Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • 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
• • 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
  • C08L83/04—Polysiloxanes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D183/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
  • C09D183/04—Polysiloxanes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K3/00—Materials not provided for elsewhere
  • C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces

Definitions

• the present disclosure relates to a compound, a composition, a surface treatment agent, a method for producing an article, and an article.
• a specific method known is to perform a surface treatment on the surface of the article using a surface treatment agent.
• Patent Document 1 describes a silane compound having a specific siloxane group that is used in the above-mentioned surface treatment agent.
• an object of one embodiment of the present invention is to provide a novel compound and composition that are useful as a surface treatment agent capable of forming a surface treatment layer having excellent light resistance on a substrate.
• An object of one embodiment of the present invention is to provide a surface treatment agent capable of forming a surface treatment layer having excellent light resistance on a substrate.
• An object of one embodiment of the present invention is to provide a method for producing an article having a surface treatment layer with excellent light resistance, and to provide the article.
• the compound according to [1], wherein the compound represented by formula (1-1) is a compound represented by formula (2) described later, a compound represented by formula (3) described later, or a compound represented by formula (4) described later.
• [3] The compound according to [1], wherein m is an integer of 2 to 600.
• [4] The compound according to [1] or [3], wherein q is an integer of 1 to 4.
• a composition comprising the compound according to any one of [1] to [6] and a liquid medium.
• a surface treatment agent comprising the compound according to any one of [1] to [6].
• a surface treatment agent comprising the compound according to any one of [1] to [6] and a liquid medium.
• a method for producing an article comprising: performing a surface treatment on a substrate using the surface treatment agent according to [8]; and producing an article having a surface treatment layer formed on the substrate.
• An article comprising a substrate and a surface treatment layer disposed on the substrate and surface-treated with the surface treatment agent according to [8].
• the article according to [11] which is an optical member.
• a novel compound and composition useful as a surface treatment agent capable of forming a surface treatment layer having excellent light resistance on a substrate there is provided a surface treatment agent capable of forming a surface treatment layer having excellent light resistance on a substrate.
• a method for producing an article having a surface treatment layer with excellent light resistance, and the article are provided.
• the numerical range indicated using “to” includes the numerical values before and after “to” as the minimum and maximum values, respectively.
• the upper or lower limit of one numerical range may be replaced with the upper or lower limit of another numerical range.
• the upper or lower limit of the numerical range may be replaced with a value shown in the examples.
• the term “surface treatment layer” refers to a layer formed on the surface of a substrate by surface treatment.
• “Me” refers to a methyl group.
• the bonding direction of the divalent groups described in this specification is not limited unless otherwise specified.
• Y when Y is -COO- in a compound represented by the formula "X-Y-Z", Y may be -CO-O- or -O-CO-.
• the above compound may be "X-CO-O-Z" or "X-O-CO-Z”.
• the compound of the present disclosure is a compound represented by formula (1-1) described below or a compound represented by formula (1-2) described below.
• the compound of the present disclosure refers to at least one of the compounds represented by formula (1-1) and formula (1-2).
• the compounds disclosed herein have linking groups with alicyclic structures that may have heteroatoms at specific positions. Although the detailed reasons are unclear, by using such compounds disclosed herein, it is possible to form a surface treatment layer with excellent light resistance.
• T is (R 1 ) 3 Si—, a monovalent cyclic polysiloxane residue, or a monovalent cage polysiloxane residue;
• Each R 1 is independently a hydrocarbon group or a trialkylsilyloxy group;
• Each R2 is independently a hydrocarbon group or a trialkylsilyloxy group;
• A is a (q+1)-valent linking group having an alicyclic structure which may have a heteroatom,
• Each R is independently a hydrocarbon group;
• Each L is independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group;
• m is a number of 0 or more;
• n is independently an integer from 0 to 2, q is an integer of 1 or more.
• T is (R 1 ) 3 Si—, a monovalent cyclic polysiloxane residue, or a monovalent cage-shaped polysiloxane residue.
• Examples of the hydrocarbon group represented by R1 include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. Among them, the hydrocarbon group is preferably an aliphatic hydrocarbon group, and more preferably an alkyl group.
• the alkyl group may be any of a linear alkyl group, a branched alkyl group, and a cyclic alkyl group, but a linear alkyl group is preferred.
• the number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4.
• the hydrocarbon group represented by R1 is more preferably a methyl group, an ethyl group, an n-propyl group, or an n-butyl group, and particularly preferably a methyl group.
• the alkyl group contained in the trialkylsilyloxy group represented by R1 may be any one of a linear alkyl group, a branched alkyl group, and a cyclic alkyl group, but a linear alkyl group is preferred.
• the number of carbon atoms in the alkyl group contained in the trialkylsilyloxy group represented by R1 is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4.
• the alkyl group contained in the trialkylsilyloxy group represented by R1 is more preferably a methyl group, an ethyl group, an n-propyl group, or an n-butyl group, and even more preferably a methyl group.
• a plurality of R 1s may be the same or different from each other, and from the viewpoint of ease of production, they are preferably the same.
• R 1 is preferably a linear alkyl group or a trialkylsilyloxy group in which the alkyl group is a linear alkyl group, more preferably a methyl group, an ethyl group, an n-propyl group, an n-butyl group, or a trimethylsilyloxy group, and further preferably a methyl group or a trimethylsilyloxy group.
• Examples of the group represented by (R 1 ) 3 Si- include a methyldiethylsilyl group, a methylethylpropylsilyl group, a methylethylbutylsilyl group, a methyldipropylsilyl group, a methylpropylbutylsilyl group, a methyldibutylsilyl group, a dimethylethylsilyl group, a dimethylpropylsilyl group, a dimethylbutylsilyl group, a trimethylsilyl group, a triethylsilyl group, a tri-n-propylsilyl group, a tri-isopropylsilyl group, a tris(trimethylsilyloxy)silyl group, a methylbis(trimethylsilyloxy)silyl group, and a dimethyl(trimethylsilyloxy)silyl group.
• the monovalent cyclic polysiloxane residue is preferably a group represented by formula (T1).
• R 3 's each independently represent a hydrocarbon group, a hydrocarbon group having a substituent, or a group represented by -O-SiR 51 3 ; s is an integer from 1 to 4; Each R 51 independently represents a hydrocarbon group or a trialkylsilyloxy group; * indicates the bond position.
• hydrocarbon group represented by R3 examples include an aliphatic hydrocarbon group and an aromatic hydrocarbon group.
• the hydrocarbon group is preferably an aliphatic hydrocarbon group, and more preferably an alkyl group.
• the alkyl group as one embodiment of the hydrocarbon group represented by R3 may be any of a linear alkyl group, a branched alkyl group, and a cyclic alkyl group, but a linear alkyl group is preferred.
• the number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 8, and even more preferably 1 to 4.
• the alkyl group represented by R3 is preferably a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an isobutyl group, or a heptyl group, and more preferably a methyl group.
• Examples of the hydrocarbon group contained in the hydrocarbon group having a substituent represented by R3 include an aliphatic hydrocarbon group and an aromatic hydrocarbon group.
• the hydrocarbon group is preferably an aliphatic hydrocarbon group, and more preferably an alkyl group.
• the alkyl group may be any of a linear alkyl group, a branched alkyl group, and a cyclic alkyl group, but a linear alkyl group is preferred.
• the number of carbon atoms in the alkyl group contained in the substituted alkyl group is preferably 1 to 10, more preferably 1 to 8, and even more preferably 2 to 4.
• Examples of the substituent in the substituted hydrocarbon group represented by R 3 include a halogen atom, a hydroxyl group, an alkoxy group, a trialkylsilyl ether group, a trialkylsilyl group, an amino group, a nitro group, a cyano group, a sulfonyl group, a trifluoromethyl group, and a group represented by -SiR 52 3.
• Each R 52 is independently a hydrocarbon group or a trialkylsilyloxy group.
• Examples of the hydrocarbon group represented by R52 include the same as the hydrocarbon group represented by R3 .
• the alkyl group contained in the trialkylsilyloxy group represented by R52 may be any of a linear alkyl group, a branched alkyl group, and a cyclic alkyl group, but a linear alkyl group is preferred.
• the number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 8, still more preferably 1 to 4, and particularly preferably 1.
• the three alkyl groups contained in the trialkylsilyloxy group may be the same or different from each other.
• the three R 52 may be the same or different from each other, but from the viewpoint of ease of production, it is preferable that they are the same.
• each R 51 is independently a hydrocarbon group or a trialkylsilyloxy group.
• the hydrocarbon group represented by R 51 include the same as the hydrocarbon group represented by R 3.
• the trialkylsilyloxy group represented by R 51 include the same as the trialkylsilyloxy group represented by R 52 .
• the multiple R3s may be the same or different from one another, but from the viewpoint of ease of production, they are preferably the same.
• Examples of monovalent cyclic polysiloxane residues include the following groups. * indicates the bond position.
• the monovalent cage polysiloxane residue is preferably a group represented by formula (T2).
• Each R4 is independently a hydrocarbon group or a trialkylsilyloxy group; * indicates the bond position.
• Examples of the hydrocarbon group represented by R4 include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. Among them, the hydrocarbon group is preferably an aliphatic hydrocarbon group, and more preferably an alkyl group.
• the alkyl group may be any of a linear alkyl group, a branched alkyl group, and a cyclic alkyl group, and is preferably a linear alkyl group or a branched alkyl group.
• the number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4.
• the hydrocarbon group represented by R4 is more preferably a methyl group, an ethyl group, an n-propyl group, an n-butyl group, or an isobutyl group, and is particularly preferably an isobutyl group.
• the alkyl group contained in the trialkylsilyloxy group represented by R4 may be any one of a linear alkyl group, a branched alkyl group, and a cyclic alkyl group, but a linear alkyl group is preferred.
• the number of carbon atoms in the alkyl group contained in the trialkylsilyloxy group represented by R4 is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4.
• the hydrocarbon group represented by R1 is more preferably a methyl group, an ethyl group, an n-propyl group, or an n-butyl group, and even more preferably a methyl group.
• a plurality of R 4s may be the same or different from each other, and from the viewpoint of ease of production, they are preferably the same.
• each R 2 is independently a hydrocarbon group or a trialkylsilyloxy group. It is preferable that each R 2 is independently a hydrocarbon group.
• R2 preferably has 1 to 10 carbon atoms, more preferably has 1 to 6 carbon atoms, and further preferably has 1 to 4 carbon atoms.
• R2 is a hydrocarbon group
• the hydrocarbon group is preferably an aliphatic hydrocarbon group, more preferably an alkyl group.
• the alkyl group may be any of a linear alkyl group, a branched alkyl group, and a cyclic alkyl group, but a linear alkyl group is preferred.
• the number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4.
• a methyl group, an ethyl group, an n-propyl group, or an n-butyl group is more preferred, and a methyl group is particularly preferred.
• the alkyl group contained in the trialkylsilyloxy group may be any one of a linear alkyl group, a branched alkyl group, and a cyclic alkyl group, but a linear alkyl group is preferred.
• the number of carbon atoms in the alkyl group contained in the trialkylsilyloxy group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4.
• the alkyl group contained in the trialkylsilyloxy group is more preferably a methyl group, an ethyl group, an n-propyl group, or an n-butyl group, and even more preferably a methyl group.
• each R is independently a hydrocarbon group.
• Examples of the hydrocarbon group represented by R include the hydrocarbon group represented by R2 .
• each L is independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group.
• a hydrolyzable group is a group that becomes a hydroxyl group through a hydrolysis reaction. That is, a hydrolyzable silyl group represented by Si-L becomes a silanol group represented by Si-OH through a hydrolysis reaction.
• the silanol groups further react with each other to form Si-O-Si bonds.
• the silanol groups can undergo a dehydration condensation reaction with silanol groups derived from oxides present on the surface of the substrate to form Si-O-Si bonds.
• hydrolyzable groups examples include alkoxy groups, aryloxy groups, halogen atoms, acyl groups, acyloxy groups, and isocyanato groups (-NCO).
• the alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms.
• the aryloxy group is preferably an aryloxy group having 3 to 10 carbon atoms.
• the 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.
• Examples of the group having a hydrolyzable group include the groups having a hydrolyzable group exemplified above.
• the group having a hydrolyzable group is preferably -OL A -L B.
• L A is an alkylene group
• L B is a hydrolyzable group.
• the number of carbon atoms in the alkylene group is preferably 1 to 10.
• the hydrolyzable group represented by L B has the same meaning as the hydrolyzable group represented by L described above, and the preferred embodiments are also the same.
• L is preferably an alkoxy group having 1 to 4 carbon atoms or a halogen atom.
• L is preferably an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group or a methoxy group, from the viewpoint of less outgassing during application and better storage stability of the compound.
• m is a number of 0 or more. m may be 1 or more. m is preferably a number from 2 to 600, more preferably a number from 3 to 500, further preferably a number from 9 to 50, particularly preferably a number from 11 to 30, and most preferably a number from 11 to 25.
• the number m of repeating units represented by "(Si(R 2 ) 2 -O)" is an average value calculated from data obtained by measuring the compound by nuclear magnetic resonance (NMR) spectroscopy.
• each n is independently an integer of 0 to 2.
• n is preferably 0 or 1, and more preferably 0.
• the adhesion of the surface treatment layer to the substrate is strengthened.
• the multiple Ls present in one molecule may be the same or different from each other. From the viewpoint of availability of raw materials and ease of manufacturing the compound, it is preferable that the multiple Ls are the same.
• the multiple Rs present in one molecule may be the same or different from each other. From the viewpoint of availability of raw materials and ease of manufacturing the compound, it is preferable that the multiple Rs are the same.
• q is an integer of 1 or more.
• q is preferably an integer of 1 to 15, more preferably an integer of 1 to 6, further preferably an integer of 1 to 4, and particularly preferably an integer of 1 to 3.
• the multiple [Si(R) n L 3-n ] may be the same or different from each other. From the viewpoint of availability of raw materials and ease of production of the compound, it is preferable that the multiple [Si(R) n L 3-n ] are the same.
• A is a (q+1)-valent linking group having an alicyclic structure which may have a heteroatom.
• a ring constituting an alicyclic structure which may have a heteroatom contained in the compound of the present disclosure is also referred to as a "specific ring structure”.
• the specific ring structure of A may be any of a monocycle, a condensed polycycle, a bridged ring, a spiro ring, and an aggregate polycycle, so long as it is a ring that does not have aromaticity, and the atoms constituting the ring may be a carbocycle consisting of only carbon atoms, or a heterocycle consisting of a heteroatom having a valence of 2 or more and a carbon atom.
• the bond between the atoms constituting the ring may be a single bond, or may be a multiple bond as long as the ring is non-aromatic.
• the bridged ring As the bridged ring, a bridged ring having a maximum ring size of 5 or 6 is preferred, and an adamantane ring is more preferred.
• the spiro ring is preferably a spiro ring consisting of two 4- to 6-membered rings.
• the assembled polycyclic ring is preferably an assembled polycyclic ring in which two or three rings selected from five-membered rings and six-membered rings are bonded via single bonds.
• the heteroatom constituting the specific ring structure is preferably a nitrogen atom, an oxygen atom, a sulfur atom or a silicon atom, more preferably a nitrogen atom or an oxygen atom.
• the number of heteroatoms constituting the specific ring structure is preferably 3 or less. In addition, when the number of heteroatoms constituting the specific ring structure is 2 or more, these heteroatoms may be the same or different.
• the specific ring structure from the viewpoints of ease of production of the compound and further superior light resistance of the surface treatment layer, it is preferable to use one selected from the group consisting of a 3- to 8-membered aliphatic ring, a 3- to 8-membered heteroaliphatic ring, a fused ring in which 2 to 4 of these rings are fused, a bridged ring in which the maximum ring is a 5- or 6-membered ring, and an assembled polycyclic ring having two or more of these rings and linked by a single bond.
• Preferred rings are 5- or 6-membered aliphatic rings, 5- or 6-membered heterocycles having a nitrogen atom or an oxygen atom, fused rings in which 2 to 4 5- or 6-membered carbocycles are fused, bridged rings in which the maximum ring is a 5- or 6-membered ring, or fused rings of a bridged ring in which the maximum ring is a 5- or 6-membered ring and a 5-membered heterocycle.
• Examples of the specific ring structure include the rings shown below, as well as a 1,3-cyclohexadiene ring, a 1,4-cyclohexadiene ring, a cyclopropane ring, a norbornene ring, a norbornadiene ring, a morpholine ring, an aziridine ring, a pyran ring, and an indene ring.
• R is a hydrogen atom or a methyl group.
• A may be composed only of the specific ring structure, or may be a group consisting of at least one specific ring structure and at least one divalent or higher linking group in combination.
• the divalent or higher linking group that A may have may be any group that does not impair the effects of the present disclosure, and examples thereof include an alkylene group that may have an etheric oxygen atom or a divalent organopolysiloxane residue, a carbon atom, a nitrogen atom, a silicon atom, and a divalent to octavalent organopolysiloxane residue, as well as [-L 1 -L 2 -L 3 -] in formula (2), [-L 4 -L 5 -(L 6 -*) r ] in formula (3), and [-L 7 -L 8 -L 9 -L 10 -(L 11 -*) s ] in formula (4) described below.
• * represents the bonding position with [Si(R) n L 3-n ].
• the compound represented by formula (1-1) is preferably a compound represented by the following formula (2), a compound represented by the following formula (3), or a compound represented by the following formula (4).
• L 1 is
• L4 is a single bond or a divalent linking group
• L5 is a (r+1)-valent alicyclic group which may have a heteroatom
• L6 is each independently a single bond or a divalent linking group
• r is an integer of 1 or more.
• L7 and L9 each independently represent a single bond or a divalent linking group
• L8 represents a divalent alicyclic group which may have a heteroatom
• L10 represents a (r+1)-valent alicyclic group which may have a heteroatom
• L11 each independently represent a single bond or a divalent linking group
• s represents an integer of 1 or greater.
• the compound represented by formula (2) or the compound represented by formula (4) is more preferred.
• the compound represented by formula (1-1) may be a compound represented by formula (2) above.
• L 1 is a single bond or a divalent linking group.
• the divalent linking group include divalent hydrocarbon groups, -O-, -S-, -SO 2 -, -N(R d )-, -C(O)-, -Si(R a ) 2 -, and groups formed by combining two or more of these.
• the end of L 1 on the —Si(R 2 ) 2 — side is not —O—Si(R a ) 2 —.
• the divalent linking group for L1 is preferably a divalent group other than a divalent alicyclic group which may have a heteroatom.
• the divalent hydrocarbon group may be a divalent linear or branched saturated hydrocarbon group, an alkenylene group, or an alkynylene group.
• Examples of the divalent linear or branched saturated hydrocarbon group include an alkylene group.
• the number of carbon atoms in the alkylene group is preferably 1 to 30, more preferably 1 to 20, further preferably 4 to 20, and particularly preferably 5 to 15.
• the number of carbon atoms in the alkenylene group is preferably 2 to 20, and the number of carbon atoms in the alkynylene group is preferably 2 to 20.
• the above R a is an alkyl group (preferably having 1 to 10 carbon atoms)
• 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 these include, -C(O)O-, -C(O)S-, -C(O)N(R d )-, -N(R d )C(O)N(R d )-, -N(R d )C(O)O-, -SO 2 N(R d )-, an alkylene group having -C(O) N(R d )-, an alkylene group having -OC(O)N(R d ) - , an alkylene group having an etheric oxygen atom, an alkylene group having -S-, an alkylene group having -C(O)O-, an alkylene group having -C(O)S-, an alkylene group having -N(R d )-, an alkylene group having -N(R d )C(O)N(R d )-, -SO 2 N(R d ) -
• L 1 is a single bond, a divalent alkylene group, -O-, -S-, -SO 2 -, -N(R d )-, -C(O)-, -Si(R a ) 2 -, -C(O)O-, -C(O)S-, -C(O)N(R d )-, -N(R d )C(O)N(R d )-, -N(R d )C(O)O-, -SO 2 N(R d )-, an alkylene group having -C(O)N(R d )-, an alkylene group having -OC(O)N(R d )-, an alkylene group having an etheric oxygen atom, an alkylene group having -S-, an alkylene group having -C(O)O-, an alkylene group having -C(O)S-, -N
• L2 is a divalent alicyclic group which may have a heteroatom.
• the divalent alicyclic group which may have a heteroatom is a group having the specific ring structure described above, and the preferred embodiments are also the same.
• L2 preferably contains a ring selected from the group consisting of a cyclopentane ring, a cyclohexane ring, an adamantane ring, a piperidine ring, and the following fused rings, and more preferably contains an adamantane ring.
• the definition of R is as described above.
• a bond that does not constitute a ring of an atom that constitutes a specific ring structure is a bond that is bonded to L1 or L3 .
• the remaining bond is bonded to a hydrogen atom or a substituent.
• the remaining bond is preferably bonded to a hydrogen atom or an alkyl group, and more preferably bonded to a hydrogen atom.
• the number of carbon atoms in the alkyl group is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1.
• L3 is a (q+1)-valent linking group.
• L3 is preferably the group (3-1A) or the group (3-1B), more preferably the group (3-1A).
• Q a represents a single bond or a divalent linking group.
• X 31 is an alkylene group
• the end of Q a bonding to X 31 is not an alkylene group.
• the divalent linking group is the same as that explained above for L1 .
• Q a is a divalent alkylene group, —O—, —S—, —SO 2 —, —N(R d )—, —C(O)—, —Si(R a ) 2 —, —C(O)O—, —C(O)S—, —C(O)N(R d )—, —N(R d )C(O)N(R d )—, —N(R d )C(O)O—, —SO 2 N(R d )—, an alkylene group having —C(O)N(R d ) —, an alkylene group having —OC(O)N(R d )—, an alkylene group having an etheric oxygen atom, an alkylene group having —S—, an alkylene group having —C(O)O—, an alkylene group having —C(O)S—, an alkylene group having an ether
• X 31 represents an alkylene group, a nitrogen atom, a carbon atom, a silicon atom, or a divalent to octavalent organopolysiloxane residue.
• the alkylene group may have -O-, 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 divalent organopolysiloxane residue, and a dialkylsilylene group.
• the alkylene group represented by X 31 preferably has 1 to 20 carbon atoms, and more preferably has 1 to 10 carbon atoms.
• Examples of the divalent to octavalent organopolysiloxane residue include a divalent organopolysiloxane residue and a (w+1)-valent organopolysiloxane residue described below.
• X 31 is preferably a nitrogen atom, a carbon atom, a silicon atom, or a tetravalent to octavalent organopolysiloxane residue, and more preferably a carbon atom.
• Q b is a single bond or a divalent linking group.
• the divalent linking group is the same as that explained above in relation to Qa .
• the two or more Q b's may be the same or different.
• Q b is preferably an alkylene group which may have an etheric oxygen atom.
• the number of carbon atoms in the alkylene group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 2 to 20, and may be 2 to 10, 2 to 6, or 2 to 5. Examples include 2, 3, 8, 9, and 11. The number of carbon atoms may be 1 to 10.
• R 31 is a hydrogen atom, a hydroxyl group or an alkyl group.
• the two or more (-R 31 s ) may be the same or different.
• the alkyl group preferably has 1 to 5 carbon atoms, more preferably 1 to 3 carbon atoms, and even more preferably 1 carbon atom.
• i is preferably 0 or 1 from the viewpoint of improving the light resistance of the surface treatment layer.
• h is preferably 2 or 3.
• Q c is a single bond or a divalent linking group.
• the divalent linking group is the same as that explained above for L1 .
• R 32 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and is preferably a hydrogen atom in terms of ease of production of the compound.
• the alkyl group is preferably a methyl group.
• Qd is a single bond or an alkylene group.
• the alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and may have 1 to 10 carbon atoms or 1 to 6 carbon atoms. In addition, the alkylene group may have 2 to 20 carbon atoms.
• R 33 is a hydrogen atom or a halogen atom, and is preferably a hydrogen atom in terms of ease of production of the compound.
• y is an integer of 1 to 10, and preferably an integer of 1 to 6.
• Two or more [CH 2 C(R 32 )(-Q d -*)] may be the same or different.
• the groups (3-1A-1) to (3-1A-7) are preferred.
• the group (3-1A) is preferably a group obtained by removing Si(R) n L 3-n from the group (3-1A-1) or the group (3-1A-4), and more preferably a group obtained by removing Si(R) n L 3-n from the group (3-1A-4).
• L a represents a single bond or an alkylene group.
• the alkylene group has the same meaning as the alkylene group exemplified as the divalent linking group represented by L1 , and preferred embodiments are also the same.
• X 32 is —O—, —S—, —N(R d )—, —C(O)—, —C(O)O—, —C(O)S—, —SO 2 N(R d )—, —N(R d )C(O)N(R d )—, —OC(O)N(R d )—, or —C(O)N( R d ) — (wherein N in the formula is bonded to Q b1 ).
• Rd is 0 or 1.
• X 32 is preferably —O—, —S—, —N(R d )—, —C(O)O—, —C(O)S—, —N(R d )C(O)N(R d )—, —OC(O)N(R d )— or —C(O)N(R d ) —, and more preferably —C(O)O— or —C(O)N(R d )—.
• Q b1 is a single bond or an alkylene group.
• the alkylene group may have -O- or a dialkylsilylene group.
• the alkylene group may have a plurality of groups selected from the group consisting of -O-, a divalent organopolysiloxane residue, and a dialkylsilylene group.
• the alkylene group has --O--, a divalent organopolysiloxane residue or a dialkylsilylene group, it is preferable that such a group be present between carbon atoms.
• the alkylene group represented by Q b1 has preferably 1 to 30 carbon atoms, more preferably 1 to 20, further preferably 2 to 20, and particularly preferably 2 to 6. The number of carbon atoms may be 1 to 10.
• s1 is preferably 1, and Q b1 is preferably an alkylene group having 2 to 6 carbon atoms.
• Examples of [-(X 32 ) s1 -Q b1 -Si(R) n L 3-n ] in the group (3-1A-1) include the following groups: In the following formula, * indicates the bonding position with L 2 .
• X33 is -O-, -S-, -N(R d )-, -C(O)-, -C(O)O-, -C(O)S-, -SO 2 N(R d )-, -N(R d )C(O)N(R d )-, -OC(O)N(R d )-, or -C(O)N( R d ) -.
• Rd The definition and preferred embodiments of Rd are as described above.
• s2 is 0 or 1.
• s2 is preferably 0 from the viewpoint of ease of production of the compound.
• Q a2 is a single bond, an alkylene group, -C(O)-, or an alkylene group having 2 or more carbon atoms having an ether oxygen atom between carbon atoms, -C(O)-, -C(O)O-, -N(R d )C(O)N(R d )-, -N(R d )C(O)O-, -SO 2 N(R d )-, -C(O)N(R d )-, or -NH-.
• Rd The definition and preferred embodiments of Rd are as described above.
• the alkylene group represented by Q a2 preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, further preferably 1 to 6 carbon atoms, and particularly preferably 1 to 3 carbon atoms.
• the number of carbon atoms in the group having an ether oxygen atom, -C(O)-, -C(O)O-, -N(R d )C(O)N(R d )-, -N(R d )C(O)O-, -SO 2 N(R d ) -, -C(O)N(R d )- or -NH- between carbon atoms in the alkylene group having 2 or more carbon atoms represented by Q a2 is preferably 2 to 10, and more preferably 2 to 6.
• Q a2 is preferably a single bond from the viewpoint of ease of production of the compound.
• Q b2 is an alkylene group or an alkylene group having 2 or more carbon atoms which has a divalent organopolysiloxane residue, an ether oxygen atom, or an --NH-- group between carbon atoms.
• the alkylene group represented by Q b2 has preferably 1 to 30 carbon atoms, more preferably 1 to 20, and still more preferably 2 to 20, and may have 2 to 10 or may have 2 to 6 carbon atoms. Examples include 2, 3, 8, 9, and 11. The number of carbon atoms may also be 1 to 10.
• the alkylene group having 2 or more carbon atoms represented by Q b2 preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms, in the divalent organopolysiloxane residue, the group having an ether oxygen atom, or the group having -NH- between carbon atoms.
• --CH 2 CH 2 CH 2 -- and --CH 2 CH 2 OCH 2 CH 2 CH 2 -- are preferred (wherein the right side bonds to Si).
• the two [-Q b2 -Si(R) n L 3-n ] may be the same or different.
• Examples of [-(X 33 ) s2 -Q a2 -N[-Q b2 -Si(R) n L 3-n ] 2 ] in the group (3-1A-2) include the following groups:
• * indicates the bonding position with L 2 .
• ⁇ in (CH 2 ) ⁇ bonded to the reactive silyl group is an integer representing the number of methylene groups, and 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. The number of carbon atoms may be 1 to 10.
• Multiple ⁇ contained in the same compound may be the same or different, but are preferably the same. For example, multiple ⁇ contained in the same compound are all 2, 3, 8, 9, and 11. The same applies below.
• Q a3 is a single bond or an alkylene group which may have an etheric oxygen atom. From the viewpoint of ease of production of the compound, Q a3 is preferably a single bond.
• the alkylene group which may have an etheric oxygen atom preferably has 1 to 10 carbon atoms, and more preferably has 2 to 6 carbon atoms.
• Rg is a hydrogen atom, a hydroxyl group or an alkyl group. From the viewpoint of ease of production of the compound, Rg is preferably a hydrogen atom or an alkyl group.
• the alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 4 carbon atoms, and further preferably is a methyl group.
• Q b3 is an alkylene group or a group having an ether oxygen atom or a divalent organopolysiloxane 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, and still more preferably 2 to 20, and may be 2 to 10 or may be 2 to 6. Examples include 2, 3, 8, 9, and 11. The number of carbon atoms may be 1 to 10.
• the alkylene group having 2 or more carbon atoms, represented by Q b3 , and having an ether oxygen atom or a divalent organopolysiloxane residue between carbon atoms preferably has 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms, and even more preferably 2 to 6 carbon atoms.
• Q b3 is preferably -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, or -CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 - from the viewpoint of ease of production of the compound.
• the two [-Q b3 -Si(R) n L 3-n ] may be the same or different.
• Examples of the group (3-1A-3) include the following groups: In the following formula, * indicates the bonding position with L2 .
• Q e is —C(O)O—, —SO 2 N(R d )—, or —C(O)N(R d )—.
• R 31 is preferably a hydrogen atom.
• s4 is 0 or 1.
• Q a4 is a single bond or an alkylene group which may have an etheric oxygen atom.
• the alkylene group which may have an etheric oxygen atom preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, further preferably 1 to 6 carbon atoms, and particularly preferably 1 to 3 carbon atoms.
• t4 is 0 or 1, provided that when Q a4 is a single bond, it is 0.
• -Q a4 -(O) t4 - from the viewpoint of ease of production of the compound, when s4 is 0, a single bond, -CH 2 O- , -CH 2 OCH 2 -, -CH 2 OCH 2 CH 2 OCH 2 -, -CH 2 OCH 2 CH 2 OCH 2 - or -CH 2 OCH 2 CH 2 CH 2 CH 2 OCH 2 - is preferred (with the left side bonding to L 2 ), and when s4 is 1, a single bond, -CH 2 - or -CH 2 CH 2 - is preferred.
• Q b4 is an alkylene group, and the alkylene group may have -O-, -C(O)N(R d )- (R d is as defined above), a divalent organopolysiloxane residue, or a dialkylsilylene group.
• R d is as defined above
• the alkylene group has -O-, it is preferable that it has -O- between carbon atoms.
• the alkylene group has -C(O)N(R d )-, a dialkylsilylene group, or a divalent organopolysiloxane residue, it is preferable that it has such a group between carbon atoms or at the end of the side bonding to (O) u4 .
• the number of carbon atoms in the alkylene group represented by Q b4 is preferably 1 to 30, more preferably 1 to 20, and still more preferably 2 to 20, and may be 2 to 11 or may be 2 to 6. Examples include 2, 3, 8, 9, and 11. The number of carbon atoms may be 1 to 11.
• u4 is 0 or 1.
• -(O) u4 -Q b4 -, -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -(CH 2 ) b -, -CH 2 OCH 2 CH 2 CH 2 -, -CH 2 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 -, -CH 2 CH 2 CH 2 Si(CH 3 ) 2 PhSi(CH 3 ) 2 CH 2 CH 2 - are preferred from the viewpoint of ease of production of the compound (wherein the right side is bonded to Si).
• b is an integer from 4 to 11.
• w1 is an integer of 0 to 2, preferably 0 or 1, and more preferably 0.
• the two or more [-(O) u4 - Qb4 -Si(R) nL3 -n ] may be the same or different.
• the two or more (-R 31 s ) may be the same or different.
• Examples of [-[Q e ] s4 -Q a4 -(O) t4 -C[-(O) u4 -Q b4 -Si(R) n L 3-n ] 3-w1 (-R 31 ) w1 ] in the group (3-1A-4) include the following groups. In the following formula, * indicates the bonding position with L 2 .
• Q a5 is an alkylene group which may have an etheric oxygen atom.
• the alkylene group which may have an etheric oxygen atom preferably has 1 to 10 carbon atoms, and more preferably has 2 to 6 carbon atoms.
• Q a5 is preferably -OCH 2 CH 2 CH 2 -, -OCH 2 CH 2 OCH 2 CH 2 CH 2 -, -CH 2 CH 2 - or -CH 2 CH 2 CH 2 - (wherein the right side is bonded to Si) in terms of ease of production of the compound.
• Q b5 is an alkylene group or an alkylene group having 2 or more carbon atoms which has an ether oxygen atom or a divalent organopolysiloxane residue between carbon atoms.
• the number of carbon atoms in the alkylene group represented by Q b5 is preferably 1 to 30, more preferably 1 to 20, and still more preferably 2 to 20, and may be 2 to 10 or may be 2 to 6. Examples include 2, 3, 8, 9, and 11. The number of carbon atoms may be 1 to 10.
• the alkylene group having 2 or more carbon atoms, represented by Q b5 , and having an ether oxygen atom or a divalent organopolysiloxane residue between carbon atoms preferably has 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms, and even more preferably 2 to 6 carbon atoms.
• Q b5 is preferably --CH 2 CH 2 CH 2 -- or --CH 2 CH 2 OCH 2 CH 2 CH 2 -- (wherein the right side bonds to Si(R) n L 3-n ) in terms of ease of production of the compound.
• the three [-Q b5 -Si(R) n L 3-n ] may be the same or different.
• Examples of the group (3-1A-5) include the following groups: In the following formula, * indicates the bonding position with L2 .
• Q a6 is an alkylene group which may have an etheric oxygen atom.
• the alkylene group which may have an etheric oxygen atom preferably has 1 to 10 carbon atoms, and more preferably has 2 to 6 carbon atoms.
• Q a6 is preferably —CH 2 OCH 2 CH 2 CH 2 —, —CH 2 OCH 2 CH 2 OCH 2 CH 2 CH 2 —, —CH 2 CH 2 — or —CH 2 CH 2 CH 2 — from the viewpoint of ease of production of the compound (wherein the right side bonds to Z a ).
• Z a is a (w2+1)-valent organopolysiloxane 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 the (w2+1)-valent organopolysiloxane residue and the (w2+1)-valent group having an alkylene group between the organopolysiloxane residues include the following groups, where R a in the following formula is as defined above. * indicates a bonding position.
• Q b6 is an alkylene group or a group having an ether oxygen atom or a divalent organopolysiloxane residue between carbon atoms in an alkylene group having 2 or more carbon atoms.
• the number of carbon atoms in the alkylene group represented by Q b6 is preferably 1 to 30, more preferably 1 to 20, and still more preferably 2 to 20, and may be 2 to 10 or may be 2 to 6. Examples include 2, 3, 8, 9, and 11. The number of carbon atoms may be 1 to 10.
• the alkylene group having 2 or more carbon atoms, represented by Q b6 which has an ether oxygen atom or a divalent organopolysiloxane residue between carbon atoms, preferably has 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms, and even more preferably 2 to 6 carbon atoms.
• Q b6 is preferably —CH 2 CH 2 — or —CH 2 CH 2 CH 2 — from the viewpoint of ease of production of the compound.
• the w2 groups of [-Q b6 -Si(R) n L 3-n ] may be the same or different.
• Examples of [-[Q e ] v -Q a6 -Z a [-Q b6 -Si(R) n L 3-n ] w2 ] in the group (3-1A-6) include the following groups: In the following formula, * indicates the bonding position with L 2 .
• Zc is a (w3+w4+1)-valent hydrocarbon group.
• w3 is an integer of 4 or greater.
• w4 is an integer of 0 or greater.
• the definitions and preferred ranges of Q e , s4, Q a4 , t4, Q b4 and u4 are the same as those of each symbol in the group (3-1A-4).
• Zc may be composed of a hydrocarbon chain, and may have an ether oxygen atom between carbon atoms of the hydrocarbon chain, and is preferably composed of a hydrocarbon chain.
• the valence of Zc is preferably from 5 to 20, more preferably from 5 to 10, further preferably from 5 to 8, and particularly preferably from 5 to 6.
• Zc preferably has 3 to 50 carbon atoms, more preferably has 4 to 40 carbon atoms, and further preferably has 5 to 30 carbon atoms.
• w3 is preferably 4 to 20, more preferably 4 to 16, further preferably 4 to 8, and particularly preferably 4 or 5.
• w4 is preferably an integer of 0 to 10, more preferably an integer of 0 to 8, still more preferably an integer of 0 to 6, particularly preferably an integer of 0 to 3, and most preferably an integer of 0 to 1.
• the two or more [-(OQ b4 ) u4 -Si(R) n L 3-n ] may be the same or different.
• Examples of [-[Q e ] s4 -Q a4 -(O) t4 -Z c [-(O-Q b4 ) u4 -Si(R) n L 3-n ] w3 (-OH) w4 ] in the group (3-1A-7) include the following groups. In the following formula, * indicates the bonding position with L 2 .
• L a is bonded to L 2 , and Q 22 , Q 23 , Q 25 or Q 26 is bonded to [—Si(R) n L 3-n ].
• the definition and preferred embodiments of L a are as described above.
• a 1 is a single bond, —C(O)NR 6 —, —C(O)—, —OC(O)O—, —NHC(O)O—, —NHC(O)NR 6 —, —O— or —SO 2 NR 6 —.
• Q 11 is a single bond, —O—, an alkylene group, or an alkylene group having 2 or more carbon atoms which has —C(O)NR 6 —, —C(O)—, —NR 6 — or O— between carbon atoms.
• Q 12 is a single bond, an alkylene group, or an alkylene group having 2 or more carbon atoms which has --C(O)NR 6 --, --C(O)--, --NR 6 -- or --O-- between carbon atoms.
• Q13 is a single bond (with the proviso that A1 is -C(O)-), an alkylene group, an alkylene group having 2 or more carbon atoms having -C(O) NR6- , -C(O)-, -NR6- or -O- between carbon atoms, or an alkylene group having -C(O)- at the N-terminal.
• Q 15 is an alkylene group or an alkylene group having 2 or more carbon atoms which has --C(O)NR 6 --, --C(O)--, --NR 6 -- or --O-- between carbon atoms.
• Q 22 is an alkylene group, a group having -C(O)NR 6 -, -C(O)-, -NR 6 - or -O- between carbon-carbon atoms of an alkylene group having 2 or more carbon atoms, a group having -C(O)NR 6 -, -C(O)-, -NR 6 - or -O- at the end of the alkylene group not connected to Si, or a group having -C(O)NR 6 -, -C(O)-, -NR 6 - or -O- between carbon-carbon atoms of an alkylene group having 2 or more carbon atoms and having -C(O)NR 6 -, -C(O)-, -NR 6 - or -O- at the end of the side not connected to Si, and when there are two or more Q 22 , the two or more Q 22 may be the same or different.
• Q 23 is an alkylene group or a group having --C(O)NR 6 --, --C(O)--, --NR 6 -- or O-- between carbon atoms of an alkylene group having 2 or more carbon atoms, and two Q 23 's may be the same or different.
• Q25 is an alkylene group or a group having -C(O) NR6- , -C(O)-, -NR6- or -O- between carbon atoms in an alkylene group having 2 or more carbon atoms, and when there are two or more Q25s , the two or more Q25s may be the same or different.
• Q 26 is an alkylene group or an alkylene group having 2 or more carbon atoms which has --C(O)NR 6 --, --C(O)--, --NR 6 -- or --O-- between carbon atoms.
• Q 22 , Q 23 , Q 25 and Q 26 are each an alkylene group, they preferably have 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, and even more preferably 1 to 6 carbon atoms.
• R e1 is a hydrogen atom or an alkyl group, and two or more R e1's may be the same or different.
• R e2 is a hydrogen atom, a hydroxyl group, an alkyl group or an acyloxy group.
• R e3 is an alkyl group.
• R6 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.
• d1 is 0 or 1.
• d3 is 0 or 1.
• d1+d3 is 1.
• d2 is an integer of 0 to 3.
• d4 is an integer of 0 to 3.
• d2+d4 is an integer of 1 to 5.
• d1+d2 is an integer from 1 to 3.
• d3+d4 is an integer from 1 to 3.
• e2 is an integer of 1 to 3, and is preferably 2 or 3.
• i2 is an integer of 1 to 3, and is preferably 2 or 3.
• i3 is 2 or 3.
• the number of carbon atoms in the alkylene group of Q 12 , Q 13 , Q 15 , Q 22 , Q 23 , Q 25 and Q 26 is preferably 1 to 30, more preferably 1 to 20, and even more preferably 2 to 20, from the viewpoints of ease of production of the compound and further superior light resistance of the surface treatment layer, and may be 2 to 10 or 2 to 6. Examples include 2, 3, 8, 9 and 11.
• the number of carbon atoms may be 1 to 10, 1 to 6 or 1 to 4. However, the lower limit of the number of carbon atoms in the alkylene group in the case where a specific bond is present between a carbon-carbon atom is 2.
• the number of carbon atoms in the alkyl group of R e2 or R e3 is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 or 2, from the viewpoint of ease of production of the compound.
• the number of carbon atoms in the alkyl group portion of the acyloxy group for R e2 is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 or 2, from the viewpoint of ease of production of the compound.
• G 1 is the following group (g3), and two or more G 1s in A may be the same or different.
• the symbols other than G 1 are the same as the symbols in formulae (g2-1) to (g2-3) and (g2-5) to (g2-7).
• -Si(R 8 ) 3-k3 (-Q 3 -) k3 ...(g3)
• the Si side is connected to Q 22 , Q 23 , Q 25 or Q 26
• 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 the carbon-carbon atoms of an alkylene group having 2 or more carbon atoms, or (OSi(R 9 ) 2 ) p -O-, and two or more Q 3s may be the same or different.
• k3 is 2 or 3.
• R 6 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a phenyl group.
• R 9 is an alkyl group, a phenyl group or an alkoxy group, and two R 9s may be the same or different.
• p is an integer of 0 to 5, and when p is 2 or more, the two or more (OSi(R 9 ) 2 ) may be the same or different.
• the number of carbon atoms in the alkylene group of Q3 is preferably 1 to 30, more preferably 1 to 20, and still more preferably 2 to 20, from the viewpoints of ease of production of the compound and further superior light resistance of the surface treatment layer, and may be 2 to 10 or 2 to 6. Examples include 2, 3, 8, 9, and 11.
• the number of carbon atoms may be 1 to 10, 1 to 6, or 1 to 4.
• the lower limit of the number of carbon atoms in the alkylene group in the case where a specific bond is present between a carbon-carbon atom is 2.
• the number of carbon atoms in the alkyl group of R 8 is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 or 2, from the viewpoint of ease of production of the compound.
• the number of carbon atoms in the alkyl group of R 9 is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 or 2, from the viewpoint of ease of production of the compound.
• the number of carbon atoms in the alkoxy group of R 9 is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 or 2, in terms of excellent storage stability of the compound.
• p is preferably 0 or 1.
• Compound (2) may be a compound in which L 1 is an alkylene group, L 2 is a specific ring structure, and L 3 is an alkylene group.
• the alkylene groups in L 1 and L 3 may be linear or branched, but linear is preferred.
• the number of carbon atoms in the alkylene groups in L 1 and L 3 is preferably 1 to 30, and may be 1 to 25, 1 to 20, 1 to 10, or 5 to 10.
• L 1 and L 3 may be alkylene groups having 1 to 10 or 5 to 10 carbon atoms
• L 2 may be a combination of a specific ring structure.
• q may be 1.
• the compound represented by formula (1-1) may be a compound represented by formula (3).
• R 1 , R 2 , m, R, L and n in formula (3) are the same as those of R 1 , R 2 , m, R, L and n in formula (2), and the preferred embodiments are also the same.
• L4 is a single bond or a divalent linking group.
• the divalent linking group represented by L4 has the same meaning as the divalent linking group represented by L1 in the above formula (2), and preferred embodiments are also the same.
• L 4 is a divalent alkylene group, -O-, -S-, -SO 2 -, -N(R d )-, -C(O)-, -Si(R a ) 2 -, -OC(O)-, -C(O)O-, -C(O)S-, -C(O)N(R d )-, -N(R d )C(O)-, -N(R d )C(O)N(R d )-, -N(R d )C(O)O-, -OC(O)N(R d )-, -SO 2 N(R d )-, -N(R d )SO 2 -, an alkylene group having -C(O)-, an alkylene group having -C(O)N(R d )-, -N( R d )C(O)- alkylene group
• L5 is a (r+1)-valent alicyclic group which may have a heteroatom.
• the alicyclic group which may have a heteroatom is a group having the specific ring structure described above, and the preferred embodiments are also the same.
• L5 preferably contains a ring selected from the group consisting of a cyclopentane ring, a pyrrolidine ring, a cyclohexane ring, an adamantane ring, a piperidine ring, and the following fused rings, and more preferably contains an adamantane ring.
• the definition of R is as described above.
• L 4 and (-L 6 -Si(R) n L 3-n ) may be bonded to that one ring atom, or two (-L 6 -Si(R) n L 3-n ) may be bonded to that one ring atom. It is preferable that L 4 and (-L 6 -Si(R) n L 3-n ) are bonded to different ring atoms.
• the r (-L 6 -Si(R) n L 3-n ) may each be bonded to a different ring atom, two of which may be bonded to one ring carbon atom, and there may be two or more ring carbon atoms to which two (-L 6 -Si(R) n L 3-n ) are bonded.
• the remaining bonds are bonded to a hydrogen atom or a substituent.
• the remaining bonds are preferably bonded to a hydrogen atom or an alkyl group, and more preferably bonded to a hydrogen atom.
• the number of carbon atoms in the alkyl group is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1.
• each L6 is independently a single bond or a divalent linking group.
• the divalent linking group represented by L6 has the same meaning as the divalent linking group represented by L1 in the above formula (2), and preferred embodiments are also the same.
• the two or more L 6 s may be the same or different.
• L6 is preferably an alkylene group which may have an etheric oxygen atom.
• the number of carbon atoms in the alkylene group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 2 to 20, and may be 2 to 10, 2 to 6, or 2 to 5. Examples include 2, 3, 8, 9, and 11. The number of carbon atoms may be 1 to 10.
• r is an integer of 1 or more. r is preferably an integer of 1 to 15, more preferably an integer of 1 to 6, even more preferably an integer of 2 to 4, and particularly preferably an integer of 2 or 3.
• the multiple [-Si(R) n L 3-n ] may be the same or different from each other. From the viewpoint of availability of raw materials and ease of production of the compound, it is preferable that the multiple [-Si(R) n L 3-n ] are the same.
• the definition of L a is the same as that of L a in formula (3-1A-1), and the preferred embodiments are also the same.
• a 1 is a single bond, —C(O)NR 6 —, —C(O)—, —OC(O)O—, —NHC(O)O—, —NHC(O)NR 6 —, —O— or SO 2 NR 6 —.
• Q 14 When the atom in Z 1 to which Q 14 is bonded is a carbon atom, Q 14 is a single bond, an alkylene group, or a group having -C(O)NR 6 -, -C(O)-, -NR 6 - or O- between the carbon-carbon atom of an alkylene group having 2 or more carbon atoms; when the atom in Z 1 to which Q 14 is bonded is a nitrogen atom, Q 14 is a single bond (with the proviso that A 1 is -C(O)-), an alkylene group, a group having 2 or more carbon atoms and having -C(O)NR 6 -, -C(O)-, -NR 6 - or -O- between the carbon-carbon atom of an alkylene group, or a group having -C(O)- at the N-terminal of the alkylene group.
• Q 24 is an alkylene group, a group having -C(O)NR 6 -, -C(O)-, -NR 6 - or -O- between the carbon-to-carbon atom of an alkylene group having 2 or more carbon atoms, a group having -C(O)NR 6 -, -C(O)-, -NR 6 - or -O- at the end of the alkylene group not connected to Si, or a group having -C(O)NR 6 -, -C(O)-, -NR 6 - or -O- between the carbon-to-carbon atom of an alkylene group having 2 or more carbon atoms and having -C(O)NR 6 -, -C(O)-, -NR 6 - or -O- at the end of the alkylene group not connected to Si.
• the atom in Z1 to which Q24 is bonded is a nitrogen atom, it is an alkylene group, or a group having -C(O) NR6- , -C(O)-, -NR6- or O- between the carbon-carbon atoms of an alkylene group having 2 or more carbon atoms.
• the two or more Q24s may be the same or different.
• R6 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.
• the compound represented by formula (1-1) may be a compound represented by formula (4).
• L 9 represents a single bond, an alkylene group, -O-, -S-, -SO 2 -, -N(R d )-, -C(O)-, -Si(R a ) 2 -, -OC(O)-, -C(O)O-, -C(O)S-, -C(O)N(R d )-, -N(R d )C(O)-, -N(R d )C(O)N(R d )-, -N(R d )C(O)O-, -OC(O)N(R d )-, -SO 2 N(R d )-, -N(R d )SO 2 -, an alkylene group having -C(O)N(R d )C(O)-, -OC(O)N(R d )-, an alkylene group having an etheric oxygen atom,
• L8 is a divalent alicyclic group which may have a heteroatom.
• the divalent alicyclic group which may have a heteroatom is a group having the specific ring structure described above, and the preferred embodiments are also the same.
• L 8 preferably contains a ring selected from the group consisting of a cyclopentane ring, a cyclohexane ring, an adamantane ring, a piperidine ring, and the following fused rings, and more preferably contains an adamantane ring.
• the definition of R is as described above.
• the bond that does not constitute a ring of an atom that constitutes a specific ring structure possessed by L8 is a bond that is bonded to L7 or L9 .
• the remaining bond is bonded to a hydrogen atom or a substituent.
• the remaining bond is preferably bonded to a hydrogen atom or an alkyl group, and more preferably bonded to a hydrogen atom.
• the number of carbon atoms in the alkyl group is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1.
• L 10 is an (s+1)-valent alicyclic group which may have a heteroatom.
• the alicyclic group which may have a heteroatom is a group having the specific ring structure described above, and the preferred embodiments are also the same.
• L 10 preferably contains a ring selected from the group consisting of a cyclopentane ring, a pyrrolidine ring, a cyclohexane ring, an adamantane ring, a piperidine ring, and the following fused rings, and more preferably contains an adamantane ring.
• L 9 and (-L 11 -Si(R) n L 3-n ) may be bonded to that one ring atom, or two (-L 11 -Si(R) n L 3-n ) may be bonded to that one ring atom. It is preferable that L 9 and (-L 11 -Si(R) n L 3-n ) are bonded to different ring atoms.
• the s (-L 11 -Si(R) n L 3-n ) may each be bonded to a different ring atom, two of which may be bonded to one ring carbon atom, and there may be two or more ring carbon atoms to which two (-L 11 -Si(R) n L 3-n ) are bonded.
• the remaining bonds are bonded to a hydrogen atom or a substituent.
• the remaining bonds are preferably bonded to a hydrogen atom or an alkyl group, and more preferably bonded to a hydrogen atom.
• the number of carbon atoms in the alkyl group is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1.
• L 11 each independently represents a single bond or a divalent linking group.
• the divalent linking group represented by L 11 has the same meaning as the divalent linking group represented by L 1 in the above formula (2), and preferred embodiments are also the same.
• the two or more L 11 s may be the same or different.
• L 11 is preferably a single bond or an alkylene group which may have an etheric oxygen atom.
• the number of carbon atoms in the alkylene group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 2 to 20, and may be 2 to 10, 2 to 6, or 2 to 5. Examples include 2, 3, 8, 9, and 11. The number of carbon atoms may be 1 to 10.
• s is an integer of 1 or more. s is preferably an integer of 1 to 15, more preferably an integer of 1 to 6, still more preferably an integer of 1 to 4, and particularly preferably an integer of 1 to 3.
• the multiple [-Si(R) n L 3-n ] may be the same or different from each other. From the viewpoint of availability of raw materials and ease of production of the compound, it is preferable that the multiple [-Si(R) n L 3-n ] are the same.
• Examples of the compound represented by formula (1-1) include compounds of the following formula.
• the compounds of the following formula are preferred in that they are easy to produce industrially, easy to handle, and provide a surface treatment layer with even better light resistance.
• Rt in the compound of the following formula is the same as [T-O-(Si(R 2 ) 2 -O) m -Si(R 2 ) 2 ] in formula (1-1) described above, and the preferred forms are also the same.
• n in the compound of the following formula is 1 to 30, preferably 1 to 20, and more preferably 1 to 12.
• the compound (1-1) may be a compound in which L 1 is an alkylene group, L 2 is a specific ring structure, and L 3 is an alkylene group.
• the alkylene groups of L 1 and L 3 may be linear or branched, but linear is preferred.
• the number of carbon atoms of the alkylene groups in L 1 and L 3 is preferably 1 to 30, and may be 1 to 25, 1 to 20, 1 to 10, or 5 to 10.
• L 1 and L 3 may be alkylene groups having 1 to 10 or 5 to 10 carbon atoms
• L 2 may be a combination of a specific ring structure.
• q may be 1.
• Each R2 is independently a hydrocarbon group or a trialkylsilyloxy group;
• Each A is independently a (q+1)-valent linking group having an alicyclic structure which may have a heteroatom,
• Each R is independently a hydrocarbon group;
• Each L is independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group;
• m is a number equal to or greater than 0;
• n is independently an integer from 0 to 2,
• Each q is independently an integer of 1 or more.
• the compound (1-2) may be a compound in which L 1 is an alkylene group, L 2 is a specific ring structure, and L 3 is an alkylene group.
• the alkylene groups of L 1 and L 3 may be linear or branched, but linear is preferred.
• the number of carbon atoms of the alkylene groups in L 1 and L 3 is preferably 1 to 30, and may be 1 to 25, 1 to 20, 1 to 10, or 5 to 10.
• L 1 and L 3 may be alkylene groups having 1 to 10 or 5 to 10 carbon atoms
• L 2 may be a combination of a specific ring structure.
• q may be 1.
• the number average molecular weight (Mn) of the compound of the present disclosure is preferably from 500 to 20,000, more preferably from 600 to 18,000, and even more preferably from 700 to 15,000.
• Mn is 500 or more
• the light resistance of the surface treatment layer is more excellent.
• Mn is 20,000 or less
• the viscosity can be easily adjusted within an appropriate range, and the solubility is improved, so that the handling property during film formation is excellent.
• composition of the present disclosure is only required to contain the compound of the present disclosure, and components other than the compound of the present disclosure are not particularly limited. That is, the composition of the present disclosure may contain at least one of the compound represented by formula (1-1) and the compound represented by formula (1-2). The composition of the present disclosure may contain both the compound represented by formula (1-1) and the compound represented by formula (1-2). The composition of the present disclosure preferably contains the compound of the present disclosure and a liquid medium. When the composition of the present disclosure contains 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 may contain the compound of the present disclosure, and may contain impurities such as by-products produced in the production process of the compound of the present disclosure.
• the content of the compound of the present disclosure is preferably 0.001 to 40 mass%, more preferably 0.01 to 20 mass%, and even more preferably 0.1 to 10 mass%, based on the total amount of the composition of the present disclosure.
• the content of the compound of the present disclosure is preferably 0.01 to 10 mass%, more preferably 0.02 to 5 mass%, even more preferably 0.03 to 3 mass%, and particularly preferably 0.05 to 2 mass%, based on the total amount of the composition of the present disclosure.
• the liquid medium contained in the composition of the present disclosure may be only one type, or may be two or more types.
• the liquid medium is preferably an organic solvent.
• organic solvents include compounds consisting of only hydrogen atoms and carbon atoms, and compounds consisting of only hydrogen atoms, carbon atoms, and oxygen atoms.
• specific examples include hydrocarbon organic solvents, ketone organic solvents, ether organic solvents, ester organic solvents, glycol organic solvents, and alcohol organic solvents. Among these, ester organic solvents are preferred.
• hydrocarbon organic solvent examples include pentane, hexane, heptane, octane, hexadecane, isohexane, isooctane, isononane, cycloheptane, cyclohexane, bicyclohexyl, benzene, toluene, ethylbenzene, o-xylene, m-xylene, p-xylene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, n-butylbenzene, sec-butylbenzene, and tert-butylbenzene.
• ketone organic solvent examples include acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, 2-heptanone, 4-heptanone, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, and isophorone.
• ether-based organic solvent examples include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, and 1,4-dioxane.
• ester-based organic solvent examples include methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate, tert-butyl acetate, amyl acetate, isoamyl acetate, ethyl 3-ethoxypropionate, ethyl lactate, ethylene glycol monobutyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, dipropylene glycol methyl ether acetate, 3-methoxy-3-methylbutyl acetate, 3-methoxybutyl acetate, propylene glycol monomethyl acetate, propylene glycol dimethyl acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether, Examples of the monoisobutyl
• 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, ethylene glycol mono-2-ethylhexyl ether, diethylene glycol mono-2-ethylhexyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monopropyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-tert-butyl ether, ethylene glycol monopropyl ether, ethylene glycol monomethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monomethyl ether, dipropyl
• ethylene glycol dimethyl ether examples include glycol monopropyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol monophenyl ether, 1,3-butylene glycol, propylene glycol n-propyl ether, propylene glycol n-butyl ether, diethylene glycol monoethyl ether, dipropylene glycol n-propyl ether, dipropylene glycol n-butyl ether, tripropylene glycol methyl ether, tripropylene glycol n-butyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol dibutyl ether, tetraethylene glycol dimethyl
• the alcohol-based organic solvent 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, cyclohexanol,
• organic solvents include halogen-based organic solvents, fluorine-containing organic solvents, nitrogen-containing compounds, sulfur-containing compounds, and siloxane compounds other than the compounds disclosed herein.
• some of the oxygen atoms in the siloxane skeleton may be replaced with a divalent hydrocarbon group.
• the divalent hydrocarbon group include alkylene groups such as methylene, ethylene, propylene, and butylene.
• the terminal silicon atom of the siloxane skeleton-containing group may have a hydrolyzable group, a hydrocarbon group (preferably an alkyl group) or the like bonded thereto.
• 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 upper limit of the number of elements is preferably 10 or more.
• examples of the hydrolyzable group represented by X b5 include the same hydrolyzable group represented by L in formula (1-1) above, a cyano group, a hydrogen atom, and an allyl group, and an alkoxy group or an isocyanato group is preferable.
• the alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms.
• X b5 is preferably a hydrolyzable group.
• 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 reactive silyl groups at both ends of a divalent organic group, that is, a bissilane.
• examples of the hydrolyzable group 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, and an alkoxy group or an isocyanato group is preferable.
• the alkoxy group an alkoxy group having 1 to 4 carbon atoms is preferable, and a methoxy group or an ethoxy group is more preferable.
• X b6 and X b7 may be the same group or different groups. From the viewpoint of availability, X b6 and X b7 are preferably the same group.
• Y b1 is a divalent organic group linking the reactive silyl groups at both ends.
• the divalent organic group Y b1 preferably has 1 to 8 carbon atoms, and more preferably has 1 to 3 carbon atoms.
• Examples of Y b1 include an alkylene group, a phenylene group, and an alkylene group having an ether oxygen atom between carbon atoms.
• Examples of compounds represented by formula (M3) include ( CH3O ) 3Si ( CH2 ) 2Si ( OCH3 ) 3 , ( C2H5O)3Si(CH2)2Si(OC2H5)3, (OCN)3Si(CH2)2Si(NCO)3 , Cl3Si ( CH2 ) 2SiCl3 , ( CH3O ) 3Si ( CH2 ) 6Si ( OCH3 ) 3 , and ( C2H5O ) 3Si ( CH2 ) 6Si (OC2H5 ) 3 .
• composition disclosed herein is useful for coating applications because it contains a liquid medium, and can be used as a coating liquid.
• composition of the present disclosure may contain other components other than 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 base catalysts that promote the hydrolysis and condensation reaction of hydrolyzable silyl groups.
• the content of other components in the present surface treatment agent is preferably 10% by mass or less, and more preferably 1% by mass or less.
• the content of the compound represented by formula (5) is preferably 50 mass% or less, and more preferably 40 mass% or less.
• the surface treatment layer may be formed on a part of the surface of the substrate, or may be formed on the entire surface of the substrate.
• the surface treatment layer may be spread on the surface of the substrate in the form of a film, or may be scattered in the form of dots.
• the compound of the present disclosure is contained in a state in which partial or total hydrolysis of reactive silyl groups ((Si(R) n L 3-n )) has progressed and a dehydration condensation reaction of silanol groups has progressed.
• the thickness of the surface treatment layer is preferably 1 to 100 nm, and more preferably 1 to 50 nm. If the thickness of the surface treatment layer is 1 nm or more, the effect of the surface treatment is likely to be sufficient. If the thickness of the surface treatment layer is 100 nm or less, the utilization efficiency is high.
• the thickness of the surface treatment layer can be calculated from the vibration period of the interference pattern obtained by obtaining an interference pattern of reflected X-rays by X-ray reflectivity method using a thin film analysis X-ray diffractometer (product name "ATX-G", manufactured by RIGAKU Corporation).
• the type of the substrate is not particularly limited, and may be, for example, a substrate that is required to be imparted with water repellency.
• the substrate include a substrate that may be used by contacting with other articles (e.g., a stylus) or human fingers; a substrate that may be held by human fingers during operation; and a substrate that may be placed on top of other articles (e.g., a mounting table).
• the material of the substrate include metal, resin, glass, sapphire, ceramic, semiconductor, stone, fiber, nonwoven fabric, paper, wood, fur, natural leather, artificial leather, ceramics, and composite materials thereof. Glass may be chemically strengthened.
• the substrate may be a building material, a decorative building material, an interior item, a transport device (e.g., an automobile), a sign, a bulletin board, a drinking vessel, a tableware, an aquarium, an ornamental device (e.g., a frame, a box), a laboratory device, a furniture, a textile product, a packaging container; a glass or a resin used in art, sports, a game, etc.; a glass or a resin used in the exterior part (excluding the display part) of a device such as a mobile phone (e.g., a smartphone), a personal digital assistant, a game machine, a remote control, etc.
• the shape of the substrate may be a plate or a film.
• a substrate for a touch panel As the substrate, a substrate for a touch panel, a substrate for a display, or a lens for glasses is suitable, and a substrate for a touch panel is particularly suitable.
• a substrate for a touch panel As the material for the substrate for a touch panel, glass or a transparent resin is preferred.
• the substrate may be a substrate having one or both surfaces subjected to a surface treatment such as corona discharge treatment, plasma treatment, or plasma graft polymerization treatment.
• a substrate having been subjected to a surface treatment has better adhesion to the surface treatment layer, and the light resistance of the surface treatment layer is improved. For this reason, it is preferable to perform a surface treatment on the surface of the substrate that comes into contact with the surface treatment layer.
• a base layer which will be described later, is provided on the substrate having been subjected to a surface treatment, the adhesion to the base layer is better, and the light resistance of the surface treatment layer is improved. For this reason, when a base layer is provided, it is preferable to perform a surface treatment on the surface of the substrate that comes into contact with the base layer.
• the surface treatment layer may be provided directly on the surface of the substrate, or a base layer may be provided between the substrate and the surface treatment layer.
• the article of the present disclosure preferably includes a substrate, a base layer disposed on the substrate, and a surface treatment layer that is surface-treated with the surface treatment agent of the present disclosure and disposed on the base layer.
• the underlayer is preferably a layer containing an oxide containing silicon and at least one specific element selected from the group consisting of Group 1 elements, Group 2 elements, Group 4 elements, Group 5 elements, Group 13 elements, and Group 15 elements of the periodic table.
• Group 1 elements of the periodic table refer to lithium, sodium, potassium, rubidium, and cesium.
• Group 1 elements lithium, sodium, and potassium are preferred, and sodium and potassium are more preferred, from the viewpoint of being able to form a surface treatment layer on the underlayer more uniformly without defects, or of further suppressing variation in the composition of the underlayer between samples.
• the underlayer may contain two or more types of Group 1 elements.
• Group 2 elements of the periodic table refer to beryllium, magnesium, calcium, strontium, and barium.
• magnesium, calcium, and barium are preferred, and magnesium and calcium are more preferred, from the viewpoint of being able to form a surface treatment layer on the underlayer more uniformly without defects, or from the viewpoint of further suppressing variation in the composition of the underlayer between samples.
• the underlayer may contain two or more types of Group 2 elements.
• Group 4 elements of the periodic table refer to titanium, zirconium, and hafnium.
• Group 4 elements titanium and zirconium are preferred, and titanium is more preferred, from the viewpoint of being able to form a surface treatment layer on the underlayer more uniformly without defects, or from the viewpoint of further suppressing variation in the composition of the underlayer between samples.
• the underlayer may contain two or more types of Group 4 elements.
• Group 5 elements of the periodic table refer to vanadium, niobium, and tantalum.
• Group 5 elements vanadium is particularly preferred from the viewpoint of providing a surface treatment layer with superior light resistance.
• the underlayer may contain two or more Group 5 elements.
• Group 13 elements of the periodic table refer to boron, aluminum, gallium, and indium.
• Group 13 elements boron, aluminum, and gallium are preferred, and boron and aluminum are more preferred, from the viewpoint of being able to form a surface treatment layer on the underlayer more uniformly without defects, or of further suppressing variation in the composition of the underlayer between samples.
• the underlayer may contain two or more types of Group 13 elements.
• the Group 15 elements of the periodic table (hereinafter also referred to as "Group 15 elements") refer to nitrogen, phosphorus, arsenic, antimony, and bismuth.
• Group 15 elements from the viewpoint of being able to form a surface treatment layer on the underlayer more uniformly without defects, or from the viewpoint of further suppressing the variation in the composition of the underlayer between samples, phosphorus, antimony, and bismuth are preferred, and phosphorus and bismuth are more preferred.
• the underlayer may contain two or more types of Group 15 elements.
• Group 1 elements, Group 2 elements, and Group 13 elements are preferred because they provide a surface treatment layer with superior light resistance, Group 1 elements and Group 2 elements are more preferred, and Group 1 elements are even more preferred.
• the specific element may be one type of element or two or more types of elements.
• the oxide contained in the underlayer may be a mixture of oxides of the above elements (silicon and the specific element) alone (for example, a mixture of silicon oxide and an oxide of the specific element), a composite oxide containing two or more of the above elements, or a mixture of an oxide of the above elements alone and a composite oxide.
• the ratio of the total molar concentration of the specific elements in the underlayer to the molar concentration of silicon in the underlayer is preferably 0.02 to 2.90, more preferably 0.10 to 2.00, and 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 profile analysis using X-ray photoelectron spectroscopy (XPS) using ion sputtering.
• the underlayer may be a single layer or multiple layers.
• the underlayer may have an uneven surface.
• the thickness of the underlayer is preferably 1 to 100 nm, more preferably 1 to 50 nm, and even more preferably 2 to 20 nm. If the thickness of the underlayer is equal to or greater than the lower limit, the adhesion of the underlayer to the surface treatment layer is improved, and the light resistance of the surface treatment layer is more excellent. If the thickness of the underlayer is equal to or less than the upper limit, the light resistance of the underlayer itself is excellent. The thickness of the underlayer is measured by observing a cross section of the underlayer with a transmission electron microscope (TEM).
• TEM transmission electron microscope
• the undercoat layer can be formed, for example, by a deposition method using a deposition material or a wet coating method.
• the deposition material used in the deposition method preferably contains an oxide containing silicon and a specific element.
• Specific examples of the form of the deposition material include powder, melt, sintered body, granulated body, and crushed body, and from the viewpoint of handleability, the melt, sintered body, and granulated body are preferred.
• the melt means a solid obtained by melting the powder of the deposition material at a high temperature and then cooling and solidifying it.
• the sintered body means a solid obtained by firing the powder of the deposition material, and if necessary, a molded body may be used by pressing the powder instead of the powder of the deposition material.
• the granulated body means a solid obtained by kneading the powder of the deposition material with a liquid medium (e.g., water, organic solvent) to obtain particles, and then drying the particles.
• a liquid medium e.g., water, organic solvent
• the deposition material can be produced, for example, by the following method.
• a method of mixing a powder containing silicon e.g., powder made of silicon oxide, silica sand, silica gel
• a powder containing a specific element e.g., powder of an oxide, carbonate, sulfate, nitrate, oxalate, hydroxide of a specific element
• water e.g., water, drying the mixture, and then firing the dried mixture or a compact obtained by pressing the mixture to obtain a sintered body.
• silicon e.g., powder made of silicon oxide, silica sand, silica gel
• a specific element e.g., powder of an oxide, carbonate, sulfate, nitrate, oxalate, hydroxide of a specific element
• a specific example of a deposition method using a deposition material is a vacuum deposition method, in which a deposition material is evaporated in a vacuum chamber and attached to the surface of a substrate.
• the temperature during deposition (for example, the temperature of a boat in which a deposition material is placed when a vacuum deposition apparatus is used) is preferably 100 to 3,000°C, and more preferably 500 to 3,000°C.
• the pressure during deposition (for example, the pressure inside a tank in which a deposition material is placed when a vacuum deposition apparatus is used) is preferably 1 Pa or less, and more preferably 0.1 Pa or less.
• one deposition material may be used, or two or more deposition materials containing different elements may be used.
• the evaporation method of the deposition material include a resistance heating method in which the deposition material is melted and evaporated on a resistance heating boat made of a high melting point metal, and an electron gun method in which the deposition material is irradiated with an electron beam to directly heat the deposition material to melt and evaporate the surface.
• the electron gun method is preferred as the evaporation method of the deposition material because it can evaporate high melting point substances because it can heat locally, and because the areas not hit by the electron beam are at low temperature, there is no risk of reaction with the container or contamination with impurities.
• the evaporation method of the deposition materials may use multiple boats, or may use a single boat containing all the deposition materials.
• the deposition method may be co-deposition or alternating deposition.
• examples include a case where silica and a specific source are mixed in the same boat and used, a case where silica and a specific element source are placed in separate boats and co-deposited, and a case where they are placed in separate boats and alternately deposited.
• the deposition conditions, order, etc. are appropriately selected depending on the configuration of the underlayer.
• a base layer on a substrate it is preferable to form a base layer on a substrate by a wet coating method using a coating liquid that contains a silicon-containing compound, a compound containing a specific element, and a liquid medium.
• silicon compounds include silicon oxide, silicic acid, partial condensates of silicic acid, alkoxysilanes, and partial hydrolysis condensates of alkoxysilanes.
• the liquid medium may be the same as the liquid medium contained in the composition of the present disclosure.
• the article of the present disclosure may be an optical material having a surface treatment layer as the outermost layer.
• Preferred examples of the optical material include optical materials related to displays and the like, as well as a wide variety of other optical materials.
• optical materials include displays such as cathode ray tubes (CRTs; for example, personal computer monitors), liquid crystal displays, plasma displays, organic EL displays, inorganic thin-film EL dot matrix displays, rear projection displays, fluorescent display tubes (VFDs), and field emission displays (FEDs; Field Emission Displays), or protective plates for such displays, or displays whose surfaces have been treated with an anti-reflection film.
• Step 1-3 Synthesis of compound (C)>
• trimethylsilanol (0.19 g) and THF (5 mL) were added to a 100 mL three-neck flask and stirred at 25°C.
• the mixture was then cooled to 0°C, and a hexane solution (1.6 M, 0.9 mL) of n-BuLi (n-butyl lithium) was added dropwise.
• Step 1-4 Synthesis of compound (D)> Dichloromethane (10 g) and compound (C) (0.80 g) were added to a 100 mL flask and stirred at 25° C. Then, a toluene solution of platinum/1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3 mass%, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (0.40 g) were added and stirred at 25° C. for 2 hours. The solvent was distilled off from the reaction solution under reduced pressure to obtain 0.75 g of compound (D). The structure of compound (D) was confirmed by the following NMR data. In compound (D), the average value of n was 18.
• Step 2-4 Synthesis of compound (H)>
• trimethylsilanol (0.19 g) and THF (5 mL) were added to a 100 mL three-neck flask and stirred at 25°C. Then, the mixture was cooled to 0°C, and a hexane solution of n-BuLi (1.6 M, 0.9 mL) was added dropwise. Then, a THF solution of hexamethylcyclotrisiloxane (1.2 M, 1 mL) was added dropwise, and a THF solution of hexamethylcyclotrisiloxane (1.2 M, 9 mL) was added dropwise, and the mixture was stirred for 2 hours.
• compound (G) (1.28 g) was added, and the mixture was stirred at 25°C for 1 hour. Hexane and ion-exchanged water were added to the reaction solution in this order, and the mixture was separated, and the organic phase was separated. After the solvent and low boiling point components were distilled off from the organic phase under reduced pressure, flash column chromatography using silica gel (developing solvent: hexane/ethyl acetate) was performed to obtain 1.2 g of compound (H). The structure of compound (H) was confirmed by the following NMR data: In compound (H), the average value of n was 18.
• Step 2-5 Synthesis of Compound (I)> Compound (H) (3.2 g), 10% palladium-carbon (50% water content, 320 mg), and THF (15 mL) were added to a 100 mL flask under a hydrogen atmosphere, and the mixture was stirred at 25° C. for 4 hours. Insoluble matter was filtered out from the reaction solution, and the solvent of the filtrate was distilled off under reduced pressure to obtain 2.9 g of compound (I). The structure of compound (I) was confirmed by the following NMR data. In compound (I), the average value of n was 18.
• Step 2-7 Synthesis of compound (K)> Dichloromethane (10 g) and compound (J) (0.80 g) were added to a 100 mL flask and stirred at 25° C. A toluene solution of platinum/1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3 mass%, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (0.40 g) were added and stirred at 25° C. for 2 hours. The solvent was distilled off from the reaction solution under reduced pressure to obtain 0.75 g of compound (K). The structure of compound (K) was confirmed from the following NMR data. In compound (K), the average value of n was 18.
• Step 3-2 Synthesis of compound (M)>
• trimethylsilanol (0.19 g) and THF (5 mL) were added to a 100 mL three-neck flask and stirred at 25°C. Then, the mixture was cooled to 0°C, and a hexane solution of n-BuLi (1.6 M, 0.9 mL) was added dropwise. Then, a THF solution of hexamethylcyclotrisiloxane (1.2 M, 1 mL) was added dropwise, and a THF solution of hexamethylcyclotrisiloxane (1.2 M, 9 mL) was added dropwise, and the mixture was stirred for 2 hours.
• compound (L) (1.28 g) was added, and the mixture was stirred for 1 hour. Hexane and ion-exchanged water were added successively to the reaction liquid, and the liquids were separated, and the organic phase was separated. After the solvent and low boiling point components were distilled off from the organic phase under reduced pressure, flash column chromatography using silica gel (developing solvent: hexane/ethyl acetate) was performed to obtain 1.2 g of compound (M). The structure of compound (M) was confirmed by the following NMR data: In compound (M), the average value of n was 18.
• Step 4-1 Synthesis of compound (P)> Compound (P) was obtained in the same manner as in Step 2-1 of Example 2, except that 3-oxo-5 ⁇ -cholanic acid (5.2 g) was used as the raw material instead of 3-hydroxy-4-adamantanecarboxylic acid. The structure of compound (P) was confirmed by the following NMR data.
• Step 4-3 Synthesis of compound (R)> Except for using compound (Q) instead of compound (F), the same procedures as in steps 2-3 to 2-7 of Example 2 were carried out to obtain 0.8 g of compound (R). The structure of compound (R) was confirmed by the following NMR data. In compound (R), the average value of n was 18.
• the hearth was heated to about 2000° C., and silicon oxide was vacuum-deposited on the surface of the substrate, to prepare a substrate with a silicon oxide layer having a thickness of about 20 nm.
• the substrate with the silicon oxide layer was placed on the sample stage of a spray coater (API-90RS manufactured by Apiros Co., Ltd.) so that the silicon oxide layer was on the surface.
• 13 g of a heptane solution containing 0.2 mass % of the compound obtained in each example was placed in a syringe in the spray coater, and spray-coated at an atomization pressure of 130 kPa, a nozzle-to-sample surface distance of 50 mm, and a scanning speed of 300 mm/sec (wet coating method).
• the light intensity at 200-800 nm was measured using an intensity meter (VEGA, manufactured by OPHIL) and found to be 200 mW/ cm2 .
• the sample was irradiated with uniform light from the mercury lamp for 100 hours in an atmospheric environment with a temperature of 20 to 40°C and a humidity of 30 to 75%.
• the water contact angle of the sample after irradiation was measured in the same manner as the initial contact angle, and the arithmetic mean value calculated from the measured values was taken as the water contact angle after light irradiation.
• the evaluation criteria for light resistance are as follows. A: The difference in water contact angle before and after irradiation was less than 5°. B: The difference in water contact angle before and after irradiation was 5° or more and less than 10°. C: The difference in water contact angle before and after irradiation was 10° or more.
• Examples 1 to 4 and 101 to 104 are working examples, and Examples 5 and 105 are comparative examples.
• the "alicyclic structure” column of “compound” indicates the alicyclic structure possessed by the compound synthesized in each example.
• “fused ring A” means “4-azatricyclo[5.2.1.0 2,6 ]decane ring”
• “fused ring B” means "hexadecahydro-1H-cyclopenta[a]phenanthrene ring.”
• compound (S) synthesized in Example 5 does not have an alicyclic structure, and therefore "none" is entered in the "alicyclic structure” column.
• the compounds disclosed herein are useful as surface treatment agents.
• the surface treatment agent can be used, for example, for display devices such as touch panel displays, optical elements, semiconductor elements, building materials, automobile parts, and substrates in nanoimprint technology.
• the surface treatment agent can also be used for bodies, window glass (front glass, side glass, rear glass), mirrors, bumpers, and the like in transport devices such as trains, automobiles, ships, and aircraft.
• the surface treatment agent can also be used for outdoor items such as building exterior walls, tents, solar power generation modules, soundproofing boards, and concrete; fishing nets, insect nets, and aquariums.
• the surface treatment agent can also be used for various indoor equipment such as kitchens, bathrooms, washstands, mirrors, and toilet peripheral parts; ceramics such as chandeliers and tiles; and artificial marble and air conditioners.
• the surface treatment agent can also be used as an anti-fouling treatment for jigs, inner walls, piping, and the like in factories.
• the surface treatment agent can also be used for goggles, glasses, helmets, pachinko machines, fibers, umbrellas, playground equipment, and soccer balls.
• the surface treatment agent can also be used as an anti-adhesion agent for various packaging materials such as food packaging materials, cosmetic packaging materials, the inside of pots, etc.
• the surface treatment agent can also be used for car navigation systems, mobile phones, smartphones, digital cameras, digital video cameras, PDAs, portable audio players, car audio, game machines, eyeglass lenses, camera lenses, lens filters, sunglasses, medical equipment such as gastroscopes, copiers, PCs, displays (e.g., liquid crystal displays, organic EL displays, plasma displays, touch panel displays), touch panels, protective films, anti-reflection films, and other optical components.
• displays e.g., liquid crystal displays, organic EL displays, plasma displays, touch panel displays), touch panels, protective films, anti-reflection films, and other optical components.

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