3 ) 2 -O-Si(OCH 2 CH 3 ) 3 , -Si(OCH 2 CH 3 ) 2 -O-Si(OCH 2 CH 3 ) 3 , -Si(OCH 2 CH 3 ) 2 -CH 2 -Si(OCH 3 ) 3 , -Si(OCH 3 ) 2 -CH 2 -
  • the compound of the present disclosure can form a surface treatment layer having excellent abrasion resistance by having a fluoropolyether chain.
  • fluoropolyether chain examples include those similar to R f1 or R f2 described below.
  • the compound according to the present disclosure is a compound represented by the following formula (1) or the following formula (2).
  • each J 1 is independently the above-mentioned group P, and the repeated explanation is omitted.
  • R f1 is a monovalent fluoropolyether chain
  • R f2 is a divalent fluoropolyether chain
  • Q 1 and Q 2 are each independently a (1+n2)-valent linking group
  • n2 is an integer of 1 or more.
  • the monovalent fluoropolyether chain R f1 and the divalent fluoropolyether chain R f2 are groups having two or more oxyfluoroalkylene units.
  • R f1 and R f2 may each have a hydrogen atom, but the carbon atom at the terminal of Q 1 or Q 2 has a fluorine atom.
  • the molecular weight of each fluoropolyether chain is preferably 2,000 to 20,000, more preferably 2,500 to 15,000, and even more preferably 3,000 to 10,000, from the viewpoint of excellent abrasion resistance. If the molecular weight of the fluoropolyether chain is 20,000 or less, a surface treatment layer with excellent abrasion resistance can be obtained.
  • R f1 is preferably the following structure (A1). R f11 - (OR f12 ) m1 -...(A1) provided that R f11 is a fluoroalkyl group having 1 to 20 carbon atoms, and when there are multiple R f11 , the multiple R f11 may be the same or different from each other, R f12 is a fluoroalkylene group having 1 to 6 carbon atoms, and when there are multiple R f12 , the multiple R f12 may be the same or different from each other, m1 is an integer of 0 to 500. m1 is preferably an integer of 1 to 500, more preferably an integer of 2 to 500, still more preferably an integer of 10 to 200, and particularly preferably an integer of 10 to 100.
  • the divalent fluoropolyether chain R f2 is preferably the following structure (A2). -R f21 -(OR f22 ) m2 -...(A2)
  • R f21 is a fluoroalkylene group having 1 to 6 carbon atoms.
  • R f22 is a fluoroalkylene group having 1 to 6 carbon atoms, and when there are a plurality of R f22 , the plurality of R f22 may be the same or different, m2 is an integer from 0 to 500.
  • (OR f12 ) and (OR f22 ) preferably have the following structure (f2). - [(OG f1 ) m11 (OG f2 ) m12 (OG f3 ) m13 (OG f4 ) m14 (OG f5 ) m15 (OG f6 ) m16 ] - ...
  • G f1 is a fluoroalkylene group having 1 carbon atom
  • G f2 is a fluoroalkylene group having 2 carbon atoms
  • G f3 is a fluoroalkylene group having 3 carbon atoms
  • G f4 is a fluoroalkylene group having 4 carbon atoms
  • G f5 is a fluoroalkylene group having 5 carbon atoms
  • G f6 is a fluoroalkylene group having 6 carbon atoms
  • m11, m12, m13, m14, m15, and m16 each independently represent an integer of 0 or 1 or more, and m11+m12+m13+m14+m15+m16 is preferably an integer of 2 to 200.
  • the bonding order of (OG f1 ) to (OG f6 ) in structure (f2) is arbitrary.
  • m11 to m16 in structure (f2) respectively represent the number of (OG f1 ) to (OG f6 ), and do not represent the arrangement.
  • (OG f5 ) m15 represents that the number of (OG f5 ) is m15, and does not represent a block arrangement structure of (OG f5 ) m15 .
  • the order of (OG f1 ) to (OG f6 ) does not represent the bonding order of each unit.
  • the fluoroalkylene group having 3 to 6 carbon atoms may be a straight-chain fluoroalkylene group, or a fluoroalkylene group having a branched or cyclic structure.
  • G f1 include --CF 2 -- and --CHF--.
  • G f2 include -CF 2 CF 2 -, -CHFCF 2 -, -CHFCHF-, -CH 2 CF 2 -, and -CH 2 CHF-.
  • G f3 include -CF 2 CF 2 CF 2 -, -CF 2 CHFCF 2 -, -CF 2 CH 2 CF 2 -, -CHFCF 2 CF 2 -, -CHFCHFCF 2 -, -CHFCHFCHF-, -CHFCH 2 CF 2 -, -CH 2 CF 2 CF 2 -, -CH 2 CHFCF 2 -, -CH 2 CH 2 CF 2 -, -CH 2 CF 2 CHF-, -CH 2 CHFCHF-, -CH 2 CH 2 CHF-, -CF(CF 3 )-CF 2 -, -CF( CHF2 ) -CF2- , -CF( CH2F ) -CF2 -, -CF(CH 3 )-CF 2 -, -CF(CF 3 )-CHF-, -CF(CHF 2 )-CHF-, -CF(CH 3 )-CF 2 -, -CF(
  • G f4 examples include -CF 2 CF 2 CF 2 CF 2 -, -CHFCF 2 CF 2 CF 2 -, -CH 2 CF 2 CF 2 -, -CF 2 CHFCF 2 CF 2 -, -CHFCHF 2 CF 2 -, -CH 2 CHFCF 2 CF 2 -, -CF 2 CH 2 CF 2 CF 2 -, -CHFCH 2 CF 2 CF 2 -, -CH 2 CH 2 CF 2 CF 2 -, -CHFCF 2 CHFCF 2 -, -CH 2 CHFCF 2 -, -CF 2 CHFCHF 2 -, -CHFCHFCHFCF 2 -, -CH 2 CHFCHF 2 -, -CF 2 CH 2 CHFCF 2 -, -CHFCH 2 CHFCF 2 -, -CH 2 CH 2 CHFCF 2 -, -CF 2 CH 2 CH 2 Examples include CF 2 -,
  • G f5 examples include -CF 2 CF 2 CF 2 CF 2 CF 2 -, -CHFCF 2 CF 2 CF 2 -, -CH 2 CHFCF 2 CF 2 CF 2 -, -CF 2 CHFCF 2 CF 2 CF 2 - , -CHFCHFCF2CF2CF2- , -CF2CH2CF2CF2CF2- , -CHFCH2CF2CF2CF2- , -CH2CH2CF2CF2CF2- , -CF2CF 2 CHFCF 2 CF 2 -, -CHFCF 2 Examples thereof include CHFCF 2 CF 2 --, --CH 2 CF 2 CHFCF 2 CF 2 --, --CH 2 CF 2 CF 2 CH 2 --, and --cycloC 5 F 8 --.
  • Gf6 examples include -CF2CF2CF2CF2CF2CF2CF2- , -CF2CF2CHFCHFCF2CF2CF2- , -CHFCF2CF2CF2CF2CF2CF2CF2- , -CHFCHFCHFCHFCHFCHF- , -CHFCF2CF2CF2CF2CF2CF2CH2- , -CH2CF2CF2CF2CF2CH2- , -cycloC6F10- .
  • -cycloC 4 F 6 - means a perfluorocyclobutanediyl group, specific examples of which include a perfluorocyclobutane-1,2-diyl group and a perfluorocyclobutane-1,3-diyl group.
  • -cycloC 5 F 8 - means a perfluorocyclopentanediyl group, specific examples of which include a perfluorocyclopentane-1,3-diyl group.
  • -cycloC 6 F 10 - means a perfluorocyclohexanediyl group, specific examples of which include a perfluorocyclohexane-1,4-diyl group.
  • -(OR f12 ) m1 - and -(OR f22 ) m2 - preferably have any of the structures represented by the following structures (f3) to (f5), and in view of superior alkali resistance, more preferably have a structure represented by structure (f3), and even more preferably have a structure represented by (OCF 2 ) m11 .(OCF 2 CF 2 ) m12 .
  • m12/m11 is preferably 0.1 to 10, more preferably 0.2 to 5.0, even more preferably 0.2 to 2.0, particularly preferably 0.2 to 1.5, and most preferably 0.2 to 0.85, in view of superior abrasion resistance and fingerprint removability of the surface layer.
  • the order of bonding between (OG f1 ) and (OG f2 ), between (OG f2 ) and (OG f4 ) is arbitrary.
  • (OG f1 ) and (OG f2 ) may be arranged alternately, and (OG f1 ) and (OG f2 ) may be arranged in blocks, or may be arranged randomly.
  • m11 is preferably an integer of 1 to 30, and more preferably an integer of 1 to 20.
  • m12 is preferably an integer of 1 to 30, and more preferably an integer of 1 to 20.
  • m12 is preferably an integer of 1 to 30, and more preferably an integer of 1 to 20.
  • m14 is preferably an integer of 1 to 30, and more preferably an integer of 1 to 20.
  • m13 is preferably an integer of 1 to 30, and more preferably an integer of 1 to 20.
  • the proportion of fluorine atoms in the fluoropolyether chains -(OR f12 ) m1 - and -(OR f22 ) m2 - [ ⁇ number of fluorine atoms/(number of fluorine atoms+number of hydrogen atoms) ⁇ 100(%)] is preferably 60% or more, more preferably 70% or more, and even more preferably 80% or more, from the viewpoint of abrasion resistance.
  • the molecular weight of the fluoropolyether chain -(OR f12 ) m1 - and -(OR f22 ) m2 - portions is preferably from 2,000 to 20,000, more preferably from 2,500 to 15,000, and even more preferably from 3,000 to 10,000, from the viewpoint of abrasion resistance.
  • Q1 is a (n3+n2)-valent linking group
  • Q2 is a (1+n2)-valent linking group.
  • Q1 will be described below as a representative example.
  • Q1 may be any group that does not impair the effects of the present disclosure, and examples thereof include an alkylene group which may have an etheric oxygen atom or a divalent organopolysiloxane group, a carbon atom, a nitrogen atom, a silicon atom, a divalent to octavalent organopolysiloxane group, and groups obtained by removing J1 (i.e., group P) from groups (3-1A), (3-1B), and (3-1A-1) to (3-1A-7) described below.
  • group P group obtained by removing J1 (i.e., group P) from groups (3-1A), (3-1B), and (3-1A-1) to (3-1A-7) described below.
  • Q1 may be any of the groups (g2-1) to (g2-14) described below.
  • n2 is an integer of 1 or more.
  • n2 is preferably 1 to 15, more preferably 1 to 6, even more preferably 2 to 4, and particularly preferably 2 or 3.
  • n3 is an integer of 1 or more. In order to provide a surface treatment layer with superior abrasion resistance, n3 is preferably 1 to 3, and more preferably 1.
  • the group represented by -Q 1 -(J 1 ) n2 in formula (1) is preferably the following group (3-1A) or (3-1B), more preferably group (3-1A).
  • Q a is a single bond or a divalent linking group.
  • the divalent linking group include a divalent hydrocarbon group, a divalent heterocyclic group, -O-, -S-, -SO 2 -, -N(R d )-, -C(O)-, -Si(R a ) 2 -, and groups formed by combining two or more of these.
  • the divalent hydrocarbon group may be a divalent saturated hydrocarbon group, a divalent aromatic hydrocarbon group, an alkenylene group, or an alkynylene group.
  • the divalent saturated hydrocarbon group may be linear, branched, or cyclic, and may be, for example, an alkylene group.
  • the number of carbon atoms in the alkylene group is preferably 1 to 30, more preferably 1 to 20, even more preferably 4 to 20, and particularly preferably 5 to 15.
  • the divalent aromatic hydrocarbon group is preferably one having 5 to 20 carbon atoms, and may be, for example, a phenylene group.
  • the divalent aromatic hydrocarbon group may be an alkenylene group having 2 to 20 carbon atoms, or an alkynylene group having 2 to 20 carbon atoms.
  • the above R a is an alkyl group (preferably having 1 to 10 carbon atoms) or a phenyl group
  • the above R d is a hydrogen atom or an alkyl group (preferably having 1 to 10 carbon atoms).
  • groups combining two or more of these groups include -OC(O)-, -C(O)O-, -C(O)S-, -C(O)N(R d )-, -N(R d )C(O)-, -N(R d )C(O)N(R d )-, -N(R d )C( O )O-, -OC(O)N(R d )-, -SO 2 N(R d )-, -N(R d )SO 2 -, an alkylene group having -C(O)N(R d )-, an alkylene group having -N(R d )C(O)-, -OC(O)N(R d )-, an alkylene group having an etheric oxygen atom, an alkylene group having -S-, an alkylene group having -OC(O)-, an alkylene group having -C(O
  • Q a is a divalent hydrocarbon group other than an alkylene group, a divalent heterocyclic group, an alkylene group having —O—, —S—, —SO 2 —, —N(R d )—, —C(O)—, —Si(R a ) 2 —, —OC(O)—, —C(O)O—, —C(O)S—, —C(O)N(R d )—, —N(R d )C(O)—, —N(R d )C(O)N(R d )—, —N(R d )C(O)O—, —OC(O)N(R d )—, —SO 2 N(R d )—, —N(R d )SO 2 —, —C(O)N(R d )—, —N(R d )C(O)-, an alkylene
  • X 31 represents a single bond, an alkylene group, a carbon atom, a nitrogen atom, a silicon atom, a divalent to octavalent organopolysiloxane group, or a group having a (h+i+1)-valent ring.
  • the alkylene group may have, between carbon atoms, -O-, a silphenylene skeleton group, a divalent organopolysiloxane group, or a dialkylsilylene group.
  • the alkylene group may have a plurality of groups selected from the group consisting of -O-, a silphenylene skeleton group, a divalent organopolysiloxane group, and a dialkylsilylene group.
  • the alkylene group represented by X 31 preferably has 1 to 20 carbon atoms, and more preferably has 1 to 10 carbon atoms.
  • Examples of the divalent to octavalent organopolysiloxane group include a divalent organopolysiloxane group and a (w2+1)-valent organopolysiloxane group described below.
  • X 31 when X 31 is a group having a (h+i+1)-valent ring, Q a , (-Q b -J 1 ) and R 31 are directly bonded to atoms constituting the ring, provided that the ring is a ring other than an organopolysiloxane ring.
  • the ring in X31 may be any of a monocycle, a condensed polycycle, a bridged ring, a spiro ring, and an aggregate polycycle, and the atoms constituting the ring may be a carbon ring consisting of only carbon atoms, or a heterocycle consisting of a heteroatom having a valence of 2 or more and a carbon atom.
  • the bond between the atoms constituting the ring may be a single bond or a multiple bond.
  • the ring may be an aromatic ring or a non-aromatic ring.
  • a 4- to 8-membered ring is preferred, and a 5-membered ring and a 6-membered ring are more preferred.
  • condensed polycyclic ring a condensed polycyclic ring in which two or more 4- to 8-membered rings are condensed is preferred, and a condensed polycyclic ring in which two or three rings selected from a 5-membered ring and a 6-membered ring are bonded, and a condensed polycyclic ring in which one or two rings selected from a 5-membered ring and a 6-membered ring are bonded to one 4-membered ring are more preferred.
  • each ring is preferably bonded to any one of Q a , (-Q b -J 1 ) and R 31 (when i is 1 or more).
  • the heteroatoms constituting the ring are preferably nitrogen, oxygen and sulfur atoms, more preferably nitrogen and oxygen atoms.
  • the number of heteroatoms constituting the ring is preferably 3 or less. In addition, when the number of heteroatoms constituting the ring is 2 or more, the heteroatoms may be different.
  • the ring for X 31 from the viewpoints of ease of production of the compound and further superior abrasion resistance of the surface treatment layer, it is preferable to use one selected from the group consisting of a 3- to 8-membered aliphatic ring, a benzene ring, a 3- to 8-membered heterocycle, a condensed ring in which two or three of these rings are condensed, a bridged ring in which the maximum ring is a 5- or 6-membered ring, and an assembled polycycle having two or more of these rings and in which the linking group is a single bond, an alkylene group having 3 or less carbon atoms, an oxygen atom, or a sulfur atom.
  • Preferred rings are a benzene ring, a 5- or 6-membered aliphatic ring, a 5- or 6-membered heterocycle having a nitrogen atom or an oxygen atom, and a condensed ring of a 5- or 6-membered carbocycle with a 4- to 6-membered heterocycle.
  • a bond not constituting a ring of an atom in X 31 is a bond bonded to Q a , (-Q b -J 1 ), or R 31.
  • the remaining bond is bonded to a hydrogen atom or a substituent.
  • the substituent include a halogen atom, an alkyl group (which may contain an etheric oxygen atom between the carbon-carbon atom), a cycloalkyl group, an alkenyl group, an allyl group, an alkoxy group, and an oxo group ( ⁇ O).
  • Q a and (-Q b -J 1 ) may be bonded to that one carbon atom, or two (-Q b -J 1 ) may be bonded to that one carbon atom. It is preferable that Q a is bonded to a ring-constituting atom different from (-Q b -J 1 ) or R 31.
  • the h (-Q b -J 1 ) may be bonded to different ring-constituting atoms, two of which may be bonded to one ring-constituting carbon atom, and there may be two or more ring-constituting carbon atoms to which two (-Q b -J 1 ) are bonded.
  • the i R 31 may be bonded to different ring-constituting atoms, two of which may be bonded to one ring-constituting carbon atom, and there may be two or more ring-constituting carbon atoms to which two R 31 are bonded.
  • X 31 is preferably a carbon atom, a nitrogen atom, a silicon atom, a tetravalent to octavalent organopolysiloxane group, or a group having a (h+i+1)-valent ring, and more preferably a carbon atom.
  • Qb is a single bond or a divalent linking group.
  • the divalent linking group is the same as that explained above for Qa .
  • Q b is preferably an alkylene group which may have an etheric oxygen atom.
  • the number of carbon atoms in the alkylene group is preferably 1 to 30, more preferably 1 to 20, and still more preferably 2 to 20, and may be 2 to 10, 2 to 6, or 2 to 5. Examples include 2, 3, 8, 9, and 11. The number of carbon atoms may be 1 to 10.
  • R 31 is a hydrogen atom, a hydroxyl group or an alkyl group.
  • the alkyl group preferably has 1 to 5 carbon atoms, more preferably 1 to 3 carbon atoms, and even more preferably 1 carbon atom.
  • X 31 is a group having a (h+i+1)-valent ring
  • h is an integer of 1 to 7
  • i is an integer of 0 to 6
  • the two or more (-Q b -J 1 ) may be the same or different.
  • the two or more (-R 31 s ) may be the same or different.
  • i 0.
  • Q c is a single bond or a divalent linking group.
  • the divalent linking group in Qc is the same as that explained above in relation to Qa .
  • R 32 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and is preferably a hydrogen atom in terms of ease of production of the compound.
  • the alkyl group is preferably a methyl group.
  • Q d is a single bond or an alkylene group.
  • the number of carbon atoms in the alkylene group is preferably 1 to 10, and more preferably 1 to 6. From the viewpoint of ease of production of the compound, Q d is preferably a single bond or CH 2 —.
  • R 33 is a hydrogen atom or a halogen atom, and is preferably a hydrogen atom in terms of ease of production of the compound.
  • y is an integer of 1 to 10, and preferably an integer of 1 to 6.
  • Two or more [CH 2 C(R 32 )(-Q d -J 1 )] may be the same or different.
  • the following groups (3-1A-1) to (3-1A-7) are preferable.
  • group (3-1A) is preferably group (3-1A-4).
  • Z1 is a single bond or an alkylene group which may have an oxygen atom between carbon atoms.
  • alkylene group examples include the alkylene groups exemplified as the divalent linking group represented by Qa , and the preferred embodiments are also the same.
  • X 32 is —O—, —S—, —N(R d )—, —C(O)—, —C(O)O—, —C(O)S—, —SO 2 N(R d )—, —N(R d )SO 2 —, —N(R d )C(O)—, —N(R d )C(O)N(R d )—, —OC(O)N(R d )—, or —C(O)N(R d )— (wherein N in the formula is bonded to Q b1 ).
  • the definition of Rd is as described above. s1 is 0 or 1.
  • X 32 is preferably —O—, —S—, —N(R d )—, —C(O)—, —C(O)O—, —C(O)S—, —SO 2 N(R d )—, —N(R d )SO 2 —, —N(R d )C(O)—, —N(R d )C(O)N(R d )—, —OC(O)N(R d )—, or —C(O)N(R d )—, and more preferably —O—, —S—, —N(R d )—, —C(O)O—, —C(O)S—, —N(R d )C(O)N(R d )—, —OC(O)N(R d )—, or —C(O)N(R d ).
  • )- is more preferred, and
  • Q b1 is a single bond or an alkylene group.
  • the alkylene group may have -O-, a silphenylene skeleton group, or a dialkylsilylene group.
  • the alkylene group may have a plurality of groups selected from the group consisting of -O-, a silphenylene skeleton group, a divalent organopolysiloxane group, and a dialkylsilylene group.
  • the alkylene group has --O--, a silphenylene skeleton group, a divalent organopolysiloxane group, or a dialkylsilylene group, it is preferable that such a group be present between carbon atoms.
  • the alkylene group represented by Q b1 has preferably 1 to 30 carbon atoms, more preferably 1 to 20, still more preferably 2 to 20, and particularly preferably 2 to 6. The number of carbon atoms may be 1 to 10.
  • Q b1 is preferably an alkylene group having 2 to 6 carbon atoms.
  • -(X 32 ) s1 -Q b1 -J 1 in the group (3-1A-1) include the following groups:
  • * represents the bonding position with Z 1 .
  • X33 is -O-, -S-, -N(R d )-, -C(O)-, -C(O)O-, -C(O)S-, -SO 2 N(R d )-, -N(R d )SO 2 -, -N(R d )C(O)-, -N( R d )C(O)N(R d )-, -OC(O)N(R d )-, or -C(O)N(R d )-.
  • Rd is as described above.
  • s2 is 0 or 1.
  • s2 is preferably 0 from the viewpoint of ease of production of the compound.
  • X 33 is preferably —O—, —S—, —N(R d )—, —C(O)—, —C(O)O—, —C(O)S—, —SO 2 N(R d )—, —N(R d )SO 2 —, —N(R d )C(O)—, —N(R d )C(O)N(R d )—, —OC(O)N(R d )— or —C(O)N(R d )—, more preferably —C(O)O—, —C(O)S—, —SO 2 N(R d )— or —C(O)N(R d )—.
  • Q a2 is a single bond, an alkylene group, -C(O)-, or an alkylene group having 2 or more carbon atoms having an ether oxygen atom between carbon atoms, -C(O)-, -C(O)O-, -OC(O)-, -C(O)N(R d )-, -N( R d )C(O)-, -N(R d )C(O)N(R d )-, -N(R d )C(O)O-, -OC(O)N(R d )-, -SO 2 N(R d )-, -N(R d )SO 2 -, -C(O)N(R d )-, or -NH-.
  • the alkylene group represented by Q a2 preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, further preferably 1 to 6 carbon atoms, and particularly preferably 1 to 3 carbon atoms.
  • Q a2 is preferably a single bond from the viewpoint of ease of production of the compound.
  • Q b2 is an alkylene group or an alkylene group having 2 or more carbon atoms which has a divalent organopolysiloxane group, an ether oxygen atom or an --NH-- group between carbon atoms.
  • the number of carbon atoms in the alkylene group represented by Q b2 is preferably 1 to 30, more preferably 1 to 20, and still more preferably 2 to 20, and may be 2 to 10 or may be 2 to 6. Examples include 2, 3, 8, 9, and 11. The number of carbon atoms may be 1 to 10.
  • the alkylene group having 2 or more carbon atoms represented by Q b2 preferably has 2 to 10 carbon atoms, and more preferably has 2 to 6 carbon atoms, in the divalent organopolysiloxane group, the group having an ether oxygen atom or an --NH-- group between carbon atoms.
  • --CH 2 CH 2 CH 2 -- and --CH 2 CH 2 OCH 2 CH 2 CH 2 -- are preferred (wherein the right side is bonded to Si).
  • the two [-Q b2 -J 1 ] may be the same or different.
  • -(X 33 ) s2 -Q a2 -N[-Q b2 -J 1 ] 2 in the group (3-1A-2) include the following groups.
  • * represents the bonding position with Z 1.
  • ⁇ in (CH 2 ) ⁇ bonding to J 1 is an integer representing the number of methylene groups, and is preferably 1 to 30, more preferably 1 to 20, and even more preferably 2 to 20, and may be 2 to 10 or may be 2 to 6.
  • 2, 3, 8, 9, and 11 are included.
  • the number of carbon atoms may be 1 to 10.
  • Multiple ⁇ contained in the same compound may be the same or different, but are preferably the same.
  • multiple ⁇ contained in the same compound are all 2, 3, 8, 9, and 11. The same applies below.
  • Q a3 is a single bond or an alkylene group which may have an etheric oxygen atom. From the viewpoint of ease of production of the compound, Q a3 is preferably a single bond.
  • the alkylene group which may have an etheric oxygen atom preferably has 1 to 10 carbon atoms, and particularly preferably has 2 to 6 carbon atoms.
  • Rg is a hydrogen atom, a hydroxyl group or an alkyl group. From the viewpoint of ease of production of the compound, Rg is preferably a hydrogen atom or an alkyl group.
  • the alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 4 carbon atoms, and further preferably is a methyl group.
  • Q b3 is an alkylene group or a group having an ether oxygen atom or a divalent organopolysiloxane group between carbon atoms in an alkylene group having 2 or more carbon atoms.
  • the number of carbon atoms in the alkylene group represented by Q b3 is preferably 1 to 30, more preferably 1 to 20, and still more preferably 2 to 20, and may be 2 to 10 or may be 2 to 6. Examples include 2, 3, 8, 9, and 11. The number of carbon atoms may be 1 to 10.
  • the group having an ether oxygen atom or a divalent organopolysiloxane group between carbon atoms of the alkylene group having 2 or more carbon atoms, represented by Q b3 preferably has 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms, and even more preferably 2 to 6 carbon atoms.
  • Q b3 is preferably -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, or -CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 - from the viewpoint of ease of production of the compound.
  • the two [-Q b3 -J 1 ] may be the same or different.
  • --Si( R.sup.g )[- Q.sub.b3 - J.sub.1 ] .sub.2 in the group (3-1A-3) include the following groups: In the following formula, * represents the bonding position with Q.sub.a3 .
  • Q e is —C(O)O—, —SO 2 N(R d )—, —N(R d )SO 2 —, —N(R d )C(O)—, or —C(O)N(R d )—.
  • R 31 is as described above. When w1 is 1 or 2, R 31 is preferably a hydrogen atom.
  • s4 is 0 or 1.
  • Q a4 is a single bond or an alkylene group which may have an etheric oxygen atom.
  • the alkylene group which may have an etheric oxygen atom preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, further preferably 1 to 6 carbon atoms, and particularly preferably 1 to 3 carbon atoms.
  • t4 is 0 or 1 (provided that when Q a4 is a single bond, t4 is 0).
  • s4 when s4 is 0, a single bond, -CH 2 O-, -CH 2 OCH 2 -, -CH 2 OCH 2 CH 2 OCH 2 -, -CH 2 OCH 2 CH 2 OCH 2 -, or -CH 2 OCH 2 CH 2 CH 2 OCH 2 - is preferred (with the left side bonding to Q e ), and when s4 is 1, a single bond, -CH 2 -, or -CH 2 CH 2 - is preferred.
  • Q b4 is an alkylene group, and the alkylene group may have -O-, -C(O)N(R d )- (R d is as defined above), a silphenylene skeleton group, a divalent organopolysiloxane group, or a dialkylsilylene group.
  • R d is as defined above
  • the alkylene group has -O- or a silphenylene skeleton group, it is preferable that the alkylene group has the -O- or silphenylene skeleton group between carbon atoms.
  • the alkylene group has -C(O)N(R d )-, a dialkylsilylene group, or a divalent organopolysiloxane group
  • the alkylene group has the -C(O)N(R d )- group between carbon atoms or at the end of the side bonded to (O) u4 .
  • the number of carbon atoms in the alkylene group represented by Q b4 is preferably 1 to 30, more preferably 1 to 20, and still more preferably 2 to 20, and may be 2 to 10 or may be 2 to 6. Examples include 2, 3, 8, 9, and 11. The number of carbon atoms may be 1 to 10.
  • u4 is 0 or 1.
  • -(O) u4 -Q b4 - -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -CH 2 OCH 2 CH 2 CH 2 -, -CH 2 OCH 2 CH 2 CH 2 CH 2 CH 2 CH 2 -, -OCH 2 CH 2 CH 2 - , -OSi(CH 3 ) 2 CH 2 CH 2 CH 2 -, -OSi(CH 3 ) 2 OSi(CH 3 ) 2 CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 Si ( CH 3 ) 2 PhSi(CH 3 ) 2 CH 2 CH 2 - are preferred from the viewpoint of ease of production of the compound (wherein the right side is bonded to Si).
  • w1 represents an integer of 0 to 2, preferably 0 or 1, and particularly preferably 0.
  • the two or more [-(O) u4 -Q b4 -J 1 ] may be the same or different.
  • the two or more (-R 31 s ) may be the same or different.
  • Q a5 is an alkylene group which may have an etheric oxygen atom.
  • the alkylene group which may have an etheric oxygen atom preferably has 1 to 10 carbon atoms, and particularly preferably has 2 to 6 carbon atoms.
  • Q a5 from the viewpoint of ease of production of the compound, -OCH 2 CH 2 CH 2 -, -OCH 2 CH 2 OCH 2 CH 2 CH 2 -, -CH 2 CH 2 - and -CH 2 CH 2 CH 2 - are preferred (wherein the right side is bonded to Si).
  • Q b5 is an alkylene group or a group having an ether oxygen atom or a divalent organopolysiloxane group between carbon atoms in an alkylene group having 2 or more carbon atoms.
  • the number of carbon atoms in the alkylene group represented by Q b5 is preferably 1 to 30, more preferably 1 to 20, and still more preferably 2 to 20, and may be 2 to 10 or may be 2 to 6. Examples include 2, 3, 8, 9, and 11. The number of carbon atoms may also be 1 to 10.
  • the group having an ether oxygen atom or a divalent organopolysiloxane group between carbon atoms of the alkylene group having 2 or more carbon atoms, represented by Q b5 preferably has 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms, and even more preferably 2 to 6 carbon atoms.
  • Q b5 is preferably --CH 2 CH 2 CH 2 -- or --CH 2 CH 2 OCH 2 CH 2 CH 2 -- (wherein the right side bonds to J1 ) in terms of ease of production of the compound.
  • the three [-Q b5 -J 1 ] may be the same or different.
  • group (3-1A-5) include the following groups:
  • * represents the bonding position with R f1 .
  • Q a6 is an alkylene group which may have an etheric oxygen atom.
  • the alkylene group which may have an etheric oxygen atom preferably has 1 to 10 carbon atoms, and particularly preferably has 2 to 6 carbon atoms.
  • Q a6 —CH 2 OCH 2 CH 2 CH 2 —, —CH 2 OCH 2 CH 2 OCH 2 CH 2 CH 2 —, —CH 2 CH 2 — or —CH 2 CH 2 CH 2 — is preferred from the viewpoint of ease of production of the compound ( wherein the right side bonds to Z a ).
  • Z a is a (w2+1)-valent organopolysiloxane group or a (w2+1)-valent group having an alkylene group between the organopolysiloxane groups.
  • w2 is an integer from 2 to 7.
  • Examples of the (w2+1)-valent organopolysiloxane group and the (w2+1)-valent group having an alkylene group between the organopolysiloxane groups include the following groups, where R a in the following formula is as defined above. * indicates a bonding site.
  • Q b6 is an alkylene group or a group having an ether oxygen atom or a divalent organopolysiloxane group between carbon atoms in an alkylene group having 2 or more carbon atoms.
  • the number of carbon atoms in the alkylene group represented by Q b6 is preferably 1 to 30, more preferably 1 to 20, and still more preferably 2 to 20, and may be 2 to 10 or may be 2 to 6. Examples include 2, 3, 8, 9, and 11. The number of carbon atoms may be 1 to 10.
  • the group having an ether oxygen atom or a divalent organopolysiloxane group between carbon atoms of the alkylene group having 2 or more carbon atoms, represented by Q b6 preferably has 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms, and even more preferably 2 to 6 carbon atoms.
  • Q b6 is preferably —CH 2 CH 2 — or —CH 2 CH 2 CH 2 — from the viewpoint of ease of production of the compound.
  • the w2 groups [-Q b6 -J 1 ] may be the same or different.
  • Zc is a (w3+w4+1)-valent hydrocarbon group.
  • w3 is an integer of 4 or greater.
  • w4 is an integer of 0 or greater.
  • the definitions and preferred ranges of Q e , s4, Q a4 , t4, Q b4 and u4 are the same as those of each symbol in the group (3-1A-4).
  • Zc may be composed of a hydrocarbon chain, and may have an ether oxygen atom between carbon atoms of the hydrocarbon chain, and is preferably composed of a hydrocarbon chain.
  • the valence of Zc is preferably from 5 to 20, more preferably from 5 to 10, further preferably from 5 to 8, and particularly preferably from 5 to 6.
  • Zc preferably has 3 to 50 carbon atoms, more preferably 4 to 40 carbon atoms, and even more preferably 5 to 30 carbon atoms.
  • w3 is preferably 4 to 20, more preferably 4 to 16, still more preferably 4 to 8, and particularly preferably 4 or 5.
  • w4 is preferably an integer of 0 to 10, more preferably an integer of 0 to 8, still more preferably an integer of 0 to 6, particularly preferably an integer of 0 to 3, and most preferably an integer of 0 to 1.
  • the two or more [-(OQ b4 ) u4 -J 1 ] may be the same or different.
  • A1 is bonded to R f1 , and Q 22 , Q 23 , Q 24 , Q 25 or Q 26 is bonded to J 1 .
  • a 1 is a single bond, —C(O)NR e6 —, —C(O)—, —OC(O)O—, —NHC(O)O—, —NHC(O)NR e6 —, —O— or SO 2 NR e6 —.
  • Q12 is a single bond, an alkylene group, or a group having -C(O) NR6- , -C(O)-, -NR6- or O- between carbon atoms in an alkylene group having 2 or more carbon atoms, and when there are two or more Q12 , the two or more Q12 may be the same or different.
  • Q13 is a single bond (with the proviso that Q1 is -C(O)-), an alkylene group, an alkylene group having 2 or more carbon atoms having -C(O) NR6- , -C(O)-, -NR6- or O- between carbon atoms, or an alkylene group having -C(O)- at the N-terminal.
  • Q14 is Q12 when the atom in Z to which Q14 is bonded is a carbon atom, and is Q13 when the atom in Z to which Q14 is bonded is a nitrogen atom.
  • the two or more Q14s may be the same or different.
  • Q15 is an alkylene group or a group having -C(O) NR6- , -C(O)-, -NR6- or O- between carbon atoms in an alkylene group having 2 or more carbon atoms, and when there are two or more Q15s , the two or more Q15s may be the same or different.
  • Q 22 is an alkylene group, a group having -C(O)NR 6 -, -C(O)-, -NR 6 - or O- between the carbon-carbon atoms of an alkylene group having 2 or more carbon atoms, a group having -C(O)NR 6 -, -C(O)-, -NR 6 - or O- at the end of the alkylene group not connected to Si, or a group having -C(O)NR 6 -, -C(O)-, -NR 6 - or O- between the carbon-carbon atoms of an alkylene group having 2 or more carbon atoms and having -C(O)NR 6 -, -C(O)-, -NR 6 - or O- at the end of the side not connected to Si, and when there are two or more Q 22 , the two or more Q 22 may be the same or different.
  • Q 23 is an alkylene group or a group having --C(O)NR 6 --, --C(O)--, --NR 6 -- or O-- between carbon atoms of an alkylene group having 2 or more carbon atoms, and two Q 23 's may be the same or different.
  • Q24 is Q22 when the atom in Z to which Q24 is bonded is a carbon atom, and is Q23 when the atom in Z to which Q24 is bonded is a nitrogen atom. When there are two or more Q24s, the two or more Q24s may be the same or different.
  • Q25 is an alkylene group or a group having -C(O) NR6- , -C(O)-, -NR6- or O- between carbon atoms of an alkylene group having 2 or more carbon atoms, and when there are two or more Q25s , the two or more Q25s may be the same or different.
  • Q 26 is an alkylene group or an alkylene group having 2 or more carbon atoms having --C(O)NR 6 --, --C(O)--, --NR 6 -- or O-- between carbon atoms.
  • Q 22 , Q 23 , Q 24 , Q 25 and Q 26 are each an alkylene group, they preferably have 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, and even more preferably 1 to 6 carbon atoms.
  • Z is a group having a (h1+h2)-valent ring structure having a carbon atom or nitrogen atom to which Q 14 is directly bonded, and having a carbon atom or nitrogen atom to which Q 24 is directly bonded.
  • R e1 is a hydrogen atom or an alkyl group, and when two or more R e1 are present, the 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 6 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.
  • d1 is an integer of 0 to 3, and is preferably 1 or 2.
  • d2 is an integer of 0 to 3, and is preferably 1 or 2.
  • d1+d2 is an integer from 1 to 3.
  • d3 is an integer of 0 to 3, and is preferably 0 or 1.
  • d4 is an integer of 0 to 3, and is preferably 2 or 3.
  • d3+d4 is an integer from 1 to 3.
  • d1+d3 is an integer of 1 to 5, and is preferably 1 or 2.
  • d2+d4 is an integer of 1 to 5, and is preferably 2 or 3.
  • e1+e2 is 3 or 4.
  • e1 is an integer of 1 to 3, and is preferably 1 or 2.
  • e2 is an integer of 1 to 3, and is preferably 2 or 3.
  • h1 is an integer of 1 or more, and is preferably 1 or 2.
  • h2 is an integer of 1 or more, and is preferably 2 or 3.
  • i1+i2 is 3 or 4.
  • i1 is an integer of 1 to 3, and is preferably 1 or 2.
  • i2 is an integer of 1 to 3, and is preferably 2 or 3.
  • i3 is 2 or 3.
  • the number of carbon atoms of the alkylene group of Q 12 , Q 13 , Q 14 , Q 15 , Q 22 , Q 23 , Q 24 , Q 25 and Q 26 is preferably 1 to 30, more preferably 1 to 20, and even more preferably 2 to 20, from the viewpoint of ease of production of the compound and further superior wear resistance of the surface treatment layer, and may be 2 to 10 or 2 to 6. Examples include 2, 3, 8, 9 and 11.
  • the number of carbon atoms may be 1 to 10, 1 to 6 or 1 to 4. However, the lower limit of the number of carbon atoms of the alkylene group in the case where a specific bond is present between the carbon-carbon atom is 2.
  • Examples of the ring structure in Z include the ring structures described above, and the preferred forms are also the same. Since Q 14 and Q 24 are directly bonded to the ring structure in Z, for example, an alkylene group is not bonded to the ring structure and Q 14 and Q 24 are not bonded to the alkylene group.
  • the number of carbon atoms in the alkyl group of R e1 , R e2 or R e3 is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 or 2, from the viewpoint of ease of production of the compound.
  • the number of carbon atoms in the alkyl group portion of the acyloxy group for R e2 is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 or 2, from the viewpoint of ease of production of the compound.
  • h1 is preferably 1 to 6, more preferably 1 to 4, still more preferably 1 or 2, and particularly preferably 1, from the viewpoints of ease of production of the compound and of further improving the abrasion resistance of the surface treatment layer.
  • 2 to 6 are preferable, 2 to 4 are more preferable, and 2 or 3 is particularly preferable.
  • G 1 is the following group (g3), and two or more G 1s in Q 1 may be the same or different.
  • the symbols other than G 1 are the same as the symbols in formulae (g2-1) to (g2-7).
  • the Si side is connected to Q 22 , Q 23 , Q 24 , Q 25 and Q 26 , and the Q 3 side is connected to J 1.
  • R 8 is an alkyl group.
  • Q 3 is an alkylene group, a group having -C(O)NR 6 -, -C(O)-, -NR 6 - or -O- between the carbon-carbon atoms of an alkylene group having 2 or more carbon atoms, or (OSi(R 9 ) 2 ) p -O-, and two or more Q 3s may be the same or different.
  • k3 is 2 or 3.
  • R 6 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a phenyl group.
  • R 9 is an alkyl group, a phenyl group or an alkoxy group, and two R 9s may be the same or different.
  • p is an integer of 0 to 5, and when p is 2 or more, the two or more (OSi(R 9 ) 2 ) may be the same or different.
  • the number of carbon atoms in the alkylene group of Q3 is preferably 1 to 30, more preferably 1 to 20, and even more preferably 2 to 20, from the viewpoints of ease of production of the compound and further superior abrasion resistance of the surface treatment layer, and may be 2 to 10 or 2 to 6. Examples include 2, 3, 8, 9, and 11.
  • the number of carbon atoms may be 1 to 10, 1 to 6, or 1 to 4.
  • the lower limit of the number of carbon atoms in the alkylene group in the case where a specific bond is present between a carbon-carbon atom is 2.
  • the number of carbon atoms in the alkyl group of R 8 is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 or 2, from the viewpoint of ease of production of the compound.
  • the number of carbon atoms in the alkyl group of R 9 is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 or 2, from the viewpoint of ease of production of the compound.
  • the number of carbon atoms in the alkoxy group of R 9 is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 or 2, in terms of excellent storage stability of the compound.
  • p is preferably 0 or 1.
  • Examples of the compound of the present disclosure include a compound of the following formula.
  • the compound of the following formula is preferred because it is easy to produce industrially, easy to handle, and provides a surface treatment layer with even better water repellency and abrasion resistance.
  • Rt in the compound of the following formula is the same as ( Rf1 ) in formula (1), and the preferred form is also the same.
  • Examples of the compound in which Q 1 in formula (1) is a group (g2-1) include the compounds of the following formula.
  • Examples of compounds in which Q 1 in formula (1) is a group (g2-2) include compounds of the following formula:
  • Ak represents an alkyl group (for example, an alkyl group having 1 to 15 carbon atoms).
  • Examples of the compound in which Q 1 in formula (1) is a group (g2-3) include the compounds of the following formula.
  • Examples of the compound in which Q 1 in formula (1) is a group (g2-4) include the compounds of the following formulae.
  • Examples of the compound in which Q 1 in formula (1) is a group (g2-5) include the compounds of the following formulae.
  • Examples of the compound in which Q 1 in formula (1) is a group (g2-6) include the compounds of the following formula.
  • Examples of the compound in which Q 1 in formula (1) is a group (g2-7) include the compounds of the following formula.
  • Examples of the compound in which Q 1 in formula (1) is a group (g2-8) include the compounds of the following formulae.
  • Examples of the compound in which Q 1 in formula (1) is a group (g2-9) include the compounds of the following formulae.
  • Examples of the compound in which Q 1 in formula (1) is a group (g2-10) include the compounds of the following formulae.
  • Examples of the compound in which Q 1 in formula (1) is a group (g2-11) include the compounds of the following formulae.
  • Examples of the compound in which Q 1 in formula (1) is a group (g2-12) include the compounds of the following formulae.
  • Examples of the compound in which Q 1 in formula (1) is a group (g2-13) include the compounds of the following formulae.
  • Examples of the compound in which Q 1 in formula (1) is a group (g2-14) include the compounds of the following formulae.
  • n is preferably an integer of 1 to 250, more preferably an integer of 5 to 250, and even more preferably an integer of 5 to 50. It may be an integer of 1 to 50, or an integer of 5 to 30.
  • n is 10, 14, 15, 20, 23, or 25.
  • composition of the present disclosure may contain at least one of the compound represented by formula (1) and the compound represented by formula (2), and components other than the compound of the present disclosure (hereinafter also referred to as "other components") are not particularly limited.
  • other components include fluorine-containing compounds other than the compounds of the present disclosure, at least one of the impurities described below, and liquid media.
  • Examples of the other fluorine-containing compound include a fluorine-containing compound produced as a by-product in the production process of the compound (hereinafter also referred to as a "by-product fluorine-containing compound"), a known fluorine-containing compound used for the same purpose as the above-mentioned fluorine-containing ether compound, and the like.
  • a fluorine-containing compound a compound which is unlikely to deteriorate the properties of the compound is preferable.
  • the content of the other fluorine-containing compounds is preferably less than 70 mass%, more preferably less than 50 mass%, even more preferably less than 20 mass%, particularly preferably less than 10 mass%, and most preferably less than 5 mass%, based on the total mass of the surface treatment agent, in order to fully exhibit the properties of the compounds.
  • By-product fluorine-containing compounds include unreacted fluorine-containing compounds during the synthesis of the 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.
  • fluorine-containing compounds examples include those described in the following documents: Perfluoropolyether-modified aminosilanes described in JP-A-11-029585; Silicon-containing organic fluorine-containing polymers as described in Japanese Patent No. 2874715; Organosilicon compounds described in JP-A-2000-144097, Perfluoropolyether-modified aminosilanes described in JP 2000-327772 A; Fluorinated siloxanes described in Japanese Patent Publication No. 2002-506887; Organosilicon compounds described in Japanese Patent Publication No. 2008-534696, Fluorinated modified hydrogen-containing polymers as described in Japanese Patent No. 4138936; Compounds described in U.S. Patent Application Publication No.
  • examples of commercially available fluorine-containing compounds include the KY-100 series (KY-178, KY-185, KY-195, etc.) manufactured by Shin-Etsu Chemical Co., Ltd., the SURECO AF series such as SURECO (registered trademark) 2101S manufactured by AGC, and OPTOOL (registered trademark) DSX, OPTOOL (registered trademark) AES, OPTOOL (registered trademark) UF503, OPTOOL (registered trademark) UD509, OPTOOL (registered trademark) UD120, etc. manufactured by Daikin Industries, Ltd.
  • the content of the other fluorine-containing compounds relative to the total content of the fluorine-containing ether compound and the other fluorine-containing compounds in the present surface treatment agent is preferably 60 mass% or less, more preferably 30 mass% or less, and even more preferably 10 mass% or less.
  • the total content of the fluorinated ether compound and the other fluorinated compounds in the present surface treatment agent is preferably at least 0.01% by mass, more preferably at least 0.03% by mass.
  • the content of the compound of the present disclosure is preferably 0.01 to 50 mass%, more preferably 0.03 to 40 mass%, and even more preferably 0.05 to 30 mass%, based on the total mass of the composition of the present disclosure.
  • the surface treatment layer is more excellent in water and oil repellency, abrasion resistance, fingerprint removability, lubricity, and appearance.
  • the liquid medium contained in the composition of the present disclosure may be only one type, or may be two or more types.
  • an organic solvent is preferred.
  • the organic solvent may be a fluorine-based organic solvent, a non-fluorine-based organic solvent, or may contain both solvents.
  • fluorine-based organic solvent examples include fluorinated alkanes, fluorinated aromatic compounds, fluoroalkyl ethers, fluorinated alkylamines, fluoroalcohols, and hydrofluoroolefins.
  • the fluorinated alkane is preferably a compound having a carbon number of 4 to 8.
  • Commercially available products include C 6 F 13 H (manufactured by AGC, Asahiklin (registered trademark) AC-2000), C 6 F 13 C 2 H 5 (manufactured by AGC, Asahiklin (registered trademark) AC-6000), and C 2 F 5 CHFCHFCF 3 (manufactured by Chemours, Vertrel (registered trademark) XF).
  • fluorinated aromatic compounds include hexafluorobenzene, trifluoromethylbenzene, perfluorotoluene, and bis(trifluoromethyl)benzene.
  • the fluoroalkyl ether is preferably a compound having 4 to 12 carbon atoms.
  • fluorinated alkylamines include perfluorotripropylamine and perfluorotributylamine.
  • fluoroalcohols include 2,2,3,3-tetrafluoropropanol, 2,2,2-trifluoroethanol, and hexafluoroisopropanol.
  • hydrofluoroolefin 1-chloro-2,3,3-trifluoro-1-propene (HCFO-1233yd).
  • a commercially available product is Amorea (registered trademark) AS-300 manufactured by AGC.
  • the non-fluorinated organic solvent a compound consisting only of hydrogen atoms and carbon atoms, and a compound consisting only of hydrogen atoms, carbon atoms and oxygen atoms are preferred, and examples thereof include hydrocarbon organic solvents, alcohol organic solvents, ketone organic solvents, ether organic solvents and ester organic solvents.
  • the present surface treatment agent preferably contains 60 to 99.999 mass %, more preferably 85 to 99.99 mass %, and even more preferably 90 to 99.9 mass % of the liquid medium.
  • the present surface treatment agent may further contain known additives such as an acid catalyst or a base catalyst that promotes the hydrolysis and condensation reaction of the group P.
  • the content of the additive is preferably 10% by mass or less, and more preferably 1% by mass or less, based on the total mass of the present surface treatment agent.
  • the surface treatment agent of the present disclosure includes the compound of the present disclosure.
  • the surface treatment agent of the present disclosure may also include the compound of the present disclosure and a liquid medium.
  • the surface treatment agent of the present disclosure may also be the composition of the present disclosure.
  • the preferred embodiment of the liquid medium contained in the surface treatment agent is the same as the preferred embodiment of the liquid medium contained in the composition of the present disclosure.
  • the compound of the present disclosure contains an alkyl group having two or more carbon atoms, an organopolysiloxane group, and a group P. Therefore, by using a surface treatment agent containing the compound of the present disclosure, a surface treatment layer having excellent water repellency and abrasion resistance can be formed.
  • the surface treatment agent of the present disclosure may contain at least one of the compound represented by formula (1) and the compound represented by formula (2).
  • the surface treatment agent of the present disclosure may contain both the compound represented by formula (1) and the compound represented by formula (2).
  • the surface treatment agent disclosed herein is particularly suitable for use on optical components.
  • the article of the present disclosure includes a substrate and a surface treatment layer disposed on the substrate and surface-treated with the surface treatment agent of the present disclosure.
  • the surface treatment layer may be formed on a part of the surface of the substrate, or may be formed on the entire surface of the substrate.
  • the surface treatment layer may be spread on the surface of the substrate in the form of a film, or may be scattered in the form of dots.
  • the compound of the present disclosure is contained in a state in which the hydrolysis of part or all of the group P has progressed and the dehydration condensation reaction of the silanol groups has progressed.
  • the thickness of the surface treatment layer is preferably 1 to 100 nm, and more preferably 1 to 50 nm. If the thickness of the surface treatment layer is 1 nm or more, the effect of the surface treatment is likely to be sufficient. If the thickness of the surface treatment layer is 100 nm or less, the utilization efficiency is high.
  • the thickness of the surface treatment layer can be calculated from the vibration period of the interference pattern obtained by obtaining an interference pattern of reflected X-rays by X-ray reflectivity method using a thin film analysis X-ray diffractometer (product name "ATX-G", manufactured by RIGAKU Corporation).
  • the type of the substrate is not particularly limited, and may be, for example, a substrate that is required to be imparted with water repellency.
  • the substrate include a substrate that may be used by contacting with other articles (e.g., a stylus) or a person's finger; a substrate that may be held by a person's finger during operation; and a substrate that may be placed on top of other articles (e.g., a mounting table).
  • the material of the substrate include metal, resin, glass, sapphire, ceramic, semiconductor, stone, fiber, nonwoven fabric, paper, wood, fur, natural leather, artificial leather, ceramics, and composite materials thereof. Glass may be chemically strengthened.
  • the substrate may be a building material, a decorative building material, an interior item, a transport device (e.g., an automobile), a sign, a bulletin board, a drinking vessel, a tableware, an aquarium, an ornamental device (e.g., a frame, a box), a laboratory device, a furniture, a textile product, a packaging container; a glass or a resin used in art, sports, a game, etc.; a glass or a resin used in the exterior part (excluding the display part) of a device such as a mobile phone (e.g., a smartphone), a personal digital assistant, a game machine, a remote control, etc.
  • the shape of the substrate may be a plate or a film.
  • a substrate for a touch panel As the substrate, a substrate for a touch panel, a substrate for a display, or a lens for glasses is suitable, and a substrate for a touch panel is particularly suitable.
  • a substrate for a touch panel As the material for the substrate for a touch panel, glass or a transparent resin is preferred.
  • the substrate may be a substrate having one or both surfaces subjected to a surface treatment such as corona discharge treatment, plasma treatment, or plasma graft polymerization treatment.
  • a substrate having been subjected to a surface treatment has better adhesion to the surface treatment layer, and the abrasion resistance of the surface treatment layer is improved. For this reason, it is preferable to perform a surface treatment on the surface of the substrate that comes into contact with the surface treatment layer.
  • a base layer which will be described later, is provided on the substrate having been subjected to a surface treatment, the adhesion to the base layer is better, and the abrasion resistance of the surface treatment layer is improved. For this reason, when a base layer is provided, it is preferable to perform a surface treatment on the surface of the substrate that comes into contact with the base layer.
  • the surface treatment layer may be provided directly on the surface of the substrate, or a base layer may be provided between the substrate and the surface treatment layer. From the viewpoint of further improving the water repellency and abrasion resistance of the surface treatment layer, it is preferable that the article of the present disclosure includes a substrate, a base layer disposed on the substrate, and a surface treatment layer that is surface-treated with the surface treatment agent of the present disclosure and disposed on the base layer.
  • the underlayer is preferably a layer containing an oxide containing silicon and at least one specific element selected from the group consisting of Group 1 elements, Group 2 elements, Group 4 elements, Group 5 elements, Group 13 elements, and Group 15 elements of the periodic table.
  • Group 1 elements of the periodic table refer to lithium, sodium, potassium, rubidium, and cesium.
  • Group 1 elements lithium, sodium, and potassium are preferred, and sodium and potassium are more preferred, from the viewpoint of being able to form a surface treatment layer on the underlayer more uniformly without defects, or of further suppressing variation in the composition of the underlayer between samples.
  • the underlayer may contain two or more types of Group 1 elements.
  • Group 2 elements of the periodic table refer to beryllium, magnesium, calcium, strontium, and barium.
  • magnesium, calcium, and barium are preferred, and magnesium and calcium are more preferred, from the viewpoint of being able to form a surface treatment layer on the underlayer more uniformly without defects, or from the viewpoint of further suppressing variation in the composition of the underlayer between samples.
  • the underlayer may contain two or more types of Group 2 elements.
  • Group 4 elements of the periodic table refer to titanium, zirconium, and hafnium.
  • Group 4 elements titanium and zirconium are preferred, and titanium is more preferred, from the viewpoint of being able to form a surface treatment layer on the underlayer more uniformly without defects, or from the viewpoint of further suppressing variation in the composition of the underlayer between samples.
  • the underlayer may contain two or more types of Group 4 elements.
  • Group 5 elements of the periodic table refer to vanadium, niobium, and tantalum.
  • Group 5 element vanadium is particularly preferred from the viewpoint of providing a surface treatment layer with superior abrasion resistance.
  • the undercoat layer may contain two or more Group 5 elements.
  • Group 13 elements of the periodic table refer to boron, aluminum, gallium, and indium.
  • Group 13 elements boron, aluminum, and gallium are preferred, and boron and aluminum are more preferred, from the viewpoint of being able to form a surface treatment layer on the underlayer more uniformly without defects, or of further suppressing variation in the composition of the underlayer between samples.
  • the underlayer may contain two or more types of Group 13 elements.
  • the Group 15 elements of the periodic table (hereinafter also referred to as "Group 15 elements") refer to nitrogen, phosphorus, arsenic, antimony, and bismuth.
  • Group 15 elements from the viewpoint of being able to form a surface treatment layer on the underlayer more uniformly without defects, or from the viewpoint of further suppressing the variation in the composition of the underlayer between samples, phosphorus, antimony, and bismuth are preferred, and phosphorus and bismuth are more preferred.
  • the underlayer may contain two or more types of Group 15 elements.
  • Group 1 elements, Group 2 elements, and Group 13 elements are preferred because they provide a surface treatment layer with superior abrasion resistance, Group 1 elements and Group 2 elements are more preferred, and Group 1 elements are even more preferred.
  • the specific element may be one type of element or two or more types of elements.
  • the oxide contained in the underlayer may be a mixture of oxides of the above elements (silicon and the specific element) alone (for example, a mixture of silicon oxide and an oxide of the specific element), a composite oxide containing two or more of the above elements, or a mixture of an oxide of the above elements alone and a composite oxide.
  • the ratio of the total molar concentration of the specific elements in the underlayer to the molar concentration of silicon in the underlayer (specific elements/silicon) is preferably 0.02 to 2.90, more preferably 0.10 to 2.00, and even more preferably 0.20 to 1.80, from the viewpoint of achieving better abrasion resistance of the surface treatment layer.
  • the molar concentration (mol %) of each element in the underlayer can be measured, for example, by depth profile analysis using X-ray photoelectron spectroscopy (XPS) using ion sputtering.
  • the underlayer may be a single layer or multiple layers.
  • the underlayer may have an uneven surface.
  • the thickness of the underlayer is preferably 1 to 100 nm, more preferably 1 to 50 nm, and even more preferably 2 to 20 nm. If the thickness of the underlayer is equal to or greater than the lower limit, the adhesion of the underlayer to the surface treatment layer is improved, and the surface treatment layer has better abrasion resistance. If the thickness of the underlayer is equal to or less than the upper limit, the underlayer itself has better abrasion resistance. The thickness of the underlayer is measured by observing a cross section of the underlayer with a transmission electron microscope (TEM).
  • TEM transmission electron microscope
  • the undercoat layer can be formed, for example, by a deposition method using a deposition material or a wet coating method.
  • the deposition material used in the deposition method preferably contains an oxide containing silicon and a specific element.
  • Specific examples of the form of the deposition material include powder, melt, sintered body, granulated body, and crushed body, and from the viewpoint of handleability, the melt, sintered body, and granulated body are preferred.
  • the melt means a solid obtained by melting the powder of the deposition material at a high temperature and then cooling and solidifying it.
  • the sintered body means a solid obtained by firing the powder of the deposition material, and if necessary, a molded body may be used by pressing the powder instead of the powder of the deposition material.
  • the granulated body means a solid obtained by kneading the powder of the deposition material with a liquid medium (e.g., water, organic solvent) to obtain particles, and then drying the particles.
  • a liquid medium e.g., water, organic solvent
  • the deposition material can be produced, for example, by the following method.
  • a method of mixing a powder containing silicon e.g., powder made of silicon oxide, silica sand, silica gel
  • a powder containing a specific element e.g., powder of an oxide, carbonate, sulfate, nitrate, oxalate, hydroxide of a specific element
  • water e.g., water, drying the mixture, and then firing the dried mixture or a compact obtained by pressing the mixture to obtain a sintered body.
  • silicon e.g., powder made of silicon oxide, silica sand, silica gel
  • a specific element e.g., powder of an oxide, carbonate, sulfate, nitrate, oxalate, hydroxide of a specific element
  • a specific example of a deposition method using a deposition material is a vacuum deposition method, in which a deposition material is evaporated in a vacuum chamber and attached to the surface of a substrate.
  • the temperature during deposition (for example, the temperature of a boat in which a deposition material is placed when a vacuum deposition apparatus is used) is preferably 100 to 3,000°C, and more preferably 500 to 3,000°C.
  • the pressure during deposition (for example, the pressure inside a tank in which a deposition material is placed when a vacuum deposition apparatus is used) is preferably 1 Pa or less, and more preferably 0.1 Pa or less.
  • one deposition material may be used, or two or more deposition materials containing different elements may be used.
  • the evaporation method of 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 to melt and evaporate the surface.
  • the electron gun method is preferred as the evaporation method of the deposition material because it can evaporate high melting point substances because it can heat locally, and because the areas not hit by the electron beam are at low temperature, there is no risk of reaction with the container or contamination with impurities.
  • the evaporation method of the deposition materials may use multiple boats, or may use a single boat containing all the deposition materials.
  • the deposition method may be co-deposition or alternating deposition.
  • examples include a case where silica and a specific source are mixed in the same boat and used, a case where silica and a specific element source are placed in separate boats and co-deposited, and a case where they are placed in separate boats and alternately deposited.
  • the deposition conditions, order, etc. are appropriately selected depending on the configuration of the underlayer.
  • a base layer on a substrate it is preferable to form a base layer on a substrate by a wet coating method using a coating liquid that contains a silicon-containing compound, a compound containing a specific element, and a liquid medium.
  • silicon compounds include silicon oxide, silicic acid, partial condensates of silicic acid, alkoxysilanes, and partial hydrolysis condensates of alkoxysilanes.
  • Specific examples of compounds containing a specific element include oxides of a specific element, alkoxides of a specific element, carbonates of a specific element, sulfates of a specific element, nitrates of a specific element, oxalates of a specific element, and hydroxides of a specific element.
  • the liquid medium may be the same as the liquid medium contained in the composition of the present disclosure.
  • the content of the liquid medium is preferably from 0.01 to 20% by mass, and more preferably from 0.1 to 10% by mass, based on the total amount of the coating liquid used to form the underlayer.
  • wet coating methods for forming the underlayer include spin coating, wipe coating, spray coating, squeegee coating, dip coating, die coating, inkjet coating, flow coating, roll coating, casting, Langmuir-Blodgett coating, and gravure coating.
  • the drying temperature for the coating film is preferably 20 to 200°C, and more preferably 80 to 160°C.
  • the article of the present disclosure may be an optical material having a surface treatment layer as the outermost layer.
  • Preferred examples of the optical material include optical materials related to displays and the like, as well as a wide variety of other optical materials.
  • optical materials include displays such as cathode ray tubes (CRTs; for example, personal computer monitors), liquid crystal displays, plasma displays, organic EL displays, inorganic thin-film EL dot matrix displays, rear projection displays, fluorescent display tubes (VFDs), and field emission displays (FEDs; Field Emission Displays), or protective plates for such displays, or displays whose surfaces have been treated with an anti-reflection film.
  • the article of the present disclosure is preferably an optical member, such as a car navigation system, a mobile phone, a smartphone, a digital camera, a digital video camera, a PDA, a portable audio player, a car audio, a game machine, an eyeglass lens, a camera lens, a lens filter, sunglasses, a medical device such as a gastroscope, a copier, a PC, a display (e.g., a liquid crystal display, an organic electroluminescence display, a plasma display, a touch panel display), a touch panel, a protective film, and an anti-reflection film.
  • optical members examples include front protective plates, antireflection plates, polarizing plates, and antiglare plates for displays such as PDPs and LCDs; disc surfaces of optical discs such as Blu-ray (registered trademark) discs, DVD discs, CD-Rs, and MOs; optical fibers; and display surfaces of clocks.
  • the article of the present disclosure is preferably a display or a touch panel.
  • the article of the present disclosure may be a medical device or medical material.
  • the article of the present disclosure may also be an automobile interior or exterior component.
  • exterior materials include windows, light covers, and exterior camera covers.
  • interior materials include instrument panel covers, navigation system touch panels, and decorative interior materials.
  • the material constituting the surface of the substrate is a material for optical members, for example, glass or transparent plastic.
  • the surface (outermost layer) of the substrate may have a functional layer such as a hard coat layer or an antireflection layer formed thereon.
  • the antireflection layer may be either a single-layer antireflection layer or a multi-layer antireflection layer.
  • a transparent electrode for example, a thin film using indium tin oxide (ITO) or indium zinc oxide
  • ITO indium tin oxide
  • 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, a liquid crystal display module, etc., depending on the specific specifications, etc.
  • the method for producing an article according to the present disclosure is, for example, a method for producing an article having a surface treatment layer formed on a substrate by performing a surface treatment on a substrate using the surface treatment agent according to the present disclosure.
  • Examples of the surface treatment include a dry coating method and a wet coating method.
  • Dry coating methods include vacuum deposition, CVD, sputtering, and the like.
  • vacuum deposition is preferred from the viewpoint of suppressing decomposition of the compound and the simplicity of the device.
  • a pellet-shaped material in which a metal porous body such as iron or steel is impregnated with the compound of the present disclosure may be used.
  • a composition containing the compound of the present disclosure and a liquid medium may be impregnated into a metal porous body such as iron or steel, the liquid medium may be dried, and a pellet-shaped material impregnated with the compound of the present disclosure may be used.
  • Wet coating methods include, for example, 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.
  • an operation for promoting the reaction between the compound of the present disclosure and the substrate may be carried out.
  • Such an operation may include heating, humidification, light irradiation, etc.
  • by heating a substrate on which a surface treatment layer has been formed in an atmosphere containing moisture it is possible to promote reactions such as hydrolysis reaction of hydrolyzable groups, reaction between hydroxyl groups or the like on the substrate surface and silanol groups, and generation of siloxane bonds through condensation reaction of silanol groups.
  • compounds in the surface treatment layer that are not chemically bonded to other compounds or the substrate may be removed as necessary. Examples of the method for removing the compounds include pouring a solvent onto the surface treatment layer and wiping the compounds off with a cloth soaked in the solvent.
  • Examples 1 and 2 are comparative examples, and Examples 3 to 7 are working examples.
  • Substrates were surface-treated using compound (12), compound (14), compound (16), compound (17), compound (19), compound (21), and compound (23) by the following method to obtain articles of Examples 1 to 7.
  • a dry coating method was used as the surface treatment method.
  • 30 g of silicon oxide was placed as a deposition source in a copper hearth in a vacuum deposition apparatus (VTR-350M manufactured by ULVAC KIKOU CO., LTD.).
  • a glass substrate was placed in the vacuum deposition apparatus, and the inside of the vacuum deposition apparatus was evacuated to a pressure of 5 ⁇ 10 ⁇ 3 Pa or less.
  • the hearth was heated to about 2,000° C., and silicon oxide was vacuum-deposited on the surface of the substrate, producing a substrate with a silicon oxide layer having a thickness of about 20 nm.
  • 0.5 g of each compound was loaded into a molybdenum boat in a vacuum deposition apparatus (ULVAC, VTR350M), and the inside of the vacuum deposition apparatus was evacuated to 1 ⁇ 10 ⁇ 3 Pa or less.
  • the boat in which the compound was placed was heated at a temperature increase 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, a shutter was opened to start film formation on the surface of the silicon oxide layer side of the substrate.
  • the shutter was closed to terminate the film formation on the surface of the substrate.
  • the substrate on which the compound was deposited was heat-treated at 200° C. for 30 minutes and washed with AC-2000 (manufactured by AGC Corporation), to obtain evaluation samples (articles) of Examples 1 to 4 in which the substrate, silicon oxide layer, and surface treatment layer were laminated in this order.
  • ⁇ Abrasion resistance (steel wool)> For the surface treatment layer, a reciprocating traverse tester (manufactured by KNT Co., Ltd.) was used in accordance with JIS L0849:2013 (ISO 105-X12:2001) to measure the water contact angle after reciprocating steel wool Bonstar (#0000) 10,000 times at a pressure of 98.07 kPa and a speed of 320 cm/min.
  • the method for measuring the water contact angle after friction was the same as the method for measuring the initial water contact angle in the evaluation method for water repellency.
  • the smaller the decrease in water repellency (water contact angle) after friction the smaller the decrease in performance due to friction and the more excellent the abrasion resistance.
  • ⁇ Fingerprint removal ability> A 1 kg weight with a red rubber plug with a diameter of 2 cm was prepared as the fingerprint stamp part. Next, 70 ⁇ L of artificial fingerprint liquid (manufactured by Isekyu Co., Ltd.) was dropped onto the rag, and the fingerprint stamp was attached to the artificial fingerprint liquid for 1 minute. In order to remove the artificial fingerprint liquid that was excessively attached to the fingerprint stamp, the fingerprint stamp was attached to a new rag for 20 seconds. Then, the article on which the surface treatment layer was formed was placed on a hot plate whose temperature was adjusted to 23°C. The fingerprint stamp was stamped on the surface treatment layer.
  • artificial fingerprint liquid manufactured by Isekyu Co., Ltd.
  • the article on which the artificial fingerprint liquid was attached was placed on a sliding device (product name "HHS-2000", manufactured by Shinto Scientific Co., Ltd.).
  • a wiping cloth (Savina Minimax manufactured by KB Seiren Co., Ltd.) was attached to a flat indenter having an area of 1 cm square using double-sided tape, and the item was placed on the sliding device.
  • the artificial fingerprint liquid attached to the surface treatment layer was wiped off with a wiping cloth in one direction with a load of 100 g.
  • the haze of the wiped area was measured using a haze meter (product name "NDH7000SP", manufactured by Nippon Denshoku Co., Ltd.)
  • the evaluation criteria were as follows. The results are shown in Table 1.
  • C Haze value is 1% or more
  • the surface treatment layer was irradiated with light (650 W/m 2 , 300-700 nm) for 500 hours at a black panel temperature of 63°C using a tabletop xenon arc lamp accelerated light resistance tester (SUNTEST XLS+: product name, manufactured by Toyo Seiki Co., Ltd.), and then the water contact angle of the surface treatment layer was measured using the method described above.
  • the evaluation criteria are as follows. The results are shown in Table 1.
  • Decrease in water contact angle (initial water contact angle) - (water contact angle after accelerated light resistance test)
  • the compounds disclosed herein are useful as surface treatment agents.
  • the surface treatment agent can be used, for example, for display devices such as touch panel displays, optical elements, semiconductor elements, building materials, automobile parts, and substrates in nanoimprint technology.
  • the surface treatment agent can also be used for bodies, window glass (front glass, side glass, rear glass), mirrors, bumpers, and the like in transport devices such as trains, automobiles, ships, and aircraft.
  • the surface treatment agent can also be used for outdoor items such as building exterior walls, tents, solar power generation modules, soundproofing boards, and concrete; fishing nets, insect nets, and aquariums.
  • the surface treatment agent can also be used for various indoor equipment such as kitchens, bathrooms, washstands, mirrors, and toilet peripheral parts; ceramics such as chandeliers and tiles; and artificial marble and air conditioners.
  • the surface treatment agent can also be used as an anti-fouling treatment for jigs, inner walls, piping, and the like in factories.
  • the surface treatment agent can also be used for goggles, glasses, helmets, pachinko machines, fibers, umbrellas, playground equipment, and soccer balls.
  • the surface treatment agent can also be used as an anti-adhesion agent for various packaging materials such as food packaging materials, cosmetic packaging materials, the inside of pots, etc.
  • the surface treatment agent can also be used for car navigation systems, mobile phones, smartphones, digital cameras, digital video cameras, PDAs, portable audio players, car audio, game machines, eyeglass lenses, camera lenses, lens filters, sunglasses, medical equipment such as gastroscopes, copiers, PCs, displays (e.g., liquid crystal displays, organic EL displays, plasma displays, touch panel displays), touch panels, protective films, anti-reflection films, and other optical components.
  • displays e.g., liquid crystal displays, organic EL displays, plasma displays, touch panel displays), touch panels, protective films, anti-reflection films, and other optical components.

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Abstract

La présente invention concerne : un nouveau composé qui permet de former une couche de traitement de surface présentant une excellente résistance à l'usure ; et analogue.　Un composé selon la présente invention contient le groupe P décrit ci-dessous et une chaîne fluoropolyéther. Groupe P : -[Si(R1)2-X]n1-Si(R1)3. Chaque X représente indépendamment un atome d'oxygène ou un atome de carbone, chaque R1 représente indépendamment un groupe hydrolysable, un groupe ayant un groupe hydrolysable, un groupe hydroxyle, ou un groupe hydrocarboné, au moins quatre des R1 parmi les R1 représentent des groupes hydrolysables, des groupes ayant des groupes hydrolysables, ou des groupes hydroxyle, et n1 représente un nombre entier de 1 à 3.
PCT/JP2024/033866 2023-09-27 2024-09-24 Composé, composition, agent de traitement de surface, article et procédé de production d'article Pending WO2025070362A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0436286A (ja) * 1990-05-29 1992-02-06 Shin Etsu Chem Co Ltd アルコキシハイドロジェンシロキサン化合物及びその製造方法
JP2014218639A (ja) * 2012-11-05 2014-11-20 ダイキン工業株式会社 パーフルオロ（ポリ）エーテル基含有シラン化合物
WO2021010105A1 (fr) * 2019-07-17 2021-01-21 ダイキン工業株式会社 Agent de traitement de surface
JP2022036343A (ja) * 2018-10-16 2022-03-08 Ａｇｃ株式会社 含フッ素エーテル化合物および物品

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0436286A (ja) * 1990-05-29 1992-02-06 Shin Etsu Chem Co Ltd アルコキシハイドロジェンシロキサン化合物及びその製造方法
JP2014218639A (ja) * 2012-11-05 2014-11-20 ダイキン工業株式会社 パーフルオロ（ポリ）エーテル基含有シラン化合物
JP2022036343A (ja) * 2018-10-16 2022-03-08 Ａｇｃ株式会社 含フッ素エーテル化合物および物品
WO2021010105A1 (fr) * 2019-07-17 2021-01-21 ダイキン工業株式会社 Agent de traitement de surface

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