WO2023210470A1 - Composé, composition, agent de traitement de surface, procédé de production d'article et article - Google Patents

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

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WO2023210470A1
WO2023210470A1 PCT/JP2023/015681 JP2023015681W WO2023210470A1 WO 2023210470 A1 WO2023210470 A1 WO 2023210470A1 JP 2023015681 W JP2023015681 W JP 2023015681W WO 2023210470 A1 WO2023210470 A1 WO 2023210470A1
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group
compound
surface treatment
carbon atoms
article
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PCT/JP2023/015681
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Japanese (ja)
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亮平 小口
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Ａｇｃ株式会社
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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

Definitions

  • the present disclosure relates to compounds, compositions, surface treatment agents, methods of manufacturing articles, and articles.
  • Patent Document 1 a cured film containing a specific organosilicone compound as a matrix resin is provided on the outermost surface of a base material, and the two-dimensional surface roughness when a fingerprint is attached to the cured film is set in a specific range.
  • a substrate with a cured coating is described.
  • Patent Document 2 describes a fingerprint-resistant transparent substrate having a lipophilic coating containing a compound in which a specific monool or polyol and a silicon compound are bonded.
  • compositions used as surface treatment agents and the like are required to have abrasion resistance in addition to the property of reducing the visibility of fingerprints in the surface treatment layer formed.
  • the present disclosure has been made in view of these circumstances, and the problem to be solved by an embodiment of the present invention is to provide a base material with properties that reduce fingerprint visibility and abrasion resistance.
  • An object of the present invention is to provide novel compounds and compositions useful as surface treatment agents capable of forming surface treatment layers.
  • the problem to be solved by an embodiment of the present invention is to provide a surface treatment agent that can form a surface treatment layer on a base material that has both characteristics of reducing fingerprint visibility and wear resistance. be.
  • the problem to be solved by one embodiment of the present invention is to provide an article having a surface treatment layer that has both characteristics of reducing fingerprint visibility and wear resistance, and a method for manufacturing the same.
  • the present disclosure includes the following aspects.
  • ⁇ 1> A compound having a reactive silyl group, an ethylene oxide unit, an alkylene oxide unit having 3 to 6 carbon atoms, and a hydroxy group bonded to a carbon atom,
  • the ratio of Ma to the total of Ma and Mb is Ma/(Ma+Mb)
  • ⁇ 3> A compound represented by the following formula (1).
  • R 2 is each independently an alkylene group having 3 to 6 carbon atoms
  • Q 1 is a (d+e)-valent linking group
  • Y 1 is a (g+1)-valent linking group
  • R 1 is each independently a monovalent hydrocarbon group
  • L 2 is each independently a hydrolyzable group or a hydroxyl group
  • a1, a2, b1, and b2 are each independently an integer of 1 to 300
  • d and e are each independently an integer of 1 to 10
  • n is an integer from 0 to 2
  • g is an integer greater than or equal to 1
  • (OCH 2 CH 2 ) b1 (OR 2 ) a1 is such that (OCH 2 CH 2 ) and (OR 2 ) may be combined in any order, and when at least one of a1 and b1 is 2 or more, It can be combined randomly or in blocks, (R 2 O) a2 (CH 2 CH 2 O) b2 , (R 2 O) and (CH 2 CH 2 O
  • the value is between 0.2 and 0.8.
  • ⁇ 4> The compound according to ⁇ 3>, wherein g in the formula (1) is 2 or more.
  • ⁇ 5> A composition comprising the compound according to any one of ⁇ 1> to ⁇ 4> and a liquid medium.
  • ⁇ 6> A surface treatment agent comprising the compound according to any one of ⁇ 1> to ⁇ 4>.
  • ⁇ 7> The surface treatment agent according to ⁇ 6>, further comprising a liquid medium.
  • a method for manufacturing an article comprising performing a surface treatment on a base material using the surface treatment agent described in ⁇ 6> or ⁇ 7>, and manufacturing an article in which a surface treatment layer is formed on the base material. .
  • novel compounds and compositions useful as surface treatment agents capable of forming a surface treatment layer on a substrate that has both characteristics of reducing fingerprint visibility and wear resistance is provided.
  • a surface treatment agent is provided that can form a surface treatment layer on a base material that has both characteristics of reducing fingerprint visibility and wear resistance.
  • an article and a method for manufacturing the article are provided, which have a surface treatment layer that has both properties that reduce fingerprint visibility and wear resistance.
  • numerical ranges indicated using “ ⁇ ” include the numerical values written before and after " ⁇ " as minimum and maximum values, respectively.
  • each component may contain multiple types of corresponding substances. If there are multiple types of substances corresponding to each component in the composition, the content rate or content of each component is the total content rate or content of the multiple types of substances present in the composition, unless otherwise specified. means quantity.
  • the upper limit or lower limit described in one numerical range may be replaced with the upper limit or lower limit of another numerical range described step by step.
  • the upper limit or lower limit of the numerical range may be replaced with the values shown in the Examples.
  • the term “layer” or “film” refers to the case where the layer or film is formed only in a part of the region, in addition to the case where the layer or film is formed in the entire region when observing the region where the layer or film is present. This also includes cases where it is formed.
  • the term “surface treated layer” refers to a layer formed on the surface of a base material by surface treatment.
  • the compound or group represented by the formula (X) may be referred to as a compound (X) or a group (X), respectively.
  • the compound of the present disclosure has a reactive silyl group, an ethylene oxide unit, an alkylene oxide unit having 3 to 6 carbon atoms, and a hydroxy group bonded to a carbon atom, and the carbon atoms contained in the compound of the present disclosure have a
  • the number of moles of alkylene oxide units of numbers 3 to 6 is Ma
  • the number of moles of the ethylene oxide unit is Mb
  • the value of the ratio Ma/(Ma+Mb) to the total of Ma and Mb is 0.2 to 0. It is .8.
  • ethylene oxide units i.e.
  • EO units alkylene oxide units with 3 to 6 carbon atoms
  • R 2 O alkylene oxide units with 3 to 6 carbon atoms
  • the alkylene group) is also referred to as the "RO unit”.
  • the compound of the present disclosure has a reactive silyl group that has high adhesion to the substrate, and thus can form a surface treatment layer that adheres to the surface of the substrate. Since the compound of the present disclosure has an EO unit and a hydroxy group bonded to a carbon atom, it can have particularly high hydrophilicity compared to a compound in which all hydroxy groups are silylated. Therefore, a highly hydrophilic surface treatment layer can be formed, and even if fingerprint stains adhere to the surface of the surface treatment layer, the adhered fingerprint stains will easily spread and become difficult to form into droplets. Further, since diffuse reflection of light due to fingerprint stains is less likely to occur, fingerprint stains are less noticeable, and the surface treatment layer has a good property of reducing fingerprint visibility.
  • the compounds of the present disclosure have not only EO units but also RO units and have a value of Ma/(Ma+Mb) of 0.2 to 0.8. Therefore, the compound of the present disclosure can form a surface treatment layer with higher abrasion resistance than, for example, a compound without an RO unit, and can achieve both the property of reducing fingerprint visibility and the abrasion resistance in the surface treatment layer. It is believed that this can be achieved.
  • the compounds of the present disclosure have a polyalkylene oxide chain composed of one or more EO units and one or more RO units.
  • a polyalkylene oxide chain composed of one or more EO units and one or more RO units will also be referred to as a "specific polyalkylene oxide chain.”
  • the compound of the present disclosure has a partial structure D in which an oxygen atom at one end of a specific polyalkylene oxide chain is bonded to a reactive silyl group via a single bond or a linking group Y1 , and a partial structure D in which an oxygen atom at one end of a specific polyalkylene oxide chain is It is preferable to have a partial structure E bonded to a hydrogen atom.
  • partial structure D when the specific alkylene oxide chain is bonded to the reactive silyl group via a linking group, the linking group between the specific alkylene oxide chain and the reactive silyl group is a group that does not impair the purpose of the present disclosure. Any linking group may be used, and examples thereof include a linking group explained as Y 1 in formula (1) below.
  • the hydroxy group formed by bonding the oxygen atom at one end of the specific polyalkylene oxide chain to a hydrogen atom becomes the above-mentioned "hydroxy group bonded to a carbon atom.”
  • one or more partial structures D and one or more partial structures E are bonded via a linking group Q.
  • the carbon atom at the other end of the specific alkylene oxide chain in partial structure D and the carbon atom at the other end of the specific alkylene oxide chain in partial structure E are connected via a linking group Q.
  • the linking group may be any group that does not impair the purpose of the present disclosure, and examples thereof include the linking group explained as Q 1 in formula (1) below.
  • the compound of the present disclosure may have only one partial structure D in one molecule, or may have two or more partial structures D.
  • the number d of partial structures D that the compound of the present disclosure has in one molecule is, for example, 1 to 10, preferably 1 to 6, and more preferably 1 to 3 from the viewpoint of material availability.
  • the compound of the present disclosure may have only one partial structure E in one molecule, or may have two or more partial structures E.
  • the number e of partial structures E that the compound of the present disclosure has in one molecule is, for example, from 1 to 10, preferably from 1 to 6, and more preferably from 1 to 3 from the viewpoint of material availability.
  • the total number (d+e) of partial structures D and partial structures E that the compound of the present disclosure has in one molecule is, for example, 2 to 20, preferably 2 to 20 from the viewpoint of material availability, and 2 to 20. 6 is more preferred.
  • the ratio of e to the sum of d and e is e. /(d+e) is preferably 0.05 to 0.9, more preferably 0.25 to 0.75, from the viewpoint of achieving both the property of reducing fingerprint visibility in the surface treatment layer and the abrasion resistance.
  • the compound of the present disclosure may have only one reactive silyl group in one molecule, or may have two or more reactive silyl groups.
  • the compound of the present disclosure preferably has two or more reactive silyl groups in one molecule from the viewpoint of improving wear resistance in the surface treatment layer.
  • the number of reactive silyl groups that the compound of the present disclosure has in one molecule is 1 or more, and from the viewpoint of further improving the abrasion resistance of the surface treatment layer, it is preferably 1 to 18, more preferably 2 to 12, 2 to 8 are more preferred.
  • the number of reactive silyl groups that the compound of the present disclosure has may be one.
  • the compound of the present disclosure has two or more reactive silyl groups attached to the oxygen atom at one end of one specific polyalkylene oxide chain via a trivalent or higher valent linking group, from the viewpoint of improving wear resistance in the surface treatment layer. Preferably, they are bonded.
  • the compound of the present disclosure has a partial structure D
  • one partial structure D has two or more reactive silyl groups.
  • the number g of reactive silyl groups that one partial structure D has is 1 or more, preferably 1 to 3, more preferably 2 to 3, from the viewpoint of improving wear resistance in the surface treatment layer.
  • the number of hydroxy groups bonded to carbon atoms that the compound of the present disclosure has in one molecule is 1 or more, and preferably 1 to 10 from the viewpoint of improving the property of reducing fingerprint visibility in the surface treatment layer. 1 to 6 are more preferred, and 1 to 3 are even more preferred.
  • the ratio of e to the sum of f and e. e/(f+e) is preferably 0.17 to 0.83, more preferably 0.33 to 0.67, from the viewpoint of achieving both the property of reducing fingerprint visibility in the surface treatment layer and the abrasion resistance.
  • the number f of reactive silyl groups in one molecule is the product of the number g of reactive silyl groups in one partial structure D and the number d of partial structures D in one molecule (g ⁇ d). corresponds to
  • Reactive silyl group Compounds of the present disclosure contain reactive silyl groups.
  • the reactive silyl group is located at the end of the compound.
  • a reactive silyl group means a group in which a reactive group is bonded to a Si atom.
  • the reactive group is preferably a hydrolyzable group or a hydroxyl group.
  • a hydrolyzable group is a group that becomes a hydroxyl group through a hydrolysis reaction. That is, the hydrolyzable silyl group represented by Si-L becomes a silanol group represented by Si-OH through a hydrolysis reaction.
  • the silanol groups further react among themselves to form Si--O--Si bonds.
  • the silanol group can undergo a dehydration condensation reaction with a silanol group derived from an oxide present on the surface of the base material to form a Si--O--Si bond.
  • the hydrolyzable group include an alkoxy group, an aryloxy group, a halogen atom, an acyl group, an acyloxy group, and an isocyanato group (-NCO).
  • the alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms.
  • the aryl group of the aryloxy group includes a heteroaryl group.
  • the halogen atom is preferably a chlorine atom.
  • the acyl group is preferably an acyl group having 1 to 6 carbon atoms.
  • the acyloxy group is preferably an acyloxy group having 1 to 6 carbon atoms.
  • the reactive silyl group is preferably an alkoxysilyl group or a trichlorosilyl group.
  • the reactive silyl group is more preferably an alkoxysilyl group.
  • the alkoxysilyl group is preferably a dialkoxysilyl group or a trialkoxysilyl group, and more preferably a trialkoxysilyl group.
  • R 1 is each independently a monovalent hydrocarbon group
  • L 2 is each independently a hydrolyzable group or a hydroxyl group
  • n is an integer of 0 to 2.
  • the multiple reactive silyl groups may be the same or different from each other. From the viewpoint of easy availability of raw materials and ease of manufacturing the compound, it is preferable that the plurality of reactive silyl groups are the same.
  • Each R 1 is independently a monovalent hydrocarbon group, and a monovalent saturated hydrocarbon group is preferable.
  • the number of carbon atoms in R 1 is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2.
  • Each L 2 is independently a hydrolyzable group or a hydroxyl group.
  • hydrolyzable group those mentioned above are preferred.
  • L 2 is preferably an alkoxy group or a halogen atom, more preferably an alkoxy group having 1 to 4 carbon atoms or a halogen atom, from the viewpoint of ease of manufacturing the compound.
  • L 2 is preferably an alkoxy group having 1 to 4 carbon atoms, from the viewpoint of less outgassing during coating and better storage stability of the compound.
  • L 2 is more preferably an ethoxy group.
  • L 2 is more preferably a methoxy group.
  • at least one of L 2 is preferably the above group, and more preferably all of L 2 are the above groups.
  • n is an integer of 0 to 2, preferably 0 or 1, and more preferably 0.
  • the presence of a plurality of L 2 makes the adhesion of the surface treatment layer to the base material stronger.
  • n is 1 or less, the plurality of L2s present in one molecule may be the same or different from each other. From the viewpoint of easy availability of raw materials and ease of manufacturing the compound, it is preferable that the plurality of L 2 's are the same.
  • n is 2
  • multiple R 1s present in one molecule may be the same or different from each other. From the viewpoint of easy availability of raw materials and ease of manufacturing the compound, it is preferable that a plurality of R 1 's are the same.
  • hydroxy group bonded to carbon atom examples include a hydroxy group formed by bonding an oxygen atom at one end of a specific polyalkylene oxide chain described below with a hydrogen atom.
  • a hydroxy group formed by bonding an oxygen atom at one end of a specific polyalkylene oxide chain with a hydrogen atom is also referred to as a "specific hydroxy group.”
  • the hydroxy group bonded to the carbon atom may be a hydroxy group other than the specific hydroxy group.
  • Examples of compounds having a hydroxy group other than the specific hydroxy group include compounds having a linking group containing a hydroxy group bonded to a carbon atom as a linking group such as the above-mentioned linking group Y 1 and linking group Q.
  • the compound of the present disclosure preferably has at least a specific hydroxy group as a hydroxy group bonded to a carbon atom, from the viewpoint of reducing fingerprint visibility in the surface treatment layer.
  • the compounds of the present disclosure include ethylene oxide units (ie, EO units) and alkylene oxide units having 3 to 6 carbon atoms (ie, RO units).
  • EO units ethylene oxide units
  • RO units alkylene oxide units having 3 to 6 carbon atoms
  • the compounds of the present disclosure have a specific polyalkylene oxide chain composed of one or more EO units and one or more RO units.
  • the specific polyalkylene oxide chain is represented by the following formula (A). -(R 2 O) a (CH 2 CH 2 O) b -...(A)
  • R 2 is each independently an alkylene group having 3 to 6 carbon atoms
  • a and b are each independently an integer of 1 to 300
  • (R 2 O) and (CH 2 CH 2 O) may be combined in any order, and may be combined randomly or in blocks when at least one of a and b is 2 or more.
  • the number of carbon atoms in the alkylene group represented by R 2 in formula (A) is 3 to 6, preferably 3 to 5, more preferably 3 to 4, from the viewpoint of improving the abrasion resistance of the surface treatment layer. 3 is more preferred.
  • the alkylene group may be linear, branched, or cyclic, and among these, from the viewpoint of excellent wear resistance, linear or branched is preferable, and branched is more preferable.
  • alkylene group examples include n-propylene group, isopropylene group, n-butylene group, isobutylene group, cyclobutanediyl group, n-pentylene group, isopentylene group, sec-pentylene group, cyclopentanediyl group, n-hexylene group, Examples include isohexylene group, sec-hexylene group, and cyclohexanediyl group.
  • (R 2 O) examples include -C 3 H 6 O-, -C 4 H 8 O-, -C 5 H 10 O-, -C 6 H 12 O-, -CH(CH 3 )CH 2 O-, -CH(CH 3 )CH 2 CH 2 O-, -cycloC 4 H 6 -O-, -cycloC 5 H 8 -O, and -cycloC 6 H 10 -O-.
  • -cycloC 4 H 6 - means a cyclobutanediyl group.
  • the cyclobutanediyl group include a cyclobutane-1,2-diyl group and a cyclobutane-1,3-diyl group.
  • -cycloC 5 H 8 - means a cyclopentanediyl group.
  • the cyclopentanediyl group include a cyclopentane-1,2-diyl group and a cyclopentane-1,3-diyl group.
  • -cycloC 6 H 10 - means a cyclohexanediyl group.
  • the cyclohexanediyl group include a cyclohexane-1,2-diyl group, a cyclohexane-1,3-diyl group, and a cyclohexane-1,4-diyl group.
  • the number a of RO units contained in one specific polyalkylene oxide chain is an integer of 1 to 300, preferably an integer of 2 to 300 from the viewpoint of wear resistance of the surface treatment layer, and an integer of 2 to 100. More preferably, an integer of 2 to 50 is even more preferable.
  • the number b of EO units contained in one specific polyalkylene oxide chain is an integer of 1 to 300, preferably an integer of 2 to 300 from the viewpoint of the property of reducing fingerprint visibility in the surface treatment layer, and 2 to 300. An integer of 50 is more preferred, and an integer of 2 to 20 is even more preferred.
  • the total a+b of the number a of RO units and the number b of EO units contained in one specific polyalkylene oxide chain is an integer of 2 to 600, and the property of reducing fingerprint visibility and abrasion resistance are both compatible. From the viewpoint of feasibility, an integer of 4 to 600 is preferable, an integer of 4 to 150 is more preferable, and an integer of 4 to 70 is even more preferable.
  • the ratio a/(a+b) of the number a of RO units to the sum of the number a of RO units and the number b of EO units contained in one specific polyalkylene oxide chain is a characteristic that reduces the fingerprint visibility of the surface treatment layer. From the viewpoint of achieving both wear resistance and abrasion resistance, the range is preferably 0.2 to 0.8, more preferably 0.3 to 0.8, and even more preferably 0.3 to 0.7.
  • the number Sa of RO units that the compound of the present disclosure has in one molecule is preferably an integer of 2 to 50, more preferably an integer of 4 to 30, from the viewpoint of wear resistance of the surface treatment layer.
  • the number Sb of EO units that the compound of the present disclosure has in one molecule is preferably an integer of 2 to 50, more preferably an integer of 4 to 30, from the viewpoint of the property of reducing fingerprint visibility in the surface treatment layer.
  • the ratio Sa/(Sa+Sb) of Sa to the sum of the number Sa of RO units and the number Sb of EO units that the compound of the present disclosure has in one molecule, that is, the value of Ma/(Ma+Mb) is 0. .2 to 0.8, preferably 0.3 to 0.8, more preferably 0.3 to 0.7 from the viewpoint of achieving both the property of reducing fingerprint visibility in the surface treatment layer and the abrasion resistance. preferable.
  • the specific polyalkylene oxide chain may contain only one type of RO unit, or may contain two or more types of RO units, and preferably contains only one type of RO unit from the viewpoint of ease of synthesis.
  • the bonding order of the two or more types of RO units is not limited, and may be arranged randomly, alternately, or in blocks.
  • Containing two or more types of RO units means that two or more types of RO units with different numbers of carbon atoms exist in a specific polyalkylene oxide chain, and even if the number of carbon atoms is the same, the presence or absence of a side chain or the side chain This refers to the presence of two or more types of RO units with different types (for example, number of side chains, number of carbon atoms in the side chain, etc.).
  • the bonding order of the EO units and RO units contained in the specific polyalkylene oxide chain is not limited, and may be arranged randomly, alternately, or in blocks.
  • the bonding order of the EO units and RO units contained in the specific polyalkylene oxide chain is preferably block from the viewpoint of ease of synthesis and functional separation.
  • Examples of the structure of a specific polyalkylene oxide chain in which EO units and RO units are arranged in blocks include the following structures. -(R 2 O) a -(CH 2 CH 2 O) b - -(CH 2 CH 2 O) b - (R 2 O) a - -(R 2 O) a11 -(CH 2 CH 2 O) b -(R 2 O) a12 - -(CH 2 CH 2 O) b11 -(R 2 O) a -(CH 2 CH 2 O) b12 - -(R 2 O) a11 -(CH 2 CH 2 O) b11 -(R 2 O) a12 -(CH 2 CH 2 O) b12 - -(CH 2 CH 2 O) b11 -(R 2 O) a11 -(CH 2 CH 2 O) b12 - -(CH 2 CH 2 O) b11 -(R 2 O) a11 -(CH 2 CH
  • the structure represented by "-(R 2 O) a -" means a block in which a number of RO units are consecutively bonded.
  • the oxygen atom at the right end of the above formula is bonded to the reactive silyl group via a single bond or linking group Y1 , and the above formula
  • the oxygen atom at the right end of the above formula combines with a hydrogen atom to form a hydroxy group.
  • the compound of the present disclosure is preferably a compound represented by the following formula (1) from the viewpoint of forming a surface treatment layer that has both the property of reducing fingerprint visibility and abrasion resistance.
  • R 2 is each independently an alkylene group having 3 to 6 carbon atoms
  • Q 1 is a (d+e)-valent linking group
  • Y 1 is a (g+1)-valent linking group
  • R 1 is each independently a monovalent hydrocarbon group
  • L 2 is each independently a hydrolyzable group or a hydroxyl group
  • a1, a2, b1, and b2 are each independently an integer of 1 to 300
  • d and e are each independently an integer of 1 to 10
  • n is an integer from 0 to 2
  • g is an integer greater than or equal to 1
  • (OCH 2 CH 2 ) b1 (OR 2 ) a1 is such that (OCH 2 CH 2 ) and (OR 2 ) may be combined in any order, and when at least one of a1 and b1 is 2 or more, It can be combined randomly or in blocks, (R 2 O) a2 (CH 2 CH 2 O) b2 , (R 2 O) and (CH 2 CH 2 O
  • R 2 in formula (1) is the same as R 2 in formula (A), and multiple R 2 included in formula (1) may be the same or different from each other.
  • d and e in formula (1) are the same as the number of partial structures D in one molecule and the number of partial structures E in one molecule, respectively, which are described above.
  • the (d+e) specific polyalkylene oxide chains contained in the compound represented by formula (1) may be the same or different from each other.
  • R 1 , L 2 , and n in formula (1) are the same as R 1 , L, and n in formula (2) described above as the reactive silyl group.
  • the value of the ratio Sa/(Sa+Sb) is the same as the value of the ratio Ma/(Ma+Mb) described above.
  • Q 1 in formula (1) is a (d+e)-valent linking group.
  • the linking group represented by Q 1 includes an alkylene group, an arylene group, a carbonyl group, an ether bond, a thioether bond, a sulfonyl group, -NR 4 -, -N ⁇ , -SiR 4 2 -, >SiR 4 -, > Examples include Si ⁇ , polyhydric alcohol residues, polyhydric phenol residues, polyamine residues, and combinations thereof.
  • R 4 is a hydrogen atom or a hydrocarbon group.
  • the above-mentioned alkylene group may be linear, branched, or cyclic, and among these, linear or branched is preferable, and branched is more preferable.
  • the number of carbon atoms in the alkylene group is, for example, 2 to 10, preferably 2 to 8, and more preferably 2 to 6.
  • the hydrocarbon group represented by R 4 includes, for example, an aliphatic hydrocarbon group and an aromatic hydrocarbon group, with an aliphatic hydrocarbon group being preferred, an alkyl group being more preferred, and a methyl group being even more preferred.
  • the above arylene group is a group obtained by removing two hydrogen atoms from an aromatic ring. Examples of aromatic rings include benzene ring, naphthalene ring, fluorene ring, anthracene ring, furan ring, thiophene ring, and pyridine ring.
  • the linking group represented by Q1 is preferably a polyhydric alcohol residue, a polyhydric phenol residue, or a polyamine residue, more preferably a polyhydric alcohol residue or a polyamine residue, and a polyhydric alcohol residue. is even more preferable.
  • the linking group represented by Q 1 is preferably a polyhydric alcohol residue represented by the following formula (Q1-1) or a polyamine residue represented by the following formula (Q1-2).
  • Q 11 and Q 12 are each independently a (d+e)-valent linking group
  • E * is a bond bonding to partial structure E in formula (1)
  • * D is formula (1) This is a bonding portion that connects to the partial structure D inside.
  • the linking group represented by Q 11 or Q 12 includes an alkylene group, an arylene group, an ether bond, -NR 4 -, a combination thereof, and the like. R 4 is as described above.
  • the polyhydric alcohol residue refers to a group obtained by removing hydrogen atoms from all hydroxyl groups contained in a polyhydric alcohol.
  • a glycerin residue is represented by -OCH 2 -CH(-O-)-CH 2 O-.
  • the polyhydric alcohol may be a monomer or a polymer.
  • the monomer polyhydric alcohols include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, 1 , 4-cyclohexanediol, neopentyl glycol, diethanolamine, and other diols; trihydric or higher alcohols such as glycerin, diglycerin, trimethylolpropane, pentaerythritol, dipentaerythritol, tripentaerythritol, and hexitol; glucose, sorbitol, dextrose, Saccharides or derivatives thereof such as fructose, sucrose, methyl glucoside, trehalose; hydroxyl group-containing compounds such as fatty acid triglycerides or condensates thereof having hydroxyl groups such as castor
  • polyhydric alcohols that are polymers include polyethylene glycol, polypropylene glycol, polyoxytetramethylene glycol, polycarbonate diol, polyether polycarbonate diol, and polyether polyol obtained by adding alkylene oxide to polyoxytetramethylene glycol.
  • polyester polyols include polyester polyols made of condensates of dibasic acids and alcohols, polycaprolactone polyols that are ring-opening polymers of cyclic ester compounds, and the like.
  • polycarbonate diols include condensation products of alcohols and carbonate compounds, and reaction products of alcohols and cyclic esters with carbonate compounds.
  • polyether polycarbonate diol examples include a condensate of a polyether polyol and a carbonate compound.
  • polyether carbonate polyols examples include products obtained by adding alkylene oxide and carbon dioxide to an initiator having a hydroxyl group.
  • the number average molecular weight of the polyhydric alcohol, which is a polymer, is, for example, in the range of 400 to 19,700.
  • the polyhydric phenol residue refers to a group obtained by removing hydrogen atoms from all phenolic hydroxyl groups contained in a polyhydric phenol.
  • polyhydric phenols include phenols such as bisphenol A, bisphenol F, bisphenol S, novolak, resol, and resorcinol.
  • the polyamine residue refers to a group obtained by removing one hydrogen atom from all amino groups contained in a polyamine. Examples of the polyamine include ethylene diamine, diethylene diamine, diaminodiphenylmethane, hexamethylene diamine, propylene diamine, and methylbenzenediamine.
  • linking group represented by Q 1 include, for example, organic groups having the following structure.
  • the linking group represented by Q 1 is not limited to the specific examples below.
  • * is a bond bonding to R 2 of partial structure D or partial structure E in formula (1).
  • Y 1 is a single bond or a (g+1)-valent linking group.
  • Y 1 is, for example, a group containing an etheric oxygen atom or an alkylene group which may have a divalent organopolysiloxane residue, a carbon atom, a nitrogen atom, a silicon atom, a divalent to octavalent organopolysiloxane.
  • Y 1 may be groups (g2-1) to (g2-14) described below.
  • Y 1 is preferably one containing a silyl group from the viewpoint of wear resistance, and is a group obtained by removing Si(R 1 ) n L 2 3-n from formula (3-1A-3), or a group of formula ( The group obtained by removing Si(R 1 ) n L 2 3-n from 3-1A-5), the group (g2-5), and the groups (g2-7) to (g2-14) are more preferable, and g2-5 is even more preferable.
  • g is an integer of 1 or more. In one embodiment, g is preferably from 1 to 15, more preferably from 1 to 6, from the viewpoint of the surface treatment layer's ability to reduce fingerprint visibility and abrasion resistance. In one embodiment, g is preferably 2 or more, more preferably 2 to 4, and even more preferably 2 or 3 from the viewpoint of excellent wear resistance of the surface treatment layer. In one embodiment, g is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1 from the viewpoint of the surface treatment layer having excellent properties of reducing fingerprint visibility. .
  • two or more (-Si(R 1 ) n L 2 3-n ) contained in the compound represented by formula (1) may be the same or different from each other. Good too.
  • the group represented by Y 1 (-Si(R 1 ) n L 2 3-n ) g in formula (1) is preferably group (3-1A) or group (3-1B).
  • the terminal of group (3-1A) or group (3-1B) that is bonded to the specific polyalkylene oxide chain is not -O-.
  • Q a is a single bond or a divalent linking group
  • X 31 is a group having a single bond, an alkylene group, a carbon atom, a nitrogen atom, a silicon atom, a 2- to 8-valent organopolysiloxane residue, or a (h+i+1)-valent ring
  • Q b is a single bond or a divalent linking group
  • R 31 is a hydrogen atom, a hydroxyl group or an alkyl group
  • h is an integer of 1 or more
  • i is an integer of 0 or more
  • the definitions and specific examples of R 1 , L 2 , and n are the same as the definitions and specific examples of each symbol in the reactive silyl group.
  • Q c is a single bond or a divalent linking group
  • R 32 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
  • Q d is a single bond or an alkylene group
  • R 33 is a hydrogen atom or a halogen atom
  • y is an integer from 1 to 10
  • the definitions and specific examples of R 1 , L 2 , and n are the same as the definitions and specific examples of each symbol in the reactive silyl group.
  • Q a is a single bond or a divalent linking group.
  • divalent linking groups include divalent hydrocarbon groups, divalent heterocyclic groups, -O-, -S-, -SO 2 -, -N(R d )-, -C(O) -, -Si(R a ) 2 -, and a combination of two or more thereof. Excludes the case where the terminal of Q a that is bonded to the specific polyalkylene oxide chain is -O-.
  • 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 includes, for example, an alkylene group.
  • the divalent saturated hydrocarbon group preferably has 1 to 20 carbon atoms.
  • the divalent aromatic hydrocarbon group preferably has 5 to 20 carbon atoms, such as a phenylene group.
  • the divalent 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).
  • Examples of groups combining two or more of the above-mentioned types 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 -, -C(O)N(R d )-, an alkylene group having -N(R d )C(O)- an alkylene group having an etheric oxygen atom, an alkylene group having -OC(O)-, an alkylene group having -C(O)O-, an alkylene group having -C(O)S-, - Examples include an alky
  • Q a is a single bond, -O-, -S-, -N(R d )-, -C(O)N(R d )-, -OC(O)N(R d ) -, -C(O)O-, -OC(O)-, and -C(O)S- are preferred, and single bonds, -C(O)N(R d )-, -OC(O)N( R d )- and -OC(O)- are more preferred.
  • X 31 is an alkylene group, a carbon atom, a nitrogen atom, a silicon atom, a di- to octavalent organopolysiloxane residue, or a group having a (h+i+1)-valent ring.
  • the alkylene group may have -O-, a silphenylene skeleton group, a divalent organopolysiloxane residue, 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 residue, and a dialkylsilylene group.
  • the alkylene group represented by X 31 preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms.
  • Examples of the divalent to octavalent organopolysiloxane residues include divalent organopolysiloxane residues and (w2+1)-valent organopolysiloxane residues described below.
  • the ring is a ring other than an organopolysiloxane ring.
  • the ring in X 31 means a ring other than an organopolysiloxane ring.
  • the ring in X 31 may be a monocyclic ring, a fused polycyclic ring, a bridged ring, a spiro ring, or an assembled polycyclic ring, and the atoms constituting the ring may be a carbocyclic ring consisting only of carbon atoms, or a divalent ring.
  • a heterocycle consisting of a heteroatom having the above valence and a carbon atom may also be used.
  • the bond between 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.
  • the monocyclic ring is preferably a 4- to 8-membered ring, more preferably a 5-membered ring or a 6-membered ring.
  • the fused polycyclic ring is preferably a fused polycyclic ring in which two or more 4- to 8-membered rings are fused together, and fused polycyclic rings in which 2 or 3 rings selected from 5-membered rings and 6-membered rings are bonded together; A fused polycyclic ring in which one or two rings selected from membered rings and six-membered rings and one four-membered ring are bonded is more preferred.
  • the bridged ring is preferably a bridged ring whose largest ring is a 5- or 6-membered ring
  • the spiro ring is preferably a spiro ring consisting of two 4- to 6-membered rings.
  • a collective polycyclic ring two or three rings selected from 5-membered rings and 6-membered rings are bonded via a single bond, 1 to 3 carbon atoms, or 1 heteroatom with a valence of 2 or 3.
  • a set of polycyclic rings is preferred.
  • the heteroatom constituting the ring is preferably a nitrogen atom, an oxygen atom, or a sulfur atom, and more preferably a nitrogen atom or an oxygen atom.
  • the number of heteroatoms constituting the ring is preferably 3 or less. Furthermore, when the number of heteroatoms constituting the ring is two or more, these heteroatoms may be the same or different.
  • the ring in X 31 may be a 3- to 8-membered aliphatic ring, a benzene ring, or a 3- to 8-membered aliphatic ring, from the viewpoint of easy production of the compound and superior abrasion resistance, light resistance, and chemical resistance of the surface treatment layer.
  • Heterocycle of a membered ring, a condensed ring in which two or three of these rings are fused together, a bridged ring in which the largest ring is a 5- or 6-membered ring, and two or more of these rings One type selected from the group consisting of a single bond, an alkylene group having 3 or less carbon atoms, an oxygen atom, or a sulfur atom as a connecting group is preferable.
  • Preferred rings include 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 5- or 6-membered carbon ring and a 4- to 6-membered heterocycle. It is a fused ring with a ring.
  • Specific rings include the rings shown below, a 1,3-cyclohexadiene ring, a 1,4-cyclohexadiene ring, an anthracene ring, a cyclopropane ring, a decahydronaphthalene ring, a norbornene ring, a norbornadiene ring, a furan ring, Examples include a pyrrole ring, a thiophene ring, a pyrazine ring, a morpholine ring, an aziridine ring, an isoquinoline ring, an oxazole ring, an isoxazole ring, a thiazole ring, an imidazole ring, a pyrazole ring, a pyran ring, a pyridazine ring, a pyrimidine ring, and an indene ring.
  • Q a and Q b are bonded to different ring constituent atoms.
  • Each of the i R 31s may be bonded to a separate ring atom, or two of the i R 31s may be bonded to one ring carbon atom. There may be two or more ring-constituting carbon atoms to which two R 31s are bonded.
  • X 31 is a group having a carbon atom, a nitrogen atom, a silicon atom, a 4- to 8-valent organopolysiloxane residue, or a (h+i+1)-valent ring, from the viewpoint of improving the wear resistance of the surface treatment layer. is preferable, and carbon atom is more preferable.
  • Q b is a single bond or a divalent linking group.
  • divalent linking groups include divalent hydrocarbon groups, divalent heterocyclic groups, -O-, -S-, -SO 2 -, -N(R d )-, -C(O) -, -Si(R a ) 2 -, and a combination of two or more thereof.
  • 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 includes, for example, an alkylene group.
  • the number of carbon atoms in the divalent saturated hydrocarbon group is preferably 1 to 30, more preferably 1 to 20.
  • the alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably 2 to 20 carbon atoms, such as 2, 3, 8, 9, and 11 carbon atoms.
  • the alkynylene group preferably has 2 to 20 carbon atoms, such as 2, 3, 8, 9, and 11 carbon atoms.
  • the divalent aromatic hydrocarbon group preferably has 5 to 20 carbon atoms, such as a phenylene group.
  • the divalent hydrocarbon group may be an alkenylene group having 2 to 20 carbon atoms or an alkynylene group having 2 to 20 carbon atoms.
  • 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 the above 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 -, -C(O)N(R d )-, -N(R d )C(O )-, an alkylene group having an etheric oxygen atom, an
  • Q c is a single bond, -O-, -S-, -N(R d )-, -C(O)N(R d )-, -OC(O)N(R d ) -, -C(O)O-, -OC(O)-, and -C(O)S- are preferred, and single bonds, -OC(O)N(R d )-, and -OC(O)- is more preferable. Excludes the case where the terminal of Q c that is bonded to the specific polyalkylene oxide chain is -O-.
  • R 31 is a hydrogen atom, a hydroxyl group or an alkyl group.
  • the number of carbon atoms in the alkyl group is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1.
  • h is an integer greater than or equal to 1
  • i is an integer greater than or equal to 0.
  • X 31 is a single bond or an alkylene group
  • h is 1 and i is 0.
  • X 31 is a nitrogen atom
  • h is an integer of 1 to 2
  • i is an integer of 0 to 1
  • X 31 is a carbon atom or a silicon atom
  • h is an integer of 1 to 3
  • i is an integer of 0 to 2
  • X 31 is a divalent to octavalent organopolysiloxane residue
  • h is an integer of 1 to 7
  • i is an integer of 0 to 6
  • 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
  • two or more (-Q b -Si(R 1 ) n L 2 3-n ) are the same. It may be different or different.
  • two or more (-R 31 )s may be the same or different.
  • i is preferably 0 from the viewpoint of improving the wear resistance of the surface treatment layer.
  • Q c is a single bond or a divalent linking group.
  • the definition and details of the divalent linking group are the same as those explained in Q a above.
  • R 32 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and is preferably a hydrogen atom from the viewpoint of easy production of the compound.
  • the alkyl group a methyl group is preferred.
  • Q d is a single bond or an alkylene group.
  • the alkylene group preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms. From the viewpoint of easy 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 from the viewpoint of easy production of the compound.
  • y is an integer from 1 to 10, preferably from 1 to 6.
  • Two or more [CH 2 C(R 32 )(-Q d -Si(R 1 ) n L 2 3-n )] may be the same or different.
  • groups (3-1A-1) to (3-1A-7) are preferable.
  • X 32 is -C(O)O-, -SO 2 N(R d )-, -N(R d )SO 2 -, -N(R d )C( O)-, -C(O)N(R d )-, -S-, -C(O)S-, or -N(R d )- (however, N in the formula is bonded to Q b1 do).
  • the definition of R d is as described above. s1 is 0 or 1.
  • Q b1 is an alkylene group.
  • the alkylene group may have -O-, a silphenylene skeleton group, a divalent organopolysiloxane residue, 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 residue, and a dialkylsilylene group.
  • alkylene group has -O-, a silphenylene skeleton group, a divalent organopolysiloxane residue, or a dialkylsilylene group
  • Q b1 preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, and even more preferably 2 to 6 carbon atoms.
  • (X 32 ) s1 is -C(O)N(R d )-, it is preferably an alkylene group having 2 to 6 carbon atoms (however, N in the formula is bonded to Q b1 ).
  • Q b1 is one of these groups, the compound can be easily produced.
  • group (3-1A-1) include the following groups.
  • * represents the bonding position with the specific polyalkylene oxide chain.
  • X 33 is -NH-, -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 d is as described above.
  • Q a2 is a single bond, an alkylene group, -C(O)-, or an etheric oxygen atom, -C(O)-, -C(O) between carbon atoms of an alkylene group having 2 or more carbon atoms.
  • the alkylene group represented by Q a2 preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms.
  • Ether oxygen atom -C(O)-, -C(O)O-, -OC(O)-, -C between the carbon atoms of the alkylene group having 2 or more carbon atoms represented by Q a2 (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 number of carbon atoms in the group having is preferably 2 to 10, more preferably 2 to 6.
  • Q a2 is -CH 2 -, -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -CH 2 OCH 2 CH 2 - , -CH 2 NHCH 2 CH 2 - from the viewpoint of easy production of the compound.
  • -CH 2 OC(O)CH 2 CH 2 -, or -C(O)- are preferred.
  • s2 is 0 or 1. However, when s2 is 0, Q a2 is not a single bond, and the terminal of Q a2 that is bonded to the specific polyalkylene oxide chain is not -O-. s2 is preferably 0 from the viewpoint of easy production of the compound.
  • Q b2 is an alkylene group or a group having a divalent organopolysiloxane residue, an ether oxygen atom, or -NH- between carbon atoms of an alkylene group having 2 or more 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, even more preferably 2 to 20, may be 2 to 10, or may be 2 to 6. . Examples include 2, 3, 8, 9, and 11. Further, the number of carbon atoms may be 1 to 10.
  • the number of carbon atoms in the group having a divalent organopolysiloxane residue, ether oxygen atom or -NH- between carbon atoms of the alkylene group having 2 or more carbon atoms represented by Q b2 is 2 to 10. is preferable, and 2 to 6 are more preferable.
  • the two [-Q b2 -Si(R 1 ) n L 2 3-n ] may be the same or different.
  • group (3-1A-2) include the following groups.
  • * represents the bonding position with the specific polyalkylene oxide chain.
  • ⁇ in (CH 2 ) ⁇ bonded to the reactive silyl group is an integer representing the number of methylene groups, preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, It may be from 2 to 10, or from 2 to 6. Examples include 2, 3, 8, 9, and 11. Further, the number of carbon atoms may be 1 to 10.
  • a plurality of ⁇ 's contained in the same compound may be the same or different, but are preferably the same. For example, all of the plurality of ⁇ s contained in the same compound are 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, and a single bond is preferred from the viewpoint of ease of manufacturing the compound.
  • the alkylene group which may have an etheric oxygen atom preferably has 1 to 10 carbon atoms, particularly preferably 2 to 6 carbon atoms.
  • R g is a hydrogen atom, a hydroxyl group, or an alkyl group. From the viewpoint of easy production of the compound, R g 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 even more preferably a methyl group.
  • Q b3 is an alkylene group or a group having an ether oxygen atom or a divalent organopolysiloxane residue between carbon atoms of 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, even more preferably 2 to 20, may be 2 to 10, or may be 2 to 6. . Examples include 2, 3, 8, 9, and 11. Further, the number of carbon atoms may be 1 to 10.
  • the carbon number of the group having an ether oxygen atom or a divalent organopolysiloxane residue between the carbon atoms of the alkylene group having 2 or more carbon atoms, represented by Q b3 is preferably 2 to 20, and 2 to 20. 10 is more preferable, and 2 to 6 is even more preferable.
  • 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 easy production of the compound.
  • the two [-Q b3 -Si(R 1 ) n L 2 3-n ] may be the same or different.
  • group (3-1A-3) include the following groups.
  • * represents the bonding position with the specific polyalkylene oxide chain.
  • 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.
  • 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 10 carbon atoms, more preferably 2 to 6 carbon atoms.
  • t4 is 0 or 1 (however, when Q a4 is a single bond, it is 0).
  • -Q a4 -(O) t4 - is a single bond, -CH 2 O-, -CH 2 OCH 2 -, -CH 2 OCH 2 CH 2 when s4 is 0, from the viewpoint of easy production of the compound.
  • O-, -CH 2 OCH 2 CH 2 OCH 2 -, -CH 2 OCH 2 CH 2 CH 2 CH 2 OCH 2 - are preferred (however, the left side is bonded to the specific polyalkylene oxide chain), and s4 is 1.
  • a single bond, -CH 2 -, and -CH 2 CH 2 - are preferable.
  • Q b4 is an alkylene group, and the alkylene group is -O-, -C(O)N(R d )- (the definition of R d is as described above), a silphenylene skeleton group, a divalent It may or may not have an organopolysiloxane residue or a dialkylsilylene group.
  • the alkylene group has -O- or a silphenylene skeleton group, it is preferable to have -O- or a silphenylene skeleton group between carbon atoms.
  • the terminal between carbon atoms or the side bonded to (O) u4 preferably has these groups.
  • the number of carbon atoms in the alkylene group represented by Q b4 is preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, may be 2 to 10, or may be 2 to 6. . Examples include 2, 3, 8, 9, and 11. Further, the range may be from 1 to 10.
  • u4 is 0 or 1.
  • -(O) u4 -Q b4 - includes -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -CH 2 OCH 2 CH 2 CH 2 -, -CH 2 from the viewpoint of easy production of the compound.
  • OCH 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 -- and --CH 2 CH 2 CH 2 Si(CH 3 ) 2 PhSi(CH 3 ) 2 CH 2 CH 2 -- are preferred (however, the right side is bonded to Si).
  • w1 is an integer from 0 to 2, preferably 0 or 1, and more preferably 0. If there are two or more [-(O) u4 -Q b4 -Si(R 1 ) n L 2 3-n ], two or more [-(O) u4 -Q b4 -Si(R 1 ) n L 2 3-n ] may be the same or different. When there are two or more R 31 s, two or more (-R 31 )s may be the same or different.
  • group (3-1A-4) include the following groups.
  • * represents the bonding position with the specific polyalkylene oxide chain.
  • X 34 is -C(O)O-, -SO 2 N(R d )-, -N(R d )SO 2 -, -N(R d )C( O)-, -C(O)N(R d )-, -S-, -C(O)S-, or -N(R d )- (however, N in the formula is bonded to Q b1 do).
  • the definition of R d is as described above.
  • s3 is 0 or 1.
  • Q a5 is an alkylene group which may have an ether oxygen atom.
  • the alkylene group which may have an etheric oxygen atom preferably has 1 to 10 carbon atoms, particularly preferably 2 to 6 carbon atoms.
  • Q a5 from the viewpoint of easy production of the compound, when s3 is 0, -CH 2 OCH 2 CH 2 CH 2 -, -CH 2 OCH 2 CH 2 OCH 2 CH 2 CH 2 -, -CH 2 CH 2- , -CH 2 CH 2 CH 2 - are preferred (however, the right side is bonded to Si).
  • Q a5 is preferably -CH 2 CH 2 CH 2 - or -CH 2 CH 2 OCH 2 CH 2 CH 2 - from the viewpoint of easy production of the compound.
  • Q a5 is preferably an alkylene group having 2 to 6 carbon atoms from the viewpoint of easy production of the compound (however, N in the formula Q a5 ).
  • Q b5 is an alkylene group or a group having an ether oxygen atom or a divalent organopolysiloxane residue between carbon atoms of 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, even more preferably 2 to 20, may be 2 to 10, or may be 2 to 6. . Examples include 2, 3, 8, 9, and 11. Further, the number of carbon atoms may be 1 to 10.
  • the number of carbon atoms in the group having an ether oxygen atom or a divalent organopolysiloxane residue between carbon atoms of the alkylene group having 2 or more carbon atoms represented by Q b5 is preferably 2 to 20, and 2 to 20. 10 is more preferable, and 2 to 6 is even more preferable.
  • Q b5 is preferably -CH 2 CH 2 CH 2 - and -CH 2 CH 2 OCH 2 CH 2 CH 2 - (provided that the right side is Si(R 1 ) n L 2 3-n .).
  • the three [-Q b5 -Si(R 1 ) n L 2 3-n ] may be the same or different.
  • group (3-1A-5) include the following groups.
  • * represents the bonding position with the specific polyalkylene oxide chain.
  • Q a6 is an alkylene group which may have an ether oxygen atom.
  • the alkylene group which may have an etheric oxygen atom preferably has 1 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
  • Q a6 is -CH 2 OCH 2 CH 2 CH 2 -, -CH 2 OCH 2 CH 2 OCH 2 CH 2 CH 2 -, -CH 2 CH 2 - , -CH 2 CH 2 from the viewpoint of easy production of the compound. 2 CH 2 - is preferred (provided that the right side is bonded to Z a ).
  • Z a is a (w2+1)-valent organopolysiloxane residue or a (w2+1)-valent group having an alkylene group between the organopolysiloxane residues.
  • w2 is an integer from 2 to 7.
  • Examples of (w2+1)-valent organopolysiloxane residues and (w2+1)-valent groups having an alkylene group between organopolysiloxane residues include the following groups: .
  • R a in the following formula is as described above.
  • Q b6 is an alkylene group or a group having an ether oxygen atom or a divalent organopolysiloxane residue between carbon atoms of 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, even more preferably 2 to 20, may be 2 to 10, or may be 2 to 6. . Examples include 2, 3, 8, 9, and 11. Further, the number of carbon atoms may be 1 to 10.
  • the carbon number of the group having an ether oxygen atom or a divalent organopolysiloxane residue between the carbon atoms of the alkylene group having 2 or more carbon atoms represented by Q b6 is preferably 2 to 20, and 2 to 20. 10 is more preferable, and 2 to 6 is even more preferable.
  • Q b6 -CH 2 CH 2 - and -CH 2 CH 2 CH 2 - are preferable from the viewpoint of easy production of the compound.
  • w2 [-Q b6 -Si(R 1 ) n3 L 2 3-n ] may be the same or different.
  • group (3-1A-6) include the following groups.
  • * represents the bonding position with the specific polyalkylene oxide chain.
  • Z c is a (w3+w4+1)-valent hydrocarbon group.
  • w3 is an integer of 4 or more.
  • w4 is an integer greater than or equal to 0.
  • the definitions and preferred ranges of Q e , s4, Q a4 , t4, Q b4 , and u4 are the same as the definitions of each symbol in group (3-1A-4).
  • Z c may consist of a hydrocarbon chain, may have an ether oxygen atom between carbon atoms of the hydrocarbon chain, and is preferably composed of a hydrocarbon chain.
  • the valence of Z c is preferably 5 to 20, more preferably 5 to 10, even more preferably 5 to 8, particularly preferably penta or hexavalent.
  • the number of carbon atoms in Z c is preferably 3 to 50, more preferably 4 to 40, even more preferably 5 to 30.
  • w3 is preferably 4 to 20, more preferably 4 to 16, even more preferably 4 to 8, and particularly preferably 4 or 5.
  • w4 is preferably 0 to 10, more preferably 0 to 8, even more preferably 0 to 6, particularly preferably 0 to 3, and most preferably 0 or 1.
  • two or more [-(O-Q b4 ) u4 -Si(R 1 ) n L 2 3-n ] may be the same or different.
  • group (3-1A-7) include the following groups.
  • * represents the bonding position with the specific polyalkylene oxide chain.
  • the A 1 side is connected to the specific polyalkylene oxide chain, and the Q 22 , Q 23 , Q 24 , Q 25 or Q 26 side is (-Si(R 1 ) n L 2 3-n ). Furthermore, in formulas (g2-1) to (g2-7), the terminal bonded to the specific polyalkylene oxide chain is not -O-.
  • a 1 is a single bond, -C(O)NR 6 -, -C(O)-, -NHC(O)O-, -NHC(O)NR 6 -, NR 6 -, or SO 2 NR 6 - It is.
  • Q 11 is a single bond, -O-, an alkylene group, or a bond between carbon atoms of an alkylene group having 2 or more carbon atoms -C(O)NR 6 -, -C(O)-, -NR 6 -, or It is a group having O-.
  • Q 12 has -C(O)NR 6 -, -C(O)-, -NR 6 - or O- between carbon atoms of a single bond, an alkylene group, or an alkylene group having 2 or more carbon atoms. It is the basis.
  • Q 13 is a single bond, an alkylene group, 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; , or a group having -C(O)- at the N-side end of the alkylene group.
  • Q 14 is Q 12 when the atom in Z 1 to which Q 14 is bonded is a carbon atom, and is Q 13 when the atom in Z 1 to which Q 14 is bonded is a nitrogen atom.
  • Q 15 has -C(O)NR 6 -, -C(O)-, -NR 6 - or O- between carbon atoms of a single bond, an alkylene group, or an alkylene group having 2 or more carbon atoms. It is the basis.
  • Q 22 is an alkylene group, 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, an alkylene group A group having -C(O)NR 6 -, -C(O)-, -NR 6 - or O- at the end not connected to Si, or between carbon atoms of an alkylene group having 2 or more carbon atoms -C(O)NR 6 -, -C(O)-, -NR 6 - or O- at the end not connected to Si and -C(O)NR 6 -, -C(O) It is a group having -, -NR 6 - or O-, and when Y 1 has two or more Q 22s , two or more Q 22s 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; , two Q23s may be the same or different.
  • Q 24 is Q 22 when the atom in Z 1 to which Q 24 is bonded is a carbon atom, and Q 23 when the atom in Z 1 to which Q 24 is bonded is a nitrogen atom; When there are two or more, two or more Q24 may be the same or different.
  • Q 25 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; , Y 1 has two or more Q 25s , the two or more Q 25s may be the same or different.
  • Q 26 is a single bond, an alkylene group, or a carbon-carbon atom of an alkylene group having 2 or more carbon atoms with -C(O)NR 6 -, -C(O)-, -NR 6 - or -O-. It is a group that has However, when A1 is a single bond, Q26 is a group other than a single bond.
  • Z 1 is a group having an h1+h2 valent ring structure in which Q 14 has a carbon atom or nitrogen atom to which Q 24 is directly bonded, and Q 24 has 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 Y 1 has two or more R e1s , the two or more R e1s 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 from 0 to 1.
  • d2 is an integer from 0 to 3, preferably 1 or 2.
  • d1+d2 is an integer from 1 to 3.
  • d3 is an integer from 0 to 1.
  • d4 is an integer from 0 to 3, preferably 2 or 3.
  • d3+d4 is an integer from 1 to 3.
  • d1+d3 is 1.
  • d2+d4 is an integer from 1 to 5, preferably 4 or 5.
  • e1+e2 is 3 or 4.
  • e1 is 1.
  • e2 is an integer from 1 to 3, preferably 2 or 3.
  • h1 is 1.
  • h2 is an integer of 1 or more, preferably 2 or 3.
  • i1+i2 is 3 or 4.
  • i1 is 1.
  • i2 is an integer from 1 to 3, preferably 2 or 3. i3 is 2 or 3.
  • the number of carbon atoms in the alkylene groups of Q 11 , Q 12 , Q 13 , Q 14 , Q 15 , Q 22 , Q 23 , Q 24 , Q 25 and Q 26 is determined from the viewpoint of easy production of compound (1) and surface treatment. From the viewpoint of further improving the abrasion resistance of the layer, the number is preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, may be 2 to 10, or may be 2 to 6. Examples include 2, 3, 8, 9, and 11. Further, the number of carbon atoms may be 1 to 10, 1 to 6, or 1 to 4. However, when the alkylene group has a specific bond between carbon atoms, the lower limit of the number of carbon atoms is 2.
  • Examples of the ring structure in Z 1 include the ring structures described above, and preferred forms are also the same.
  • Q 14 and Q 24 are directly bonded to the ring structure in Z 1 , for example, an alkylene group is not connected to the ring structure and Q 14 or Q 24 is not connected 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 even more preferably 1 to 2 from the viewpoint of ease of producing compound (1).
  • the number of carbon atoms in the alkyl group moiety of the acyloxy group in R e2 is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2 from the viewpoint of ease of producing compound (1).
  • h2 is preferably 2 to 6, more preferably 2 to 4, and even more preferably 2 or 3, from the viewpoint of facilitating the production of compound (1) and the viewpoint of further improving the abrasion resistance of the surface treatment layer.
  • the A 1 side is connected to the specific polyalkylene oxide chain, and the G 1 side is connected to (-Si(R 1 ) n L 2 3-n ).
  • G 1 is a group (g3), and two or more G 1s in Y 1 may be the same or different.
  • the symbols other than G 1 are the same as those in equations (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 (-Si(R 1 ) n L 2 3-n ).
  • 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 carbon atoms of an alkylene group having 2 or more carbon atoms, or (OSi(R 9 ) 2 ) p -O-, and two or more Q 3 may be the same or different.
  • 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 from 0 to 5, and when p is 2 or more, two or more (OSi(R 9 ) 2 ) may be the same or different.
  • the terminal bonded to the specific polyalkylene oxide chain is not -O-.
  • the number of carbon atoms in the alkylene group of Q3 is preferably 1 to 30, more preferably 1 to 20, more preferably 2 to 20 is more preferable, and may be 2 to 10, or may be 2 to 6. Examples include 2, 3, 8, 9, and 11. Further, the number of carbon atoms may be 1 to 10, 1 to 6, or 1 to 4. However, when the alkylene group has a specific bond between carbon atoms, the lower limit of the number of carbon atoms 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 to 2 from the viewpoint of ease of producing compound (1).
  • 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 to 2 from the viewpoint of ease of producing compound (1).
  • the number of carbon atoms in the alkoxy group of R 9 is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2 from the viewpoint of excellent storage stability of compound (1).
  • p is preferably 0 or 1.
  • Examples of the partial structure D of compound (1) include the partial structure of the following formula.
  • a compound having the partial structure of the following formula as partial structure D is preferable from the viewpoints of being easy to industrially produce, easy to handle, and providing a surface treatment layer with excellent abrasion resistance.
  • R t in the compound of the following formula is the same as -(R 2 O) a2 (CH 2 CH 2 O) b2 - in the above-mentioned formula (1), and the preferred forms are also the same.
  • Examples of the partial structure D in which Y 1 is a group (g2-1) include partial structures of the following formula.
  • Examples of the partial structure D in which Y 1 is a group (g2-2) include partial structures of the following formula.
  • Examples of the partial structure D in which Y 1 is a group (g2-3) include partial structures of the following formula.
  • Examples of the partial structure D in which Y 1 is a group (g2-4) include partial structures of the following formula.
  • Examples of partial structure D in which Y 1 is a group (g2-5) include partial structures of the following formula.
  • Examples of partial structure D in which Y 1 is a group (g2-6) include partial structures of the following formula.
  • Examples of partial structure D in which Y 1 is a group (g2-7) include partial structures of the following formula.
  • Examples of partial structure D in which Y 1 is a group (g2-8) include partial structures of the following formula.
  • Examples of the partial structure D in which Y 1 is a group (g2-9) include partial structures of the following formula.
  • Examples of the partial structure D in which Y 1 is a group (g2-10) include partial structures of the following formula.
  • Examples of the partial structure D in which Y 1 is a group (g2-11) include partial structures of the following formula.
  • Examples of the partial structure D in which Y 1 is a group (g2-12) include partial structures of the following formula.
  • Examples of partial structure D in which Y 1 is a group (g2-13) include partial structures of the following formula.
  • Examples of partial structure D in which Y 1 is a group (g2-14) include partial structures of the following formula.
  • Examples of the compounds of the present disclosure include the following compounds.
  • a1 to a4 and b1 to b4 are each independently an integer of 1 to 300
  • a11, a12, a21, and a22 are each independently an integer of 1 to 299
  • a11+a12 is 2 to 300.
  • a21+a22 is an integer of 2 to 300.
  • the number average molecular weight (Mn) of the compound of the present disclosure is preferably 400 to 20,000, more preferably 500 to 18,000, even more preferably 600 to 15,000, and even more preferably 700 to 18,000. 10,000 is particularly preferred, and 800 to 6,000 is most preferred. If Mn is 400 or more, the property of reducing fingerprint visibility and the abrasion resistance are excellent. When Mn is 20,000 or less, the viscosity can be easily controlled within an appropriate range, and solubility is improved, resulting in excellent handling properties during film formation.
  • the method for producing the compound of the present disclosure is not particularly limited.
  • An example of a method for producing the compound of the present disclosure includes the following method. Specifically, first, at least one selected from the group consisting of polyhydric alcohols, polyhydric phenols, and polyamines having a linking group structure represented by Q 1 in formula (1) above is used as an initiator. . Then, by polymerizing ethylene oxide and an alkylene oxide having 3 to 6 carbon atoms in the presence of potassium hydroxide, a compound in which a specific polyalkylene oxide chain is bonded to the linking group Q is obtained. Furthermore, the compound of the present disclosure is obtained by reacting a portion of the terminal hydroxy group of the specific polyalkylene oxide chain with a compound having a group capable of reacting with the hydroxy group and a reactive silyl group.
  • examples of the group capable of reacting with a hydroxy group in a compound having a group capable of reacting with a hydroxy group and a reactive silyl group include an isocyanato group, an amino group, a mercapto group, and the like.
  • the value of Ma/(Ma+Mb) in the obtained compound can be controlled by controlling the amount of ethylene oxide and the amount of alkylene oxide having 3 to 6 carbon atoms, which are added when ethylene oxide and alkylene oxide having 3 to 6 carbon atoms are polymerized. Examples include a method of adjusting the ratio to the amount added.
  • some of the terminal hydroxy groups of the specific polyalkylene oxide chain examples include a method of adjusting the amount of the compound having a reactive silyl group added when reacting the compound having a reactive silyl group.
  • compositions of the present disclosure only needs to contain the compound of the present disclosure, and components other than the compound of the present disclosure are not particularly limited.
  • Compositions of the present disclosure preferably include a compound of the present disclosure and a liquid medium.
  • the composition of the present disclosure may be in a liquid state, and may be a solution or a dispersion.
  • the composition of the present disclosure only needs to contain the compound of the present disclosure, and may contain impurities such as by-products generated in the manufacturing process of the compound of the present disclosure.
  • the composition of the present disclosure may contain one type of compound of the present disclosure, or may contain two or more types of compounds of the present disclosure.
  • the content of the compound of the present disclosure is preferably 0.001 to 40% by mass, more preferably 0.01 to 20% by mass, and further preferably 0.1 to 10% by mass, based on the total amount of the composition of the present disclosure.
  • the content of the compound of the present disclosure in the composition of the present disclosure used in the wet coating method may be 0.01 to 10% by mass, and 0.02 to 5% by mass, based on the total amount of the composition of the present disclosure. It may be 0.03 to 3 mass %, or 0.05 to 2 mass %.
  • the liquid medium preferably contains an organic solvent and water.
  • organic solvents include compounds consisting only of hydrogen atoms and carbon atoms, and compounds consisting only of hydrogen atoms, carbon atoms, and oxygen atoms.
  • examples include hydrocarbon-based organic solvents, ketone-based organic solvents, and ethers.
  • examples include organic solvents based on organic solvents, organic solvents based on esters, organic solvents based on glycol, and organic solvents based on alcohol.
  • hydrocarbon organic solvents include pentane, hexane, heptane, octane, hexadecane, isohexane, isooctane, isononane, cycloheptane, cyclohexane, bicyclohexyl, benzene, toluene, ethylbenzene, o-xylene, m-xylene, Examples include p-xylene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, n-butylbenzene, sec-butylbenzene, and tert-butylbenzene.
  • ketone organic solvents include acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, 2-heptanone, 4-heptanone, 3,5,5-trimethyl-2-cyclohexen-1-one, and 3,5,5-trimethyl-2-cyclohexen-1-one. Examples include 3,5-trimethylcyclohexanone and isophorone.
  • ether organic solvents include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, and 1,4-dioxane.
  • ester organic solvents include methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate, tert-butyl acetate, amyl acetate, isoamyl acetate, ethyl 3-ethoxypropionate, and ethyl ethylene glycol lactate.
  • glycol-based organic solvents include ethylene glycol, ethylene glycol monobutyl ether, diethylene glycol monobutyl ether, triethylene glycol monobutyl ether, tetraethylene glycol monobutyl ether, ethylene glycol monohexyl ether, diethylene glycol monohexyl ether, and ethylene glycol mono-2.
  • alcoholic organic solvents include methanol, ethanol, 1-propanol, isopropyl alcohol, n-butanol, diacetone alcohol, isobutanol, sec-butanol, tert-butanol, pentanol, 3-methyl-1,3 -Butanediol, 1,3-butanediol, 1,3-butylene glycol, octanediol, 2,4-diethylpentanediol, butylethylpropanediol, 2-methyl-1,3-propanediol, 4-hydroxy-4 -Methyl-2-pentanone, 2-ethyl-1-hexanol, 3,5,5-trimethyl-1-hexanol, isodecanol, isotridecanol, 3-methoxy-3-methyl-1-butanol, 2-methoxybutanol , 3-methoxybutanol, cyclo
  • examples of the organic solvent include halogenated organic solvents, nitrogen-containing compounds, sulfur-containing compounds, and siloxane compounds.
  • halogenated organic solvents include dichloromethane, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, o-chlorotoluene, m-chlorotoluene, p-chlorotoluene, m-dichlorobenzene, 1,2,3-trichloropropane. can be mentioned.
  • nitrogen-containing compounds include nitrobenzene, acetonitrile, benzonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and 1,3-dimethyl-2-imidazolidinone.
  • sulfur-containing compounds include carbon disulfide and dimethyl sulfoxide.
  • siloxane compound include hexamethyldisiloxane, octamethyltrisiloxane, and decamethyltetrasiloxane.
  • Two or more kinds of organic solvents may be mixed, for example, a glycol-based organic solvent and an alcohol-based organic solvent may be mixed.
  • the content of the organic solvent is preferably 90 to 99% by mass, more preferably 93 to 99% by mass, and even more preferably 95 to 99% by mass, based on the total amount of the liquid medium.
  • the water content is preferably 1 to 10% by mass, more preferably 1 to 7% by mass, and even more preferably 1 to 5% by mass, based on the total amount of the liquid medium.
  • the content of the liquid medium is preferably 60 to 99.999% by mass, more preferably 80 to 99.99% by mass, and even more preferably 90 to 99.9% by mass, based on the total amount of the composition of the present disclosure.
  • the content of the liquid medium may be 90-99.99% by weight, 95-99% by weight, based on the total amount of the composition of the present disclosure. It may be .98% by mass, 97 to 99.97% by mass, or 98 to 99.95% by mass.
  • the composition of the present disclosure may contain only one type of liquid medium, or may contain two or more types.
  • composition of the present disclosure may contain other components in addition to the compound of the present disclosure and the liquid medium, as long as the effects of the present disclosure are not impaired.
  • other components include known additives such as acid catalysts and basic catalysts that promote hydrolysis and condensation reactions of reactive silyl groups.
  • acid catalysts include hydrochloric acid, nitric acid, acetic acid, sulfuric acid, phosphoric acid, sulfonic acid, methanesulfonic acid, and p-toluenesulfonic acid.
  • acid catalysts include hydrochloric acid, nitric acid, acetic acid, sulfuric acid, phosphoric acid, sulfonic acid, methanesulfonic acid, and p-toluenesulfonic acid.
  • basic catalysts include sodium hydroxide, potassium hydroxide, and ammonia.
  • a metal compound having a hydrolyzable group is also referred to as a "specific metal compound”
  • Specific metal compounds include the following formulas (M1) to (M3).
  • M represents a trivalent or tetravalent metal atom.
  • Each of X b1 independently represents a hydrolyzable group.
  • Each of X b2 independently represents a siloxane skeleton-containing group.
  • Each of X b3 independently represents a hydrocarbon chain-containing group.
  • m1 is an integer from 2 to 4
  • m2 and m3 are each independently an integer of 0 to 2
  • When M is a trivalent metal atom, m1+m2+m3 is 3, and when M is a tetravalent metal atom, m1+m2+m3 is 4.
  • X b4 represents a hydrolyzable silane oligomer residue.
  • Each of X b5 independently represents a hydrolyzable group or an alkyl group having 1 to 4 carbon atoms.
  • X b6 and X b7 each independently represent a hydrolyzable group or a hydroxyl group.
  • Y b1 represents a divalent organic group.
  • the metal represented by M also includes semimetals such as Si and Ge.
  • M is preferably a trivalent metal or a tetravalent metal, more preferably Al, Fe, In, Hf, Si, Ti, Sn, and Zr, even more preferably Al, Si, Ti, and Zr, and particularly preferably Si. .
  • the hydrolyzable group represented by X b1 is the hydrolyzable group represented by L 2 in (-Si(R 1 ) n L 2 3-n ) in the above reactive silyl group. The same can be mentioned.
  • the siloxane skeleton-containing group represented by X b2 has a siloxane unit (-Si-O-) and may be linear or branched.
  • the siloxane unit is preferably a dialkylsilyloxy group, such as a dimethylsilyloxy group or a diethylsilyloxy group.
  • the number of repeating siloxane units in the siloxane skeleton-containing group is 1 or more, preferably 1 to 5, more preferably 1 to 4, and even more preferably 1 to 3.
  • the siloxane skeleton-containing group may include a divalent hydrocarbon group in a part of the siloxane skeleton.
  • some oxygen atoms in the siloxane skeleton may be replaced with divalent hydrocarbon groups.
  • the divalent hydrocarbon group include alkylene groups such as a methylene group, an ethylene group, a propylene group, and a butylene group.
  • a hydrolyzable group, a hydrocarbon group (preferably an alkyl group), etc. may be bonded to the terminal silicon atom of the siloxane skeleton-containing group.
  • the number of elements in the siloxane skeleton-containing group is preferably 100 or less, more preferably 50 or less, and even more preferably 30 or less. The number of elements is preferably 10 or more.
  • the siloxane skeleton-containing group is preferably a group represented by * -(O-Si(CH 3 ) 2 ) n CH 3 , where n is an integer from 1 to 5, and * represents a bond with an adjacent atom. Represents a part.
  • the hydrocarbon chain-containing group represented by X b3 may be a group consisting only of a hydrocarbon chain, or may be a group having an etheric oxygen atom between carbon atoms of the hydrocarbon chain.
  • the hydrocarbon chain may be straight or branched, preferably straight.
  • the hydrocarbon chain may be a saturated hydrocarbon chain or an unsaturated hydrocarbon chain, with a saturated hydrocarbon chain being preferred.
  • the number of carbon atoms in the hydrocarbon chain-containing group is preferably 1 to 3, more preferably 1 to 2, and even more preferably 1.
  • the hydrocarbon chain-containing group is preferably an alkyl group, more preferably a methyl group, an ethyl group, or a propyl group.
  • m1 is 3 or 4.
  • compound represented by formula (M1) compounds represented by the following formulas (M1-1) to (M1-5) where M is Si are preferable, and the compound represented by formula (M1-1) is More preferred.
  • compound represented by formula (M1-1) tetraethoxysilane, tetramethoxysilane, and triethoxymethylsilane are preferred.
  • the number of silicon atoms contained in the hydrolyzable silane oligomer residue represented by X b4 is preferably 3 or more, more preferably 5 or more, and even more preferably 7 or more.
  • the number of silicon atoms is preferably 15 or less, more preferably 13 or less, and even more preferably 10 or less.
  • the hydrolyzable silane oligomer residue may have an alkoxy group bonded to a silicon atom. Examples of the alkoxy group include methoxy group, ethoxy group, propoxy group, butoxy group, and methoxy group and ethoxy group are preferred.
  • the hydrolyzable silane oligomer residue may have one or more types of these alkoxy groups, and preferably has one type. Examples of the hydrolyzable silane oligomer residue include (C 2 H 5 O) 3 Si-(OSi(OC 2 H 5 ) 2 ) 4 O- * and the like.
  • * represents a bonding site with an adjacent atom.
  • the hydrolyzable group represented by X b5 is the hydrolyzable group represented by L 2 in (-Si(R 1 ) n L 2 3-n ) in the above reactive silyl group.
  • Examples include those similar to , a cyano group, a hydrogen atom, and an allyl group, with an alkoxy group or an isocyanato group being preferred.
  • the alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms.
  • X b5 a hydrolyzable group is preferable.
  • Examples of the compound represented by formula (M2) include (H 5 C 2 O) 3 -Si-(OSi(OC 2 H 5 ) 2 ) 4 OC 2 H 5 and the like.
  • the compound represented by formula (M3) is a compound having a reactive silyl group at both ends of a divalent organic group, that is, bissilane.
  • the hydrolyzable groups represented by X b6 and X b7 include an alkoxy group, an acyloxy group, a ketoxime group, an alkenyloxy group, an amino group, an aminoxy group, an amide group, an isocyanato group, and a halogen atom.
  • an alkoxy group and an isocyanato group are preferred.
  • the alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms, more preferably a methoxy group or an ethoxy group.
  • X b6 and X b7 may be the same group or different groups. From the viewpoint of availability, it is preferable that X b6 and X b7 are the same group.
  • Y b1 is a divalent organic group that connects the reactive silyl groups at both ends.
  • the number of carbon atoms in Y b1 of the divalent organic group is preferably 1 to 8, more preferably 1 to 3.
  • Examples of Y b1 include an alkylene group, a phenylene group, and an alkylene group having an etheric oxygen atom between carbon atoms.
  • Examples of the compound represented by formula (M3) include (CH 3 O) 3 Si(CH 2 ) 2 Si(OCH 3 ) 3 , (C 2 H 5 O) 3 Si(CH 2 ) 2 Si(OC 2 H 5 ) 3 , (OCN) 3Si ( CH2 ) 2Si ( NCO ) 3 , Cl3Si( CH2 ) 2SiCl3 , ( CH3O ) 3Si ( CH2 ) 6Si ( OCH3 ) 3 , ( C2H5O ) 3Si ( CH2 ) 6Si ( OC2H5 ) 3 is mentioned.
  • the content of other components that may be included in the composition of the present disclosure is preferably 10% by mass or less, more preferably 1% by mass or less, based on the total amount of the composition of the present disclosure.
  • the content of the specific metal compound is preferably 0.01 to 30% by mass, more preferably 0.01 to 10% by mass based on the total amount of the composition of the present disclosure. , more preferably 0.05 to 5% by mass.
  • the total content of the compound of the present disclosure and other components is preferably 0.001 to 40% by mass, and 0.01% by mass, based on the total amount of the composition of the present disclosure. ⁇ 20% by mass is more preferred, and 0.1 ⁇ 10% by mass is even more preferred.
  • the solid content concentration of the composition of the present disclosure is a value calculated from the mass of the composition before heating and the mass after heating in a convection dryer at 120° C. for 4 hours.
  • composition of the present disclosure contains a liquid medium, it is useful for coating purposes and can be used as a coating liquid.
  • the surface treatment agent of the present disclosure comprises a compound of the present disclosure.
  • the surface treatment agent of the present disclosure may include the compound of the present disclosure and a liquid medium.
  • the surface treating agent of the present disclosure may be a composition of the present disclosure. Preferred embodiments of the liquid medium contained in the surface treatment agent are the same as those of the liquid medium contained in the composition of the present disclosure.
  • the compound of the present disclosure has the above-mentioned structure, by using a surface treatment agent containing the compound of the present disclosure, it is possible to form a surface treatment layer with excellent properties of reducing fingerprint visibility and excellent abrasion resistance.
  • the article of the present disclosure includes a base material and a surface treatment layer surface treated with the surface treatment agent.
  • the surface treatment layer may be formed on a part of the surface of the base material, or may be formed on the entire surface of the base material.
  • the surface treatment layer may be spread over the surface of the base material 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 hydrolysis of some or all of the reactive silyl groups has proceeded, and a dehydration condensation reaction of the silanol groups has proceeded.
  • the thickness of the surface treatment layer is preferably 1 to 100 nm, 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 sufficiently obtained. 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 is determined by using an X-ray diffractometer for thin film analysis (product name "ATX-G", manufactured by RIGAKU) to obtain an interference pattern of reflected X-rays by the X-ray reflectance method. It can be calculated from the vibration period of
  • the contact angle of water on the surface of the surface treatment layer is preferably 7 degrees or less, more preferably 6 degrees or less, and even more preferably 5 degrees or less.
  • the lower limit of the contact angle of water on the surface of the surface treatment layer is not particularly limited, and may be, for example, 2 degrees.
  • the water contact angle is a value measured in accordance with JIS R 3257:1999 "Method for testing wettability of substrate glass surface.” Specifically, water droplets are placed at five locations on the surface of the surface treatment layer to be measured, and the contact angle of water is measured for each water droplet by the sessile drop method. The amount of water droplets is approximately 2 ⁇ L/drop, and the measurement is performed in an environment at a temperature of 23° C., and the average value of the measured values at 5 locations is defined as the above-mentioned “water contact angle”.
  • the type of base material is not particularly limited, and includes, for example, base materials that are required to have characteristics that reduce fingerprint visibility.
  • a base material for example, a base material that may be used in contact with another article (e.g., a stylus) or a person's fingers; a base material that may be held by a person's fingers during operation; , a mounting table).
  • the base material include metal, resin, glass, sapphire, ceramic, stone, fiber, nonwoven fabric, paper, wood, natural leather, artificial leather, and composite materials thereof.
  • the glass may be chemically strengthened.
  • Base materials include building materials, decorative building materials, interior goods, transportation equipment (e.g. automobiles), signboards/bulletin boards, drinking vessels/tableware, aquariums, ornamental equipment (e.g. frames, boxes), laboratory equipment, furniture, textile products. , Packaging containers; Glass or resin used for art, sports, games, etc.; Used for the exterior parts (excluding display parts) of devices such as mobile phones (e.g. smartphones), personal digital assistants, game consoles, remote controls, etc. Examples include glass or resin.
  • the shape of the base material may be a plate shape or a film shape.
  • touch panel base materials As the base material, touch panel base materials, display base materials, and eyeglass lenses are suitable, and touch panel base materials are particularly suitable.
  • touch panel base materials As the material for the touch panel base material, glass or transparent resin is preferable.
  • the base material may be a base material that has been subjected to surface treatment such as corona discharge treatment, plasma treatment, plasma graft polymerization treatment, etc. on one surface or both surfaces.
  • the surface-treated base material has better adhesion with the surface-treated layer, and the abrasion resistance of the surface-treated layer is further improved. Therefore, it is preferable to perform surface treatment on the surface of the base material that is in contact with the surface treatment layer. Further, when the surface-treated base material is provided with a base layer, which will be described later, the adhesion with the base layer is better, and the wear resistance of the surface-treated layer is further improved. Therefore, when a base layer is provided, it is preferable to perform a surface treatment on the surface of the base material that is in contact with the base layer.
  • the surface treatment layer may be provided directly on the surface of the base material, or a base layer may be provided between the base material and the surface treatment layer.
  • the article of the present disclosure includes a base material, a base layer disposed on the base material, and a base layer disposed on the base layer. It is preferable to include a surface treatment layer whose surface is treated with the surface treatment agent of the present disclosure.
  • the base layer includes silicon and at least one selected from the group consisting of a group 1 element, a group 2 element, a group 4 element, a group 5 element, a group 13 element, and a group 15 element of the periodic table.
  • a layer containing an oxide containing a specific element is preferable.
  • Group 1 elements of the periodic table mean lithium, sodium, potassium, rubidium, and cesium.
  • Group 1 elements lithium, sodium, and potassium are used because they enable the surface treatment layer to be formed more uniformly on the underlayer without defects, and from the viewpoint of suppressing variations 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 mean beryllium, magnesium, calcium, strontium, and barium.
  • Group 2 elements magnesium, calcium, and barium are used because they enable the surface treatment layer to be formed more uniformly on the underlayer without defects, and from the viewpoint of suppressing variations in the composition of the underlayer between samples.
  • magnesium and calcium are more preferable.
  • the underlayer may contain two or more types of Group 2 elements.
  • Group 4 elements of the periodic table mean titanium, zirconium, and hafnium.
  • Group 4 element titanium and zirconium are preferable from the viewpoint of being able to form a surface treatment layer on the underlayer more uniformly without defects or from the viewpoint of suppressing variations in the composition of the underlayer between samples. Titanium is more preferred.
  • the base layer may contain two or more types of Group 4 elements.
  • Group 5 elements of the periodic table mean vanadium, niobium, and tantalum.
  • Group 5 element vanadium is particularly preferable from the viewpoint of providing better wear resistance of the surface treatment layer.
  • the underlayer may contain two or more types of Group 5 elements.
  • Group 13 elements of the periodic table mean boron, aluminum, gallium, and indium.
  • Group 13 elements boron, aluminum, and gallium are selected from the viewpoint of forming a surface treatment layer on the underlayer more uniformly without defects, or from the viewpoint of suppressing variations in the composition of the underlayer between samples.
  • boron and aluminum are more preferable.
  • the base layer may contain two or more types of Group 13 elements.
  • Group 15 elements of the periodic table mean nitrogen, phosphorus, arsenic, antimony, and bismuth.
  • Group 15 elements, phosphorus, antimony, and bismuth are used from the viewpoint of forming a surface treatment layer on the underlayer more uniformly without defects or from the viewpoint of suppressing variations in the composition of the underlayer between samples.
  • phosphorus and bismuth are more preferable.
  • the base layer may contain two or more types of Group 15 elements.
  • Group 1 elements, Group 2 elements, and Group 13 elements are preferable because the wear resistance of the surface treatment layer is better, and Group 1 elements and Group 2 elements are more preferable. , Group 1 elements are more preferred. As the specific element, only one type of element may be included, or two or more types of elements may be included.
  • the oxide contained in the base layer may be a mixture of oxides of the above elements (silicon and specific elements) alone (for example, a mixture of silicon oxide and an oxide of a specific element), or a mixture of the above elements (silicon and specific elements). It may be a composite oxide containing two or more types, or a mixture of an oxide of the above element alone and a composite oxide.
  • the ratio of the total molar concentration of the specific element in the underlayer to the molar concentration of silicon in the underlayer (specific element/silicon) is 0.02 to 2.90 from the viewpoint of better wear resistance of the surface treatment layer. It is preferably 0.10 to 2.00, even more preferably 0.20 to 1.80.
  • the molar concentration (mol %) of each element in the underlayer can be measured, for example, by depth direction analysis using X-ray photoelectron spectroscopy (XPS) using ion sputtering.
  • the base layer may be a single layer or a multilayer.
  • the base layer 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 base layer is equal to or greater than the above lower limit, the adhesion of the surface treatment layer to the base layer will be further improved, and the wear resistance of the surface treatment layer will be more excellent. If the thickness of the base layer is below the above upper limit, the base layer itself will have excellent wear resistance.
  • the thickness of the base layer is measured by observing a cross section of the base layer using a transmission electron microscope (TEM).
  • TEM transmission electron microscope
  • the base layer can be formed, for example, by a vapor deposition method using a vapor deposition material or a wet coating method.
  • the vapor deposition material used in the vapor deposition method preferably contains an oxide containing silicon and a specific element.
  • Specific examples of the form of the vapor deposition material include powder, molten body, sintered body, granulated body, and crushed body, and from the viewpoint of ease of handling, molten body, sintered body, and granulated body are preferable.
  • the melt means a solid obtained by melting the powder of the vapor deposition material at a high temperature and then cooling and solidifying the powder.
  • a sintered body means a solid obtained by firing a powder of a vapor deposition material, and if necessary, a molded body obtained by press-molding the powder may be used instead of a powder of a vapor deposition material.
  • the granule refers to a solid material obtained by kneading a powder of a vapor deposition material and a liquid medium (for example, water, an organic solvent) to obtain particles, and then drying the particles.
  • the vapor deposition material can be manufactured, for example, by the following method.
  • ⁇ Powders containing silicon e.g. powder of silicon oxide, silica sand, silica gel
  • powders containing specific elements e.g.
  • ⁇ Powders containing silicon e.g. powder of silicon oxide, silica sand, silica gel
  • powders containing specific elements e.g. powder of oxides of specific elements, carbonates, sulfates, nitrates, oxalic acid
  • a specific example of a vapor deposition method using a vapor deposition material includes a vacuum vapor deposition method.
  • the vacuum deposition method is a method in which a deposition material is evaporated in a vacuum chamber and adhered to the surface of a base material.
  • the temperature during vapor deposition (for example, the temperature of the boat in which the vapor deposition material is placed when using a vacuum vapor deposition apparatus) is preferably 100 to 3,000°C, more preferably 500 to 3,000°C.
  • the pressure during vapor deposition (for example, when using a vacuum vapor deposition apparatus, the pressure in the tank in which the vapor deposition material is placed) is preferably 1 Pa or less, more preferably 0.1 Pa or less.
  • one vapor deposition material may be used, or two or more vapor deposition materials containing different elements may be used.
  • evaporation methods include resistance heating, in which the evaporation material is melted and evaporated on a resistance heating boat made of high-melting-point metal, and irradiation of an electron beam onto the evaporation material to directly heat the evaporation material on the surface.
  • An example is the electron gun method, which melts and evaporates.
  • the method of evaporating the deposition material is that it can evaporate high-melting point substances because it can be heated locally, and that there is no risk of reaction with the container or contamination with impurities because the area that is not hit by the electron beam is at a low temperature. Gun law is preferred.
  • a plurality of boats may be used, or all the evaporation materials may be placed in a single boat.
  • the vapor deposition method may be codeposition, alternate vapor deposition, or the like. Specifically, examples include mixing silica and a specific element source in the same boat, co-evaporating silica and a specific element source in separate boats, and alternately depositing silica and a specific element source in separate boats. can be mentioned.
  • the conditions, order, etc. of vapor deposition are appropriately selected depending on the structure of the underlying layer.
  • the base layer on the base material by a wet coating method using a coating liquid containing a compound containing silicon, a compound containing a specific element, and a liquid medium.
  • silicon compounds include silicon oxide, silicic acid, partial condensates of silicic acid, alkoxysilanes, and partially hydrolyzed condensates of alkoxysilanes.
  • Specific examples of compounds containing specific elements include oxides of specific elements, alkoxides of specific elements, carbonates of specific elements, sulfates of specific elements, nitrates of specific elements, oxalates of specific elements, and water of specific elements. Examples include oxides.
  • liquid medium examples include those similar to the liquid medium contained in the composition of the present disclosure described above.
  • the content of the liquid medium is preferably 0.01 to 20% by mass, more preferably 0.1 to 10% by mass, based on the total amount of the coating liquid used to form the base layer.
  • wet coating methods for forming the base layer include spin coating, wipe coating, spray coating, squeegee coating, dip coating, die coating, inkjet, flow coating, roll coating, Examples include the cast method, Langmuir-Blodgett method, and gravure coating method.
  • the drying temperature of the coating film is preferably 20 to 200°C, more preferably 80 to 160°C.
  • the article of the present disclosure is preferably an optical member.
  • optical components include medical devices such as car navigation systems, mobile phones, smartphones, digital cameras, digital video cameras, PDAs, portable audio players, car audio, game devices, eyeglass lenses, camera lenses, lens filters, sunglasses, and gastrocameras.
  • medical devices such as car navigation systems, mobile phones, smartphones, digital cameras, digital video cameras, PDAs, portable audio players, car audio, game devices, eyeglass lenses, camera lenses, lens filters, sunglasses, and gastrocameras.
  • Examples include personal appliances, copying machines, PCs, displays (eg, liquid crystal displays, organic EL displays, plasma displays, touch panel displays), touch panels, protective films, and antireflection films.
  • the article is preferably a display or a touch panel.
  • a method for producing an article of the present disclosure is, for example, a method of surface-treating a base material using the surface treatment agent of the present disclosure to produce an article in which a surface-treated layer is formed on the base material.
  • Surface treatments include dry coating methods and wet coating methods.
  • dry coating methods include vacuum deposition, CVD, and sputtering.
  • a vacuum evaporation method is preferable from the viewpoint of suppressing decomposition of the compound and the simplicity of the apparatus.
  • a pellet-like substance obtained by impregnating a porous metal body such as iron or steel with the compound of the present disclosure may be used.
  • a pellet-like material impregnated with the compound of the present disclosure may be used by impregnating a porous metal body such as iron or steel with a composition containing the compound of the present disclosure and a liquid medium, and drying the liquid medium.
  • wet coating methods include spin coating, wipe coating, spray coating, squeegee coating, dip coating, die coating, inkjet coating, flow coating, roll coating, casting, and Langmuir-Blodgett methods. , gravure coating method.
  • an operation may be performed to accelerate the reaction between the compound of the present disclosure and the base material, if necessary.
  • Such operations include heating, humidification, light irradiation, and the like.
  • a hydrolysis reaction of hydrolyzable groups, a reaction between hydroxyl groups, etc. on the surface of the base material and silanol groups, and a condensation reaction of silanol groups. can promote reactions such as the formation of siloxane bonds.
  • compounds in the surface treatment layer that are not chemically bonded to other compounds or the base material may be removed as necessary. Examples of the removal method include a method of pouring a solvent onto the surface treatment layer, a method of wiping with a cloth impregnated with a solvent, and the like.
  • Example 1 Synthesis of compound (1-2)] Using 58 g (1 mol) of propylene glycol as an initiator, 580 g (10 mol) of propylene oxide is polymerized in the presence of potassium hydroxide, and then 440 g (10 mol) of ethylene oxide is polymerized, neutralized, and the neutralized salt is removed. As a result, a compound (1-1) having a number average molecular weight of about 1,100 was obtained.
  • Compound (1-1) was a compound having two specific polyalkylene oxide chains in which five RO units and five EO units were bonded in blocks.
  • Example 2 Synthesis of compound (2-2)] Using 92 g (1 mol) of glycerin as an initiator, polymerize 870 g (15 mol) of propylene oxide in the presence of potassium hydroxide, then polymerize 660 g (15 mol) of ethylene oxide, neutralize and remove the neutralized salt. Compound (2-1) having a number average molecular weight of 1,600 was obtained. Compound (2-1) was a compound having three specific polyalkylene oxide chains in which five RO units and five EO units were connected in blocks.
  • Example 3 Synthesis of compound (3-2)] 16.2 g (10 mmol) of the compound (2-1) and 2.0 g (10 mmol) of trimethoxysilylpropyl isocyanate (manufactured by Tokyo Kasei Co., Ltd.) were added to a 300 mL eggplant-shaped flask. Subsequently, 0.18 g (1.8 mmol) of 1% by mass triethylamine was added to the obtained mixture, and the mixture was stirred at 80° C. for 16 hours.
  • trimethoxysilylpropyl isocyanate manufactured by Tokyo Kasei Co., Ltd.
  • Example 4 Synthesis of compound (4-2)]
  • 16.2 g (10 mmol) of the compound (2-1) 7-(3-isocyanatopropyl)-3,3,11,11-tetramethoxy-7-(3-(trimethoxy 6.0 g (10 mmol) of silyl)propyl)-2,12-dioxa-3,7,11-trisilatridecane was added.
  • 2.2 g (2.2 mmol) of 1% by mass triethylamine was added to the obtained mixture, and then stirred at 80° C. for 16 hours.
  • Example 5 Synthesis of compound (5-2)]
  • 16.2 g (10 mmol) of the compound (2-1) 7-(3-isocyanatopropyl)-3,3,11,11-tetramethoxy-7-(3-(trimethoxy 12.0 g (20 mmol) of silyl)propyl)-2,12-dioxa-3,7,11-trisilatridecane was added.
  • 3.8 g (3.8 mmol) of 1% by mass triethylamine was added to the obtained mixture, and then stirred at 80° C. for 16 hours.
  • Example 6 Synthesis of compound (C1-1)] Using 58 g (1 mol) of propylene glycol as an initiator, 880 g (20 mol) of ethylene oxide is polymerized in the presence of potassium hydroxide, followed by neutralization and removal of the neutralized salt, resulting in a number average molecular weight of about 940. Compound (C1-1) was obtained. Compound (C1-1) was a compound having two polyalkylene oxide chains each consisting of 10 EO units.
  • Example 7 Synthesis of compound (C2-2)] Using 92 g (1 mol) of glycerin as an initiator, 1320 g (30 mol) of ethylene oxide was polymerized in the presence of potassium hydroxide, and then neutralized and the neutralized salt was removed to obtain compound (C2-1).
  • Compound (C2-1) was a compound having three polyalkylene oxide chains each consisting of 10 EO units.
  • Example 8 Compound (C3-1)] The compound (C1-1) was used as it was to prepare a compound (C3-1).
  • Example 9 Synthesis of compound (C4-2)] After polymerizing 1,160 g (20 mol) of propylene oxide in the presence of potassium hydroxide using 58 g (1 mol) of propylene glycol as an initiator, neutralization and removal of the neutralized salt resulted in a number average molecular weight of approx. A compound (C4-1) having a molecular weight of 1,200 was obtained. Compound (C4-1) was a compound having two polyalkylene oxide chains each consisting of 10 RO units.
  • Example 10 Synthesis of compound (C5-2)] After polymerizing 1,740 g (30 mol) of propylene oxide in the presence of potassium hydroxide using 92 g (1 mol) of glycerin as an initiator, neutralization and removal of the neutralized salt resulted in a number average molecular weight of 1,800. Compound (C5-1) was obtained. Compound (C5-1) was a compound having three polyalkylene oxide chains each consisting of 10 RO units.
  • Example 11 Compound (C6-1)] Hydroxy(polyethylene oxide)propyltriethoxysilane (manufactured by Azumax Co., Ltd.) was used as it was to prepare compound (C6-1). HO(CH 2 CH 2 O) 8-12 -(CH 2 ) 3 -Si(OC 2 H 5 ) 3 (C6-1)
  • a composition for forming a surface layer (that is, a surface treatment agent) was prepared using each compound obtained in Examples 1 to 11. Specifically, each compound obtained in Examples 1 to 11 was added to a solvent in which propylene glycol monomethyl ether, diacetone alcohol, and 0.1% by mass nitric acid aqueous solution were mixed at a mass ratio of 51:9:40, and the solid content concentration was adjusted. The mixture was added in an amount of 10% by mass and stirred at 50° C. for 16 hours to obtain a liquid composition containing a partially hydrolyzed condensate of the compound. Further, this liquid composition was dissolved in a mixed solvent of propylene glycol monomethyl ether and diacetone alcohol at a ratio of 85:15 (mass ratio) so that the solid content concentration was 1.0% by mass. It was made into a composition.
  • a composition for forming a surface layer prepared using each compound obtained in Examples 1 to 11 was applied by dip coating onto the surface of a cleaned glass plate measuring 23 mm in length, 25 mm in width, and 3 mm in thickness. A coating was formed on the object. Next, this was dried in a hot air circulation oven at 150°C for 1 hour to form a surface treatment layer with a thickness of 1.8 nm, to obtain glass substrates with surface treatment layers, which are the articles of Examples 1 to 11. . Further, a washed glass plate having a length of 23 mm, a width of 25 mm, and a thickness of 3 mm was used as it was to prepare an article of Example 12. The obtained article was evaluated by the following method. The results are shown in Table 1.
  • the initial contact angle of water was measured on the surfaces of the surface treatment layers of the articles of Examples 1 to 11 and the surface of the glass plate of Example 12. Specifically, the contact angle of about 2 ⁇ L of distilled water placed on the surface was measured using a contact angle measuring device (DM-500, manufactured by Kyowa Interface Science Co., Ltd.). The smaller the initial water contact angle, the higher the hydrophilicity.
  • ⁇ Abrasion resistance (steel wool)>
  • the surface of the surface treatment layer in the articles of Examples 1 to 11 and the surface of the glass plate of Example 12 were tested using an abrasion tester ("HEIDON-14DR (product name)” manufactured by Shinto Kagaku) and coated with steel wool Bonstar (#0000).
  • HEIDON-14DR product name
  • steel wool Bonstar #0000
  • an artificial fingerprint liquid was applied with an artificial finger as described in the fingerprint visibility evaluation above, and then the surface was subjected to an abrasion test.
  • a machine (“HEIDON-14DR (product name)” manufactured by Shinto Kagaku)
  • steel wool Bonstar (#0000) was moved back and forth 10 times at a pressure of 25 kPa and a speed of 320 cm/min, and then 3 times with a wet tissue. Visibility after wiping and rubbing was visually confirmed.
  • the evaluation criteria are the same as those for the initial visibility evaluation.
  • Examples 1 to 5 are examples, and Examples 6 to 12 are comparative examples.
  • the contact angle of water at the initial stage is small, so the hydrophilicity is high, and the visibility of fingerprints at the initial stage is reduced, and the value of the contact angle after rubbing is lower than that at the initial stage. The value is close to that of the contact angle, and the visibility of fingerprints is reduced even after rubbing.
  • Examples 1 to 5 both the property of reducing fingerprint visibility and the abrasion resistance are good.
  • Examples 6 to 12 cannot achieve both the property of reducing fingerprint visibility and the excellent abrasion resistance.
  • Sb the contact angle of water at the initial stage was large and the hydrophilicity was insufficient, and the reduction in fingerprint visibility was insufficient.
  • the compounds of the present disclosure are useful as surface treatment agents.
  • the surface treatment agent can be used, for example, for substrates in display devices such as touch panel displays, optical elements, semiconductor elements, building materials, automobile parts, nanoimprint technology, and the like.
  • the surface treatment agent can be used for bodies, window glasses (windshields, side glasses, rear glasses), mirrors, bumpers, etc. of transportation equipment such as trains, automobiles, ships, and airplanes.
  • the surface treatment agent can be used for outdoor articles such as building exterior walls, tents, solar power generation modules, sound insulation boards, and concrete; fishing nets, insect nets, and aquariums.
  • the surface treatment agent can be used for various indoor equipment such as kitchens, bathrooms, washstands, mirrors, toilet peripheral parts; ceramics such as chandeliers and tiles; artificial marble, and air conditioners.
  • the surface treatment agent can be used as an antifouling treatment for jigs, inner walls, piping, etc. in a factory.
  • the surface treatment agent can be used for goggles, glasses, helmets, pachinko machines, textiles, umbrellas, play equipment, and soccer balls.
  • the surface treatment agent can also be used as an adhesion prevention agent for various packaging materials such as food packaging materials, cosmetic packaging materials, and the inside of pots.
  • surface treatment agents are used for medical applications such as car navigation systems, mobile phones, smartphones, digital cameras, digital video cameras, PDAs, portable audio players, car audio, game equipment, eyeglass lenses, camera lenses, lens filters, sunglasses, and gastrocameras. It can be used for optical members such as appliances, copying machines, PCs, displays (for example, liquid crystal displays, organic EL displays, plasma displays, touch panel displays), touch panels, protective films, and antireflection films.
  • medical applications such as car navigation systems, mobile phones, smartphones, digital cameras, digital video cameras, PDAs, portable audio players, car audio, game equipment, eyeglass lenses, camera lenses, lens filters, sunglasses, and gastrocameras.
  • optical members such as appliances, copying machines, PCs, displays (for example, liquid crystal displays, organic EL displays, plasma displays, touch panel displays), touch panels, protective films, and antireflection films.

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  • General Chemical & Material Sciences (AREA)
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Abstract

L'invention concerne un composé ayant : un groupe silyle réactif ; une unité d'oxyde d'éthylène ; une unité d'oxyde d'alkylène en C3-C6 ; et un groupe hydroxy lié à un atome de carbone. Lorsque le nombre de moles de l'unité d'oxyde d'alkylène en C3-C6, et le nombre de moles de l'unité d'oxyde d'éthylène, qui sont contenues dans le composé sont respectivement représentés comme Ma et Mb, le ratio de Ma par rapport à la somme de Ma et de Mb, Ma/(Ma+Mb), est de 0,2 à 0,8. L'invention concerne également : une composition et un agent de traitement de surface comprenant chacun le composé ; et un article et un procédé de production d'un article à l'aide de l'agent de traitement de surface.
PCT/JP2023/015681 2022-04-26 2023-04-19 Composé, composition, agent de traitement de surface, procédé de production d'article et article WO2023210470A1 (fr)

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