WO2023218889A1 - Composition, composé, agent de traitement de surface, et article ainsi que procédé de fabrication de celui-ci - Google Patents

Composition, composé, agent de traitement de surface, et article ainsi que procédé de fabrication de celui-ci Download PDF

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WO2023218889A1
WO2023218889A1 PCT/JP2023/015687 JP2023015687W WO2023218889A1 WO 2023218889 A1 WO2023218889 A1 WO 2023218889A1 JP 2023015687 W JP2023015687 W JP 2023015687W WO 2023218889 A1 WO2023218889 A1 WO 2023218889A1
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group
integer
compound
carbon atoms
silsesquioxane
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雄二郎 富塚
啓吾 松浦
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Ａｇｃ株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
    • C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/14—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/18—Coatings for keeping optical surfaces clean, e.g. hydrophobic or photo-catalytic films

Definitions

  • Means for solving the above problems include the following aspects. ⁇ 1> A silsesquioxane skeleton, a hydroxyl group bonded directly to the silicon atom of the silsesquioxane skeleton or via an alkylene group, and a hydroxyl group bonded to the silicon atom of the silsesquioxane skeleton through a trivalent or higher valent linking group. at least one selected from the group consisting of a silsesquioxane compound, a hydrolyzate thereof, and a partial condensate thereof, and a plurality of reactive silyl groups bonded together; water and, A solvent other than water, acid or alkali; A composition comprising.
  • ⁇ 3> The composition according to ⁇ 1> or ⁇ 2>, wherein the silsesquioxane skeleton is a cage-shaped silsesquioxane skeleton.
  • ⁇ 4> The composition according to ⁇ 2>, wherein the ratio of m1 to m2 in the silsesquioxane compound is 1:7 to 7:1.
  • ⁇ 5> The composition according to any one of ⁇ 1> to ⁇ 4>, wherein the acid or alkali is an alkali.
  • ⁇ 6> The composition according to ⁇ 5>, wherein the alkali is an ammonium compound.
  • ⁇ 7> The composition according to any one of ⁇ 1> to ⁇ 6>, wherein the solvent is alcohol.
  • the silsesquioxane compound contains a plurality of reactive silyl groups bonded to the silicon atom of the silsesquioxane skeleton via a trivalent or higher valent linking group.
  • the number of reactive silyl groups bonded to one silicon atom of the silsesquioxane skeleton is preferably 2 to 15, more preferably 2 to 9, and even more preferably 2 or 3.
  • the number of reactive silyl groups in one molecule of the silsesquioxane compound is preferably 2 to 60, more preferably 2 to 36, even more preferably 2 to 12, particularly preferably 2 to 9, and most preferably 2 or 3. .
  • the structures of the plurality of reactive silyl groups may be the same or different from each other.
  • 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.
  • R is each independently a monovalent hydrocarbon group
  • L is each independently a hydrolyzable group or a hydroxyl group
  • n is an integer from 0 to 2.
  • the plurality of groups (2) may be the same or different. From the viewpoint of excellent availability of raw materials and ease of manufacturing the compound, it is preferable that the plurality of groups (2) are the same.
  • the silicon atom of the silsesquioxane skeleton has a hydroxyl group directly or via an alkylene group, or a plurality of reactive groups bonded to the silicon atom of the silsesquioxane skeleton via a trivalent or higher valent linking group. Only “silyl group” may be bonded.
  • the silsesquioxane compound is preferably a compound represented by the following formula (1) from the viewpoint of excellent scratch resistance and abrasion resistance.
  • SQ 8 (Y 1 [Si(R) n L 3-n ] g ) m1 [(CH 2 ) n1 OH] m2 (R x ) m3 ...(1)
  • SQ 8 is a silsesquioxane skeleton having 8 Si atoms
  • Y 1 is each independently a (g+1)-valent linking group
  • R is each independently a monovalent hydrocarbon group
  • L is each independently a hydrolyzable group or a hydroxyl group
  • n is each independently an integer from 0 to 2
  • g is each independently an integer of 1 or more, at least one g is an integer of 2 or more
  • m1 is an integer from 1 to 7
  • m2 is an integer from 1 to 7
  • m3 is an integer from 0 to 6
  • each g is independently an integer of 1 or more, and at least one g is an integer of 2 or more.
  • g is each independently preferably an integer of 2 to 15, more preferably an integer of 2 to 9, even more preferably 2 or 3.
  • the total g in compound (1) is preferably 2 to 60, more preferably 2 to 36, even more preferably 2 to 12, particularly preferably 2 to 9, and most preferably 2 or 3.
  • the ratio of m1 to m2 in the silsesquioxane compound is preferably 1:7 to 7:1, may be 2:6 to 6:2, or may be 3:5 to 5:3.
  • the above-mentioned "ratio of m1 and m2 in the silsesquioxane compound" refers to (Number of silicon atoms in the silsesquioxane skeleton): (Number of silicon atoms in the silsesquioxane skeleton bonded to the reactive silyl group).
  • the hydrocarbon group may be substituted with a halogen atom (for example, a fluorine atom), and from the viewpoint of reducing environmental load, it is preferable that it is not substituted with a halogen atom (for example, a fluorine atom).
  • a halogen atom for example, a fluorine atom
  • the alkoxy group include groups in which an oxygen atom is bonded to the group exemplified as the hydrocarbon group. However, the oxygen atom is bonded to the silicon atom in SQ8 .
  • 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, L, 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.
  • the SQ 8 end of Q a is not -S-, -SO 2 -, -N(R d )-, -C(O)-, or -Si(R a ) 2 -.
  • R a is an alkyl group (preferably having 1 to 10 carbon atoms) or a phenyl group.
  • 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 hetero atoms constituting the ring are preferably nitrogen atoms, oxygen atoms, and sulfur atoms, and more preferably nitrogen atoms and oxygen atoms.
  • 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.
  • rings include the rings shown below, 1,3-cyclohexadiene ring, 1,4-cyclohexadiene ring, anthracene ring, cyclopropane ring, decahydronaphthalene ring, norbornene ring, norbornadiene ring, 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.
  • the remaining bonds, if any, are bonded to hydrogen atoms or substituents.
  • any two of Q a , (-Q b -Si(R) n L 3-n ), and -R 31 may be bonded to that one carbon atom.
  • 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 abrasion resistance of the surface treatment layer. is preferable, and a carbon atom or a silicon 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.
  • R a is an alkyl group (preferably having 1 to 10 carbon atoms) or a phenyl group.
  • R d is a hydrogen atom or an alkyl group (preferably having 1 to 10 carbon atoms).
  • Examples of the divalent hydrocarbon group include a divalent saturated hydrocarbon group, a divalent aromatic hydrocarbon group, an alkenylene group, and an alkynylene group.
  • the divalent saturated hydrocarbon group may be linear, branched, or cyclic, and includes, for example, an alkylene group.
  • the carbon number of the divalent saturated hydrocarbon group (e.g. alkylene group) is preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, and examples include 2, 3, 8, 9, and 11. .
  • the alkynylene group or alkenylene group preferably has 2 to 20 carbon atoms, and examples thereof include 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.
  • groups combining two or more of the above include -OC(O)-, -C(O)O-, -C(O)N(R d )-, -N(R d )C(O )-, -N(R d )C(O)N(R d )-, -N(R d )C(O)O-, -OC(O)N(R d )-, -SO 2 N( R d )-, -N(R d )SO 2 -, -C(O)N(R d )-, alkylene group having -N(R d )C(O)-, etheric oxygen an alkylene group having an atom, an alkylene group having -OC(O)-, an alkylene group having -C(O)O-, an alkylene group having -
  • 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 (-R 31 )s may be the same or different.
  • 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 a hydrogen atom is preferable from the viewpoint of easy production of the compound.
  • y is an integer of 1 to 10, preferably an integer of 1 to 6.
  • Two or more [CH 2 C(R 32 )(-Q d -Si(R) n L 3-n )] may be the same or different.
  • groups (3-1A-1) to (3-1A-7) are preferable.
  • -(O) s1 -Q b1 -Si(R) n L 3-n ...(3-1A-1) -(O) s2 -Q a2 -N [-Q b2 -Si(R) n L 3-n ] 2 ...(3-1A-2) -Q a3 -Si(R g ) [-Q b3 -Si(R) n L 3-n ] 2 ...(3-1A-3) -[O] s4 -Q a4 -(O) t4 -C[-(O) u4 -Q b4 -Si(R) n L 3-n ] 3-w1 (-R 31 ) w1 ...(3-1A- 4) -Q a5 -Si [-Q b5 -Si(R) n L 3-n ] 3 ...
  • 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.
  • the alkylene group has -O-, a silphenylene skeleton group, a divalent organopolysiloxane residue, or a dialkylsilylene group
  • the number of carbon atoms in the alkylene group represented by Q b1 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.
  • group (3-1A-1) include the following groups.
  • * represents the bonding position of SQ 8 to the silicon atom.
  • Q a2 is a single bond, an alkylene group, -C(O)-, or an etheric oxygen atom between carbon atoms of an alkylene group having 2 or more carbon atoms, - C(O)-, -C(O)O-, -OC(O)-, -C(O)N(R d )-, -N(R d )C(O)-, -N(R d )C(O)N(R d )-, -N(R d )C(O)O-, -OC(O)N(R d )-, -SO 2 N(R d )-, -N( R d ) is a group having SO 2 -, -C(O)N(R d )-, or -NH-.
  • the alkylene group represented by Q a2 preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, even more preferably 1 to 6 carbon atoms, and particularly preferably 1 to 3 carbon atoms.
  • 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 Q a2 is a single bond, it is 0).
  • 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.
  • group (3-1A-2) include the following groups.
  • * represents the bonding position of SQ 8 to the silicon atom.
  • ⁇ 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, ⁇ 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, or 11. The same applies below.
  • Q a3 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 20 carbon atoms, more preferably 1 to 10 carbon atoms, even more preferably 1 to 6 carbon atoms, and particularly preferably 1 to 3 carbon atoms. Further, the number of carbon atoms may be 2 to 6.
  • 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) n L 3-n ] may be the same or different.
  • group (3-1A-3) include the following groups.
  • * represents the bonding position of SQ 8 to the silicon atom.
  • r represents an integer from 1 to 10.
  • 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 ether oxygen atom.
  • the alkylene group which may have an etheric oxygen atom preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, even more preferably 1 to 6 carbon atoms, and particularly preferably 1 to 3 carbon atoms. Further, the number of carbon atoms may be 2 to 6.
  • t4 is 0 or 1 (however, when Q a4 is a single bond, it is 0).
  • -Q a4 -(O) t4 - is -CH 2 O-, -CH 2 OCH 2 -, -CH 2 OCH 2 CH 2 O-, -CH 2 OCH 2 CH 2 OCH 2 -, -CH 2 OCH 2 CH 2 CH 2 OCH 2 - are preferred (however, the left side is bonded to the silicon atom of SQ 8 ), and when s4 is 1, A single bond, -CH 2 -, and -CH 2 CH 2 - are preferred.
  • 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 may 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.
  • 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) n L 3-n ], two or more [-(O) u4 -Q b4 -Si(R) n L 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 of SQ 8 to the silicon atom.
  • r represents an integer from 0 to 10.
  • Q a5 is an alkylene group or a (poly)oxyalkylene group which may have an etheric oxygen atom.
  • the alkylene group which may have an etheric oxygen atom preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, even more preferably 1 to 6 carbon atoms, and particularly preferably 1 to 3 carbon atoms. Further, the number of carbon atoms may be 2 to 6.
  • Q a5 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 - and OCH 2 CH 2 CH 2 - are preferred (however, the right side is bonded to Si).
  • Q b5 is a single bond, 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. From the viewpoint of easy production of the compound, 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) n L 3- bond to n ).
  • the three [-Q b5 -Si(R) n L 3-n ] may be the same or different.
  • group (3-1A-5) include the following groups.
  • * represents the bonding position of SQ 8 to the silicon atom.
  • r represents an integer from 1 to 10.
  • v is 0 or 1.
  • Q a6 is an alkylene group which may have an etheric oxygen atom.
  • the alkylene group which may have an etheric oxygen atom preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, even more preferably 1 to 6 carbon atoms, and particularly preferably 1 to 3 carbon atoms. Further, the number of carbon atoms may be 2 to 6. From the viewpoint of easy production of the compound, Q a6 includes -CH 2 OCH 2 CH 2 CH 2 -, -CH 2 OCH 2 CH 2 OCH 2 CH 2 CH 2 -, -CH 2 CH 2 - , and -CH 2 CH 2 CH 2 - is preferred (provided that the right side is bonded to Z a ).
  • Z a is a (w+1)-valent organopolysiloxane residue.
  • w2 is an integer from 2 to 7.
  • Examples of the (w2+1)-valent organopolysiloxane residue include the following groups. However, 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) n3 L 3-n ] may be the same or different.
  • group (3-1A-6) include the following groups.
  • * represents the bonding position of SQ 8 to the silicon atom.
  • r represents an integer from 1 to 10.
  • 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 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) n L 3-n ] may be the same or different.
  • group (3-1A-7) include the following groups.
  • * represents the bonding position of SQ 8 to the silicon atom.
  • r represents an integer from 0 to 10.
  • Y 1 in formula (1) may be groups (g2-1) to (g2-7).
  • the A 1 side is connected to the silicon atom of SQ 8 , and the Q 22 , Q 23 , Q 24 , Q 25 or Q 26 side is [-Si(R) n L 3-n ].
  • a 1 is a single bond or -O-.
  • 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 is a single bond, an alkylene group, or a combination of an alkylene group having 2 or more carbon atoms and -C(O)NR 6 -, -C(O)-, -NR 6 - or -O-.
  • Q 13 is a single bond, an alkylene group, or a combination of an alkylene group having 2 or more carbon atoms and -C(O)NR 6 -, -C(O)-, -NR 6 - or -O-.
  • 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 is an alkylene group or a combination of an alkylene group and -C(O)NR 6 -, -C(O)-, -NR 6 - or -O-.
  • 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 two or more
  • 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 is Q 23 when the atom in Z 1 to which Q 24 is bonded is a nitrogen atom, and two or more Q 24 exist. In this case, two or more Q24 's 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; , Q 25 exists, two or more Q 25 may be the same or different.
  • Q 26 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. .
  • Z 1 is a group having a (h2+1)-valent ring structure in which Q 14 has a carbon atom or nitrogen atom to which Q 14 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 two or more R e1s exist, 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.
  • d2 is an integer of 0 to 2, preferably 1 or 2.
  • d4 is an integer from 0 to 3, preferably 2 or 3.
  • d2+d4 is an integer from 1 to 5, preferably 4 or 5.
  • e2 is an integer from 1 to 3, preferably 2 or 3.
  • h2 is an integer of 1 or more, preferably 2 or 3.
  • 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 excellent manufacturing ease of the compound and the surface treatment layer. From the viewpoint of even better wear resistance, the number is preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, may be 2 to 10, and 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 from 1 to 6, more preferably from 1 to 3, even more preferably from 1 to 2, from the viewpoint of excellent ease of manufacturing the compound.
  • the number of carbon atoms in the alkyl group portion of the acyloxy group of R e2 is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2 from the viewpoint of excellent ease of manufacturing the compound.
  • h2 is preferably 2 to 6, more preferably 2 to 4, and even more preferably 2 or 3, from the viewpoint of excellent ease of manufacturing the compound and further excellent wear resistance of the surface treatment layer.
  • Y 1 in formula (1) may be groups (g2-8) to (g2-14).
  • the A 1 side is connected to the silicon atom of SQ 8 , and the G 1 side is connected to [-Si(R) n L 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) n L 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.
  • k3 is 2 or 3.
  • R 6 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.
  • R 9 is an alkyl group, a phenyl group, or an alkoxy group, and two R 9s may be the same or different.
  • p is an integer 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 number of carbon atoms in the alkylene group of Q 3 is preferably 1 to 30, more preferably 1 to 20, more preferably 2 to 20, from the viewpoint of excellent ease of manufacturing the compound and from the viewpoint of further excellent wear resistance of the surface treatment layer. is more preferable, and 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, 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 excellent ease of manufacturing the compound.
  • the number of carbon atoms in the alkyl group of R 9 is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2 from the viewpoint of excellent ease of manufacturing the compound.
  • the number of carbon atoms in the alkoxy group of R 9 is preferably 1 to 6, more preferably 1 to 3, and 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 compound (1) include a compound (1) having the following Y 1 [Si(R) n L 3-n ] g .
  • Examples of Y 1 [Si(R) n L 3-n ] g in which Y 1 is a group (g2-1) include the following structures.
  • Examples of Y 1 [Si(R) n L 3-n ] g in which Y 1 is a group (g2-2) include the following structures.
  • Examples of Y 1 [Si(R) n L 3-n ] g in which Y 1 is a group (g2-3) include the following structures.
  • Examples of Y 1 [Si(R) n L 3-n ] g in which Y 1 is a group (g2-4) include the following structures. r represents an integer from 0 to 10.
  • Examples of Y 1 [Si(R) n L 3-n ] g in which Y 1 is a group (g2-5) include the following structures.
  • Examples of Y 1 [Si(R) n L 3-n ] g in which Y 1 is a group (g2-6) include the following structures.
  • Examples of Y 1 [Si(R) n L 3-n ] g in which Y 1 is a group (g2-7) include the following structures.
  • Examples of Y 1 [Si(R) n L 3-n ] g in which Y 1 is a group (g2-8) include the following structures.
  • Examples of Y 1 [Si(R) n L 3-n ] g in which Y 1 is a group (g2-9) include the following structures.
  • Examples of Y 1 [Si(R) n L 3-n ] g in which Y 1 is a group (g2-10) include the following structures.
  • Examples of Y 1 [Si(R) n L 3-n ] g in which Y 1 is a group (g2-11) include the following structures.
  • Examples of Y 1 [Si(R) n L 3-n ] g in which Y 1 is a group (g2-13) include the following structures.
  • Examples of Y 1 [Si(R) n L 3-n ] g in which Y 1 is a group (g2-14) include the following structures.
  • silsesquioxane compound for example, the following compounds are preferred.
  • the definition and details of the monovalent hydrocarbon group are the same as the definition and details of the monovalent hydrocarbon group in formula (1).
  • the details of the silsesquioxane compound described above can be applied, except that the silsesquioxane skeleton is a complete cage-type silsesquioxane skeleton.
  • Examples of the cissesquioxane compound include compounds (3) and (4) in addition to compound (1).
  • the number of Si carbon atoms in SQ 10 and SQ 12 of compounds (3) and (4) is 10 and 12, respectively.
  • SQ 10 and SQ 12 of compounds (3) and (4) are preferably cage-shaped.
  • SQ 12 (Y 1 [Si(R) n L 3-n ] g ) m1 [(CH 2 ) n1 OH] m2 (R x ) m3 ...(4)
  • SQ 12 is a silsesquioxane skeleton having 12 Si atoms
  • Y 1 is each independently a (g+1)-valent linking group
  • R is each independently a monovalent hydrocarbon group
  • L is each independently a hydrolyzable group or a hydroxyl group
  • n is each independently an integer from 0 to 2
  • g is each independently an integer of 1 or more, at least one g is an integer of 2 or more
  • m1 is an integer from 1 to 11
  • m2 is an integer from 1 to 11
  • m3 is an integer from 0 to 10
  • n1 is an integer from 0 to 5
  • R x is a monovalent organic group
  • Y 1 , (CH 2 ) n1 , and R x each bond
  • each symbol in formula (3) is as follows, except that SQ 10 is silsesquioxane having 10 Si atoms and m1+m2+m3 is 10. Same as details.
  • the ratio of m1 and m2 in formula (3) is preferably 1:9 to 9:1.
  • the specific embodiment of formula (3) is the same as the specific embodiment of formula (1) except for the above.
  • each symbol in formula (4) is as follows, except that SQ 12 is silsesquioxane having 12 Si atoms and m1+m2+m3 is 12. Same as details.
  • the ratio of m1 and m2 in formula (4) is preferably 1:11 to 11:1.
  • the specific embodiment of formula (4) is the same as the specific embodiment of formula (1) except for the above.
  • SQ 8 [Y 11 (B) g1 ] m1 [(CH 2 ) n1 OH] m2 (R x ) m3 ...(1-1)
  • SQ 8 is a silsesquioxane skeleton having 8 Si atoms
  • Y 11 is each independently a (g1+1)-valent linking group
  • g1 is each independently an integer of 1 or more, at least one g1 is an integer of 2 or more, m1 is an integer from 1 to 7, m2 is an integer from 1 to 7, m3 is an integer from 0 to 6, m1+m2+m3 is 8,
  • R x is a monovalent organic group
  • Y 11 (CH 2 ) n1 , and R x each bond to the silicon atom in SQ 8 .
  • SQ 10 [Y 11 (B) g1 ] m1 [(CH 2 ) n1 OH] m2 (R x ) m3 ...(3-1)
  • SQ 10 is a silsesquioxane skeleton having 10 Si atoms
  • Y 11 is each independently a (g1+1)-valent linking group
  • g1 is each independently an integer of 1 or more, at least one g1 is an integer of 2 or more, m1 is an integer from 1 to 9, m2 is an integer from 1 to 9, m3 is an integer from 0 to 8, m1+m2+m3 is 10, n1 is an integer from 0 to 5,
  • R x is a monovalent organic group
  • Y 11 (CH 2 ) n1 , and R x each bond to the silicon atom in SQ 10 .
  • SQ 12 is a silsesquioxane skeleton having 12 Si atoms
  • Y 11 is each independently a (g1+1)-valent linking group
  • Q L is a single bond or a divalent linking group
  • g1 is each independently an integer of 1 or more, at least one g1 is an integer of 2 or more
  • m1 is an integer from 1 to 11
  • m2 is an integer from 1 to 11
  • m3 is an integer from 0 to 10
  • n1 is an integer from 0 to 5
  • R x is a monovalent organic group
  • Y 11 (CH 2 ) n1
  • R x each bond to the silicon atom in SQ 12 .
  • trifunctional or higher functional alkoxysilanes examples include tetraethoxysilane (TEOS), tetramethoxysilane, n-octyltetraethoxysilane, triethoxymethylsilane, phenyltriethoxysilane, etc., and n-octyltetraethoxysilane and TEOS preferable.
  • TEOS tetraethoxysilane
  • tetramethoxysilane tetramethoxysilane
  • n-octyltetraethoxysilane triethoxymethylsilane
  • phenyltriethoxysilane etc.
  • n-octyltetraethoxysilane and TEOS preferable.
  • the composition of the present disclosure may contain silica particles from the viewpoint of improving film strength, low reflectivity, etc. when a surface treatment layer is formed.
  • silica particles porous silica particles are preferable, and examples thereof include hollow silica particles, mesoporous particles, and the like.
  • the shape of the silica particles is not particularly limited, and examples include powder, sol (colloidal silica), and the like.
  • colloidal silica it may be used as, for example, water-dispersible colloidal silica or organic solvent-dispersible colloidal silica such as alcohol.
  • the surface treatment agent of the present disclosure comprises a composition of the present disclosure. Since the composition of the present disclosure has the above-described structure, a surface treatment layer having excellent water repellency and abrasion resistance can be formed by using a surface treatment agent containing the composition of the present disclosure.
  • the article of the present disclosure includes a base material and a surface treatment layer surface treated with the surface treatment agent.
  • 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 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 surface treatment of the present disclosure disposed on the base layer. It is preferable to include a surface treatment layer whose surface is treated with an agent.
  • 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 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.
  • ⁇ 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.
  • 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.
  • 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.
  • an organic solvent is preferable.
  • 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.
  • 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.
  • 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 treatment methods include spin coating, wipe coating, spray coating, squeegee coating, dip coating, die coating, inkjet, flow coating, roll coating, casting, and Langmuir-Blodgett methods. , gravure coating method.
  • an operation may be performed to accelerate the reaction between the composition 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.
  • SQL 8 represents a cage-shaped silsesquioxane skeleton having eight Si atoms.
  • Compound (III) is a compound in which a CH 2 OH group is bonded to some of the silicon atoms of SQ 8 , and -CH 2 -O-(CH 2 ) 3 -SiCl 3 is bonded to the remaining silicon atoms. .
  • compound (IV) was obtained by distilling off volatile components under reduced pressure.
  • Compound (V) has a CH 2 OH group bonded to some of the silicon atoms of SQ 8 , and -CH 2 -O-(CH 2 ) 3 -Si[-(CH 2 ) 3 -SiCl to the remaining silicon atoms. 3 ] is a compound in which 3 is bonded.
  • Compound (VI) has a CH 2 OH group bonded to some of the silicon atoms of SQ 8 , and -CH 2 -O-(CH 2 ) 3 -Si[-(CH 2 ) 3 -Si to the remaining silicon atoms. It is a compound in which (OCH 3 ) 3 ] 3 is bonded.
  • Example 6 The prepared compositions of Examples 1 to 5 were applied to a glass substrate by spin coating. The glass substrate obtained after heating at 120° C. for 2 hours was evaluated.
  • compound (VI) was deposited on a glass substrate under the following conditions. The vapor deposition was performed using a vacuum vapor deposition apparatus (manufactured by ULVAC, VTR350M) (vacuum vapor deposition method). 0.5 g of a 20% ethyl acetate solution of compound (VI) was filled into a molybdenum boat in a vacuum evaporation apparatus, and the inside of the vacuum evaporation apparatus was evacuated to 1 ⁇ 10 ⁇ 3 Pa or less.
  • the boat containing the compound is heated at a temperature increase rate of 10°C/min or less, and when the deposition rate exceeds 1 nm/sec using a crystal oscillation film thickness meter, the shutter is opened to form a film on the surface of the substrate. started. When the film thickness reached approximately 50 nm, the shutter was closed to complete the film formation on the surface of the substrate.
  • the substrate on which the compound was deposited was heat-treated at 100° C. for 30 minutes to obtain an article having a surface-treated layer on the surface of the substrate.
  • the composition of the present disclosure is useful as a surface treatment agent.
  • 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.
  • 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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  • Silicon Polymers (AREA)

Abstract

L'invention concerne une composition qui contient : au moins un élément choisi dans un groupe constitué d'un composé silsesquioxane, d'un hydrolysat de ce composé et d'un condensat partiel de ce composé ; une eau ; un solvant autre que l'eau ; et un acide ou un alcali. Ledit composé silsesquioxane contient à son tour : un squelette de silsesquioxane ; un groupe hydroxyle lié directement ou par l'intermédiaire d'un groupe alkylène à un atome de silicium dudit squelette de silsesquioxane ; et une pluralité de groupes silyle réactifs liés par l'intermédiaire d'un groupe de liaison de valence supérieure ou égale à 3 à un atome de silicium dudit squelette de silsesquioxane. L'invention concerne également un composé destiné à préparer ledit composé silsesquioxane, un agent de traitement de surface contenant ladite composition, un article mettant en œuvre ledit agent de traitement de surface, et un procédé de fabrication de cet article.
PCT/JP2023/015687 2022-05-13 2023-04-19 Composition, composé, agent de traitement de surface, et article ainsi que procédé de fabrication de celui-ci WO2023218889A1 (fr)

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5710643A (en) * 1980-06-24 1982-01-20 Japan Synthetic Rubber Co Ltd Silicone resin composition
JP2004331647A (ja) * 2003-03-13 2004-11-25 Chisso Corp シルセスキオキサン骨格を有する重合体および化合物
JP2004359933A (ja) * 2003-05-14 2004-12-24 Nagase Chemtex Corp 光素子用封止材
JP2007251121A (ja) * 2006-02-20 2007-09-27 Matsushita Electric Works Ltd 半導体光装置及び透明光学部材
JP2013001813A (ja) * 2011-06-16 2013-01-07 Nitto Denko Corp シリコーン樹脂組成物、封止層、リフレクタおよび光半導体装置
JP2020184010A (ja) * 2019-05-07 2020-11-12 Jsr株式会社 感放射線性組成物、表示装置用絶縁膜、表示装置、表示装置用絶縁膜の形成方法、及びシルセスキオキサン
WO2021060055A1 (fr) * 2019-09-27 2021-04-01 富士フイルム株式会社 Composition pour formation de couche de revêtement dur, film de revêtement dur ainsi que procédé de fabrication de celui-ci, et article contenant ce film de revêtement dur
JP2022152981A (ja) * 2021-03-29 2022-10-12 マツダ株式会社 高分子材料、遮熱材、防曇フィルム及び高分子材料の製造方法

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5710643A (en) * 1980-06-24 1982-01-20 Japan Synthetic Rubber Co Ltd Silicone resin composition
JP2004331647A (ja) * 2003-03-13 2004-11-25 Chisso Corp シルセスキオキサン骨格を有する重合体および化合物
JP2004359933A (ja) * 2003-05-14 2004-12-24 Nagase Chemtex Corp 光素子用封止材
JP2007251121A (ja) * 2006-02-20 2007-09-27 Matsushita Electric Works Ltd 半導体光装置及び透明光学部材
JP2013001813A (ja) * 2011-06-16 2013-01-07 Nitto Denko Corp シリコーン樹脂組成物、封止層、リフレクタおよび光半導体装置
JP2020184010A (ja) * 2019-05-07 2020-11-12 Jsr株式会社 感放射線性組成物、表示装置用絶縁膜、表示装置、表示装置用絶縁膜の形成方法、及びシルセスキオキサン
WO2021060055A1 (fr) * 2019-09-27 2021-04-01 富士フイルム株式会社 Composition pour formation de couche de revêtement dur, film de revêtement dur ainsi que procédé de fabrication de celui-ci, et article contenant ce film de revêtement dur
JP2022152981A (ja) * 2021-03-29 2022-10-12 マツダ株式会社 高分子材料、遮熱材、防曇フィルム及び高分子材料の製造方法

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