CN110741054A - Composition for forming hydrophilic coating film, and hydrophilic coating film using same - Google Patents
Composition for forming hydrophilic coating film, and hydrophilic coating film using same Download PDFInfo
- Publication number
- CN110741054A CN110741054A CN201880039328.0A CN201880039328A CN110741054A CN 110741054 A CN110741054 A CN 110741054A CN 201880039328 A CN201880039328 A CN 201880039328A CN 110741054 A CN110741054 A CN 110741054A
- Authority
- CN
- China
- Prior art keywords
- coating film
- hydrophilic coating
- group
- carbon atoms
- forming
- Prior art date
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- Granted
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- 239000011248 coating agent Substances 0.000 title claims abstract description 68
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- 239000000178 monomer Substances 0.000 claims abstract description 31
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 27
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 16
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 12
- 239000003960 organic solvent Substances 0.000 claims abstract description 12
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- 239000002184 metal Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- 150000004703 alkoxides Chemical class 0.000 claims description 22
- 239000000758 substrate Substances 0.000 claims description 13
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- 239000006228 supernatant Substances 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- YZVRVDPMGYFCGL-UHFFFAOYSA-N triacetyloxysilyl acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)OC(C)=O YZVRVDPMGYFCGL-UHFFFAOYSA-N 0.000 description 1
- GYZQBXUDWTVJDF-UHFFFAOYSA-N tributoxy(methyl)silane Chemical compound CCCCO[Si](C)(OCCCC)OCCCC GYZQBXUDWTVJDF-UHFFFAOYSA-N 0.000 description 1
- OAVPBWLGJVKEGZ-UHFFFAOYSA-N tributoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCCCC)(OCCCC)OCCCC)CCC2OC21 OAVPBWLGJVKEGZ-UHFFFAOYSA-N 0.000 description 1
- MYWQGROTKMBNKN-UHFFFAOYSA-N tributoxyalumane Chemical compound [Al+3].CCCC[O-].CCCC[O-].CCCC[O-] MYWQGROTKMBNKN-UHFFFAOYSA-N 0.000 description 1
- UCSBCWBHZLSFGC-UHFFFAOYSA-N tributoxysilane Chemical compound CCCCO[SiH](OCCCC)OCCCC UCSBCWBHZLSFGC-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- MMZPUXVBQAQQDQ-UHFFFAOYSA-N triethoxy(2-pyridin-4-ylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC1=CC=NC=C1 MMZPUXVBQAQQDQ-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- UNKMHLWJZHLPPM-UHFFFAOYSA-N triethoxy(oxiran-2-ylmethoxymethyl)silane Chemical compound CCO[Si](OCC)(OCC)COCC1CO1 UNKMHLWJZHLPPM-UHFFFAOYSA-N 0.000 description 1
- SJQPASOTJGFOMU-UHFFFAOYSA-N triethoxy-[1-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)C(C)OCC1CO1 SJQPASOTJGFOMU-UHFFFAOYSA-N 0.000 description 1
- NFRRMEMOPXUROM-UHFFFAOYSA-N triethoxy-[1-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)C(CC)OCC1CO1 NFRRMEMOPXUROM-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- RWJUTPORTOUFDY-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)CCOCC1CO1 RWJUTPORTOUFDY-UHFFFAOYSA-N 0.000 description 1
- CFUDQABJYSJIQY-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CC(C)OCC1CO1 CFUDQABJYSJIQY-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- LFBULLRGNLZJAF-UHFFFAOYSA-N trimethoxy(oxiran-2-ylmethoxymethyl)silane Chemical compound CO[Si](OC)(OC)COCC1CO1 LFBULLRGNLZJAF-UHFFFAOYSA-N 0.000 description 1
- DAVVOFDYOGMLNQ-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)C(C)OCC1CO1 DAVVOFDYOGMLNQ-UHFFFAOYSA-N 0.000 description 1
- FNBIAJGPJUOAPB-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)C(CC)OCC1CO1 FNBIAJGPJUOAPB-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- OZWKZRFXJPGDFM-UHFFFAOYSA-N tripropoxysilane Chemical compound CCCO[SiH](OCCC)OCCC OZWKZRFXJPGDFM-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- C—CHEMISTRY; METALLURGY
- 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
- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Paints Or Removers (AREA)
Abstract
hydrophilic coating film-forming compositions containing a betaine-containing composition represented by the formula [1]]The siloxane monomer contains water or an organic solvent, and the betaine group has + charge on a nitrogen atom in a nitrogen-containing heterocyclic structure. (R)1: c1-5 alkyl, R2: c1-5 alkyl, etc., p: 1-3, q: 0-2 when p is 1, 0-1 when p is 2, 0 when p is 3, L: a linear or branched alkylene group having 1 to 20 carbon atoms and optionally having a hetero atom, wherein X: single bond, etc., Y: comprisesA 2-valent organic group of a nitrogen-containing heterocycle, wherein M is a linear or branched alkylene group having 1 to 10 carbon atoms and bonded to the nitrogen atom in Y, and any of M and L forms N by bonding to the nitrogen atom in Y+Moiety, Z: COO (carbon organic compound)‑、SO3 ‑Etc.)
Description
Technical Field
The present invention relates to a composition for forming a hydrophilic coating film having a hydrophilic surface and an antifogging effect, and a hydrophilic coating film using the same.
Background
The surface properties required for the base material include antifogging properties, antistatic properties, antifouling properties, biocompatibility, and the like. These surface characteristics are usually achieved by imparting hydrophilicity to the surface of the base material by coating (covering) a hydrophilic coating or the like.
As polymers capable of imparting hydrophilicity to a substrate, for example, a polymer of methacrylate containing a phosphoryl group (see patent document 1), a compound obtained by introducing a functional group capable of forming a covalent bond with an inorganic base material into a compound having a betaine group having a very strong interaction with water (see patent document 2), and the like are known.
However, these materials have a problem that the surface properties such as hydrophilicity and antifogging property are gradually or rapidly deteriorated by storage under high-temperature and high-humidity conditions.
Documents of the prior art
Patent document
Patent document 1: japanese laid-open patent publication No. 6-313009
Disclosure of Invention
Problems to be solved by the invention
The present invention has been made in view of the above problems, and an object of the present invention is to provide a composition for forming a hydrophilic coating film, which does not deteriorate surface characteristics such as hydrophilicity and antifogging property even when stored under high-temperature and high-humidity conditions, and a hydrophilic coating film obtained therefrom.
Means for solving the problems
Therefore, the present invention has the following gist.
[1] hydrophilic coating film-forming compositions containing a siloxane monomer having a betaine group having a positive (+) charge on a nitrogen atom in a nitrogen-containing heterocyclic structure and containing water or an organic solvent.
[2] A method for forming a hydrophilic coating film, comprising applying the above-mentioned composition for forming a hydrophilic coating film on a substrate to form a coating film, and drying and baking the coating film to obtain a coating film.
[3] kinds of hydrophilic coating films, which are obtained from the above-described composition for forming a hydrophilic coating film.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, a hydrophilic coating film-forming composition and a hydrophilic coating film obtained therefrom can be provided, in which hydrophilicity and antifogging properties are not deteriorated even when stored under high-temperature and high-humidity conditions.
The hydrophilic coating film obtained from the composition for forming a hydrophilic coating film of the present invention can be used for a water-droplet-preventing film, an antifogging film, and the like for lenses such as glasses and cameras, windows of buildings, cars, and the like.
Detailed Description
The hydrophilic coating film-forming composition of the present invention is characterized by containing a siloxane monomer having a betaine group having a positive (+) charge on a nitrogen atom in a nitrogen-containing heterocyclic structure (hereinafter, also referred to as a specific siloxane monomer) and containing water or an organic solvent.
< specific Silicone monomer >
The hydrophilic coating film-forming composition of the present invention contains a siloxane monomer having a betaine group having a + charge on a nitrogen atom in a nitrogen-containing heterocyclic structure.
Betaine refers to a compound having a positive charge and a negative charge at positions not adjacent to each other in the molecule, and a dissociable hydrogen atom is not bonded to an atom having a positive charge and has no charge as the whole molecule.
The positive charge of the betaine group contained in a particular siloxane monomer is present at the nitrogen atom on the nitrogen-containing heterocycle. Examples of the nitrogen-containing heterocycle include pyridine, piperidine, imidazole, oxazole, thiazole, pyrazole, imidazoline, pyrazine, benzimidazole, quinoline, isoquinoline, purine, quinoxaline and the like, and pyridine or imidazoline is preferable.
The specific siloxane monomer is represented by the following general formula.
The above formula [1]In, R1Represents an alkyl group having 1 to 5 carbon atoms, preferably 1 to 3 carbon atoms.
R2Represents an alkyl group having 1 to 5 carbon atoms, preferably 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, or an alkynyl group having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms. R2Any hydrogen atom in the ring is optionally substituted with a halogen atom such as an alkyl group having 1 to 5 carbon atoms or a fluorine atom, an aromatic ring, or an aliphatic ring. p represents an integer of 1 to 3. q represents an integer of 0 to 2 when p is 1, an integer of 0 to 1 when p is 2, or 0 when p is 3.
L represents a linear or branched alkylene group having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, which may have a hetero atom. Any hydrogen atom of the alkylene group is optionally substituted with a halogen atom, an aromatic ring or an aliphatic ring, such as an alkyl group having 1 to 5 carbon atoms, preferably 1 to 4 carbon atoms, or a fluorine atom. Among them, a linear or branched alkylene group having 2 to 7 carbon atoms, preferably 2 to 6 carbon atoms is preferable. Here, the hetero atom means oxygen, nitrogen, sulfur, or phosphorus, preferably oxygen, nitrogen, or sulfur.
X represents a single bond, -O-, -COO-, -OCO-, -CONR3-、-NR4-CO-, or-NR5＝NR6-。R3、R4、R5、R6Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, preferably 1 to 3 carbon atoms.
Y represents a 2-valent organic group containing a nitrogen-containing heterocycle. Examples of the compound include pyridine, piperidine, imidazole, oxazole, thiazole, pyrazole, imidazoline, pyrazine, benzimidazole, quinoline, isoquinoline, purine, quinoxaline, and the like, and pyridine or imidazoline is preferable.
M represents a linear or branched alkylene group having 1 to 10 carbon atoms, preferably 1 to 8 carbon atoms, any hydrogen atom of the alkylene group being optionally substituted by a halogen atom such as an alkyl group having 1 to 5 carbon atoms, preferably 1 to 4 carbon atoms, or a fluorine atom, wherein a linear or branched alkylene group having 2 to 7 carbon atoms, preferably 2 to 6 carbon atoms is preferred, M is bonded to the nitrogen atom of Y, and any of M and L forms N by bonding to the nitrogen atom of Y+And (4) partial.
Z represents COO-、SO3 -Or PO4 -. From the viewpoint of durability of the resulting coating film, SO is preferred3 -。
Specific examples of specific siloxane monomers are shown below, but the siloxane monomers are not limited to these.
In the formula, Me represents a methyl group and Et represents an ethyl group. With respect to N+Moieties, also including tautomers.
Among these, the following monomers are preferred as the specific siloxane monomer from the viewpoint of stability of the monomer and availability of raw materials.
< Process for producing specific Silicone monomer >
The specific siloxane monomer used in the present invention can be produced by reacting a sultone ring compound such as 1, 3-propane sultone, 1, 4-butane sultone, or 2, 4-butane sultone with a silicon compound containing a nitrogen-containing heterocyclic structure, for example, in the case of a sulfonic acid terminal.
The carboxylic acid terminal compound can be obtained by reacting a lactone ring compound such as β -propiolactone with a silicon compound containing a nitrogen-containing heterocyclic structure, or by adding acrylic acid to a silicon compound containing a nitrogen-containing heterocyclic structure.
Examples of the reaction solvent include water, alcohols (e.g., methanol, ethanol, and 2-propanol), aprotic polar organic solvents (e.g., dimethylformamide, dimethylsulfoxide, dimethylacetamide, and N-methylpyrrolidone), ethers (e.g., diethyl ether, diisopropyl ether, tert-butyl methyl ether, cyclopentyl methyl ether, tetrahydrofuran, and dioxane), aliphatic hydrocarbons (e.g., pentane, hexane, heptane, and petroleum ether), aromatic hydrocarbons (e.g., benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, nitrobenzene, and tetralin), halogen hydrocarbons (e.g., chloroform, dichloromethane, carbon tetrachloride, and dichloroethane), lower fatty acid esters (e.g., methyl acetate, ethyl acetate, butyl acetate, and methyl propionate), and nitriles (e.g., acetonitrile, propionitrile, and butyronitrile). These solvents can be suitably selected in consideration of the ease of reaction, and 1 kind thereof may be used alone or 2 or more kinds thereof may be used in combination. In addition, the solvent may be used as a solvent not containing water by using a suitable dehydrating agent or drying agent, depending on the case.
Preferred solvents include acetonitrile and tetrahydrofuran.
The reaction time is 30 minutes to 180 hours, preferably 2 to 120 hours, and particularly preferably 5 to 100 hours.
The silicon compound containing a nitrogen-containing heterocyclic structure as a raw material may be a commercially available compound or may be easily obtained by a known method. The reaction temperature is preferably from 0 ℃ to the boiling point of each solvent, more preferably from 0 ℃ to 120 ℃, and particularly preferably from 5 ℃ to 100 ℃.
When the specific siloxane monomer as the reaction product is precipitated in the reaction organic solvent, the purification can be carried out by a method of filtering or drying. When the reaction is carried out in a uniform system all the time, the obtained reaction product may be used as it is, but when the target specific siloxane monomer is a solid, it may be separated and purified by a known method such as crystallization or reprecipitation by adding a poor solvent after concentrating the reaction solvent.
< other ingredients >
The composition for forming a hydrophilic coating film of the present invention may further contain at least 1 or more selected from the group consisting of a metal alkoxide, a metal alkoxide oligomer, a metal alkoxide polymer, inorganic fine particles, a leveling agent, and a surfactant, in addition to the specific siloxane monomer, water, or an organic solvent.
The metal alkoxide is contained to improve mechanical stability of the formed coating film, and examples of the metal alkoxide include silicon, titanium, aluminum, tantalum, antimony, bismuth, tin, indium, zinc, and the like. Among these, silicon, titanium, or zirconium is preferable from the viewpoint of availability.
Examples of the metal alkoxide include metal alkoxides represented by the following formula (II) or (III).
M1(OR2)n (II)
In the formula (II), R2Represents an alkyl group or acetyl group having 1 to 5 carbon atoms, preferably 1 to 3 carbon atoms. n represents an integer of 2 to 5. M1Silicon (Si), titanium (Ti), zirconium (Zr), or aluminum (Al) is preferable, and silicon (Si) or titanium (Ti) is particularly preferable. In addition, n is preferably 3 or 4.
R3 xM1(OR2)4-x(III)
In the formula (III), M1、R2As defined above for formula (I). R3Is a hydrogen atom or a group selected from the group consisting of a halogen atom, a vinyl group, a styryl group, a phenyl group, a naphthyl group, and an alkyl group having 1 to 30 carbon atoms which is optionally substituted with an acryloyl group, a methacryloyl group, or an aryl group and which optionally contains a hetero atom. x is an integer of 1 to 3. Here, the heteroatom is oxygen, nitrogen, sulfur or phosphorus, preferably oxygen, nitrogen or sulfur.
Examples of the metal alkoxide represented by the above formula (II) include silicon alkoxides such as tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, tetrabutoxysilane, and tetraacetoxysilane, titanium alkoxides such as titanium tetraethoxide, titanium tetrapropoxide, and titanium tetrabutoxide, zirconium tetraalkoxide such as zirconium tetraethoxide, zirconium tetrapropoxide, and zirconium tetrabutoxide, aluminum trialkoxide compounds such as aluminum tributoxide, aluminum triisopropoxide, and aluminum triethoxide, and tantalum pentaalkoxide such as tantalum pentapropoxide, and tantalum pentabutoxide. These may be used alone or in combination of 2 or more.
M of the above formula (III)1Is silicon and R3Examples of the hydrogen atom include trimethoxysilane, triethoxysilane, tripropoxysilane and tributoxysilane. These may be used alone or in combination of 2 or more.
M of the above formula (III)1Is silicon and R3In the case of an organic group, for example, methyltrimethoxysilane, methyltripropoxysilane, methyltriacetoxysilane, methyltributoxysilane, methyltripentoxysilane, methyltriphenoxysilane, methyltribenzyloxysilane, methyltriphylethoxysilane, glycidoxymethyltrimethoxysilane, glycidoxymethyltriethoxysilane, α -glycidoxyethyltrimethoxysilane, α -glycidoxyethyltriethoxysilane, α 0-glycidoxyethyltrimethoxysilane, β -glycidoxyethyltriethoxysilane, α -glycidoxypropyltrimethoxysilane, α -glycidoxypropyltriethoxysilane, β -glycidoxypropyltrimethoxysilane, β -glycidoxypropyltriethoxysilane, gamma-glycidoxypropyltrimethoxysilane, gamma-glycidoxypropyltriethoxysilane, gamma-glycidoxypropyltributoxysilane, gamma-glycidoxypropyltrimethoxysilane, gamma-glycidoxypropyltriethoxysilane, gamma-glycidoxypropyltrimethoxysilane, α -glycidoxybutyloxytrimethoxysilane, α -butoxybutyltrimethoxysilane, β -glycidoxypropyltrimethoxysilane, gamma-butylpropoxytrimethoxysilane, gamma-glycidoxypropyltrimethoxysilane, gamma-butylpropoxytrimethoxysilane, delta-glycidoxypropyltrimethoxysilane, gamma-butyltrimethoxysilane, gamma-butylpropoxytrimethoxysilane, β -glycidoxypropyltrimethoxysilane, delta-butyltrimethoxysilane, gamma-butylpropoxytrimethoxysilane, delta-glycidoxypropyltrimethoxysilane, gamma-butyltrimethoxysilane, delta-butyltrimethoxysilane, gamma-butyl(3, 4-epoxycyclohexyl) methyltrimethoxysilane, (3, 4-epoxycyclohexyl) methyltriethoxysilane, β - (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, β - (3, 4-epoxycyclohexyl) ethyltriethoxysilane, β - (3, 4-epoxycyclohexyl) ethyltripropyloxysilane, β - (3, 4-epoxycyclohexyl) ethyltributyloxysilane, β - (3, 4-epoxycyclohexyl) ethyltriphenoxysilane, gamma- (3, 4-epoxycyclohexyl) propyltrimethoxysilane, gamma- (3, 4-epoxycyclohexyl) propyltriethoxysilane, delta- (3, 4-epoxycyclohexyl) butyltrimethoxysilane, delta- (3, 4-epoxycyclohexyl) butyltriethoxysilane, glycidoxymethyldimethoxymethyldimethoxysilane, glycidoxymethyldiethoxymethyldiethoxysilane, β -glycidoxyethylmethyldimethoxysilane, α -glycidoxyethylmethyldiethoxymethyldiethoxysilane, β -glycidoxyethylmethyldimethoxysilane, β -glycidoxyethyldimethoxysilane, 3-glycidyloxyethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, gamma-glycidoxypropyldimethoxydimethoxydimethoxysilane, gamma-glycidoxypropyltrimethoxysilane, gamma-glycidoxypropylmethyldimethylethyl-glycidoxypropyltrimethoxysilane, gamma-glycidoxypropylSilane, N- (β -aminoethyl) γ -aminopropyltriethoxysilane, N- (β -aminoethyl) γ -aminopropylmethyldiethoxysilane, dimethyldimethoxysilane, phenylmethyldimethoxysilane, dimethyldiethoxysilane, phenylmethyldiethoxysilane, γ -chloropropylmethyldimethoxysilane, γ -chloropropylmethyldiethoxysilane, dimethyldiacetoxysilane, γ -mercaptopropylmethyldimethoxysilane, γ -mercaptomethyldiethoxysilane, γ -ureidopropyltriethoxysilane, γ -ureidopropyltrimethoxysilane, γ -ureidopropyltripropoxysilane, (R) -N-1-phenylethyl-N '-triethoxysilylpropylurea, (R) -N-1-phenylethyl-N' -trimethoxysilylpropylurea, 3-isocyanatopropyltriethoxysilane, trifluoropropyltrimethoxysilane, bromopropyltriethoxysilane, diethyldiethoxysilane, diethyldimethoxysilane, trimethylethoxysilane, trimethylmethoxysilane and the like, these may be used alone or in combination of 2 or more.
The metal alkoxide oligomer and the metal alkoxide polymer are contained for the purpose of improving the mechanical stability of the formed coating film. As these metals, single or composite oxide precursors of silicon, titanium, aluminum, tantalum, antimony, bismuth, tin, indium, zinc, and the like can be used. The metal alkoxide oligomer or metal alkoxide polymer may be a commercially available product or may be obtained from a monomer such as a metal alkoxide by a conventional method such as hydrolysis.
Specific examples of commercially available metal alkoxide oligomers and metal alkoxide polymers include siloxane oligomers such as Methyl silicate 51, Methyl silicate 53A, Ethyl silicate 40, Ethyl silicate 48, EMS-485, and SS-101 manufactured by COLCOATCCO., LTD, siloxane polymers, and titanyl oligomers such as titanium n-butoxide tetramer manufactured by KANTO CHEMICAL CO., LTD. These may be used alone or in combination of 2 or more.
The leveling agent, the surfactant and the like are contained for the purpose of improving the uniformity of the coating film, and known ones can be used, and commercially available products are particularly preferred because of their easy availability.
The inorganic fine particles are preferably silica fine particles, alumina fine particles, titania fine particles, magnesium fluoride fine particles, and the like, and particularly preferably a colloidal solution of these inorganic fine particles. The colloidal solution may be one in which inorganic fine particle powder is dispersed in a dispersion medium, or may be a commercially available colloidal solution.
The inorganic fine particles preferably have an average particle diameter of 0.001 to 0.2 μm, and further preferably 0.001 to 0.1 μm in the step, and when the average particle diameter exceeds 0.2 μm, the transparency of the cured coating formed using the prepared coating liquid may be reduced, and the average particle diameter is 50% volume average particle diameter (D50).
Examples of the dispersion medium for the inorganic fine particles include water and an organic solvent. The colloidal solution is preferably adjusted to have a pH or pKa of preferably 1 to 10, more preferably 2 to 7, from the viewpoint of stability of the coating liquid for forming a coating film.
Examples of the organic solvent used in the dispersion medium of the inorganic fine particles include alcohols such as methanol, ethanol, propanol, butanol, ethylene glycol, propylene glycol, butylene glycol, pentanediol, 2-methyl-2, 4-pentanediol, diethylene glycol, dipropylene glycol, and ethylene glycol monopropyl ether; ketones such as methyl ethyl ketone and methyl isobutyl ketone; aromatic hydrocarbons such as toluene and xylene; amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone; esters such as ethyl acetate, butyl acetate, and γ -butyrolactone; ethers such as tetrahydrofuran and 1, 4-dioxane. Among them, alcohols or ketones are preferable. These organic solvents may be used alone or in combination of 2 or more as a dispersion medium.
Among the other components optionally contained, preferred are metal alkoxides, metal oxide sols, or metal alkoxide oligomers in which the portion of the alkoxy group is optionally substituted with other organic groups.
The content of the metal alkoxide, metal oxide sol, or metal alkoxide oligomer in the composition of the present invention is 0.5 to 100 parts by mass, preferably 1 to 60 parts by mass, per 100 parts by mass of the specific siloxane monomer, and if the content is within the above range, the hydrophilicity and film stability of the composition of the present invention can be further exhibited in step .
< composition for Forming hydrophilic coating film >
The composition for forming a hydrophilic coating film of the present invention is a solution obtained by mixing a specific siloxane monomer with 1 or 2 or more kinds of water or organic solvents.
Examples of the organic solvent include alcohols such as methanol, ethanol, 2-propanol, butanol, diacetone alcohol and trifluoroethanol, ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, glycols such as ethylene glycol, diethylene glycol, propylene glycol and hexylene glycol, methyl cellosolve, ethyl cellosolve, butyl cellosolve, ethyl carbitol, butyl carbitol, ethylene glycol monomethyl ether, ethylene glycol dimethyl ether, ethylene glycol N-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, propylene glycol monomethyl ether and propylene glycol monobutyl ether, glycol ethers such as methyl acetate, ethyl acetate and ethyl lactate, esters such as N-methyl-2-pyrrolidone, N-dimethylformamide, N-dimethylacetamide, γ -butyrolactone, dimethyl sulfoxide, tetramethylurea, hexamethylphosphoric triamide, and the like, M-cresol, and the like.
Among them, from the viewpoint of solubility of the monomer, preferred as the organic solvent are alcohols such as methanol, ethanol, 2-propanol, and trifluoroethanol, glycols such as ethylene glycol, propylene glycol, and hexylene glycol, methyl cellosolve, ethyl cellosolve, butyl cellosolve, ethyl carbitol, butyl carbitol, ethylene glycol monomethyl ether, ethylene glycol dimethyl ether, ethylene glycol N-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, propylene glycol monomethyl ether, and propylene glycol monobutyl ether, and glycol ethers such as N-methyl-2-pyrrolidone.
The specific siloxane monomers contained in the above solution may be hydrolyzed. Acids such as hydrochloric acid, sulfuric acid, nitric acid, acetic acid, formic acid, oxalic acid, and maleic acid; and a catalyst such as an alkali such as ammonia, methylamine, ethylamine, ethanolamine or triethylamine, or a metal salt such as hydrochloric acid, sulfuric acid or nitric acid.
When the hydrolysis is carried out, the reaction temperature is preferably from 0 ℃ to boiling point, more preferably from 0 ℃ to 120 ℃, particularly preferably from 5 ℃ to 80 ℃. The reaction time is preferably 10 minutes to 80 hours, more preferably 30 minutes to 50 hours, and particularly preferably 30 minutes to 2 hours.
In the present invention, the solution obtained by the above method may be used as it is as a composition for forming a coating layer, or the solution obtained by the above method may be concentrated, diluted with a solvent or replaced with another solvent as necessary.
The solvent used in this case is not particularly limited as long as the silicon compound is uniformly dissolved, and or more kinds thereof can be arbitrarily selected and used.
The content of the specific siloxane monomers in the composition of the invention is SiO2The concentration is preferably 0.005 to 15% by mass, more preferably 0.01 to 12% by mass in terms of solid content, and when the concentration is in the above-mentioned range, a desired film thickness can be easily obtained by times of application, and a sufficient pot life of the solution can be easily obtained.
< film formation >
The composition for forming a hydrophilic coating film of the present invention can be formed into a hydrophilic coating film on a substrate by applying a known coating method. Examples of the coating method include a dip coating method, a spin coating method, a spray coating method, a flow coating method, a brush coating method, a bar coating method, a gravure coating method, a roll transfer method, a blade coating method, an air knife coating method, a slit coating method, a screen printing method, an ink jet method, and a flexographic printing method. Among them, a spin coating method, a slit coating method, a blade coating method, a spray coating method, or a dip coating method is preferable.
< substrate >
Examples of the substrate include glass, plastics { polymethyl methacrylate, polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, ABS, polycarbonate, polystyrene, epoxy resin, unsaturated polyester, melamine, diallyl phthalate, polyimide, urethane, nylon, polyethylene, polypropylene, cycloolefin polymer, polyvinyl chloride, fluororesin (polytetrafluoroethylene resin, polychlorotrifluoroethylene resin, polyvinylidene fluoride resin, polyvinyl fluoride resin, perfluoroalkoxy fluororesin, tetrafluoroethylene-hexafluoropropylene copolymer resin, ethylene-tetrafluoroethylene copolymer resin, ethylene-chlorotrifluoroethylene copolymer resin, etc.), polybutadiene, polyisoprene, SBR, nitrile rubber, EPM, EPDM, epichlorohydrin rubber, neopentylene rubber, polyethylene terephthalate, polyethylene naphthalate, polypropylene, etc, Polysulfide, butyl rubber, etc.), metals (iron, aluminum, stainless steel, titanium, copper, brass, alloys thereof, etc.), cellulose derivatives, cellulose analogs (chitin, chitosan, metalloporphyrin (Porphyran), etc.), natural fibers (silk, cotton, etc.), etc., and the like.
In addition, if necessary, the substrate may be subjected to a surface activation treatment (a method of increasing the surface energy of the substrate surface) such as a primer treatment, a vacuum plasma, an atmospheric pressure plasma, a corona discharge treatment, a flame treatment, an ITRO treatment, an ultraviolet irradiation, or an ozone treatment in advance in order to improve the adhesiveness with the substrate or the like.
< drying >
The hydrophilic coating film of the present invention can be obtained by drying and baking the coating film of the hydrophilic coating film-forming composition formed on the substrate. The drying step is preferably carried out at a temperature ranging from room temperature to 150 ℃, more preferably from 40 ℃ to 120 ℃. The time is preferably about 30 seconds to 10 minutes, and more preferably about 1 to 8 minutes. As the drying method, a hot plate, a hot air circulation type oven, or the like is preferably used.
< firing >
In the firing step, the temperature is preferably in the range of 80 to 300 ℃ and more preferably in the range of 100 to 250 ℃ in view of heat resistance and environment of the substrate. The time is preferably 5 minutes or longer, and more preferably 15 minutes or longer. As the firing method, a hot plate, a thermal cycle oven, an infrared oven, or the like is preferably used.
The thickness of the coating film obtained by the above method can be selected as needed. The thickness of the coating is preferably 3 to 150nm in order to easily obtain the stability of the hydrophilic coating. More preferably 5 to 120 nm.
Examples
The present invention will be described in more detail below with reference to examples, but the present invention is not limited thereto.
The following abbreviations are as follows.
DHIMES: triethoxy-3- (2-imidazolin-1-yl) propylsilane
p-PyTES: 2- (4-pyridylethyl) triethoxysilane
DMAPS: 3- (N, N-dimethylaminopropyl) trimethoxysilane
MTES: methyltriethoxysilane
TFE: trifluoroethanol
The products in the following synthesis examples were identified by 1H-NMR analysis. The analysis conditions were as follows.
The device comprises the following steps: varian NMR System 400NB (400MHz)
And (3) determination of a solvent: CDCl3、DMSO-d6、
Reference substance: tetramethylsilane (TMS) (1H. delta. 0.0ppm)
< synthetic example 1: synthesis of A-1 >
Acetonitrile (398.9g) and DHIMES (199.5g, 727mmol) were charged into a reactor, and 1, 3-propanesultone (97.7g) dissolved in acetonitrile (299.3g) was added dropwise under a nitrogen atmosphere and ice-cooling conditions using a dropping funnel.
After the dropwise addition, the remaining components remaining on the dropping funnel were rinsed with acetonitrile (99.8g), and the reaction was allowed to proceed at room temperature for 18 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give 459g of total internal weight in the reaction vessel, and tetrahydrofuran (1596g) was added to precipitate crystals, followed by filtration and drying to obtain 244.0g (yield: 85%) of A-1 (white crystals).
1H-NMR (400MHz) in CDCl3The method comprises the following steps: 0.57-0.61ppm (m, 2H), 1.23ppm (t, J ═ 7.2Hz, 9H), 1.69-1.76ppm (m, 2H), 2.14-2.21ppm (m, 2H)2.90ppm(t，J＝7.2Hz，2H)，3.57ppm(t，J＝7.2Hz，2H)，3.78-3.85ppm(m，8H)，3.93-3.99ppm(m，4H)，8.82ppm(s，1H)
< synthetic example 2: synthesis of A-2
40.5g (property: red crystal) of A-2 (yield 74%) was obtained in the same manner as in Synthesis example 1, except that p-PyTES was used as a siloxane monomer.
< synthetic example 3: synthesis of A-3
49.4g (property: white crystal) of A-3 (yield 82%) was obtained in the same manner as in Synthesis example 1, except that DMAPS was used as the siloxane monomer.
< Synthesis example 4: synthesis of A-4 >
DHIMES (20.0g, 72.9mmol) was put into acetonitrile (30.1g), 1, 4-butane sultone (11.0g) was added under nitrogen atmosphere at room temperature, then, a reaction was carried out at 45 ℃ for about 2 days to disappear the raw materials, after the reaction was completed, the solvent was removed by concentration under reduced pressure, ethyl acetate (20.0g) and hexane (20.0g) were added to prepare a suspension, the suspension was placed in a freezer at-25 ℃ for to precipitate crystals, and the crystals were collected by filtration under nitrogen atmosphere, and the obtained crystals were washed with hexane (50.0g) slurry, filtered and dried to obtain 20.2g A-4 (light yellow crystals) (yield: 67%).
< Synthesis example 5: synthesis of A-5
Triethoxy-3- (2-imidazolin-1-yl) propylsilane (20.0g, 72.9mmol) was charged into acetonitrile (40.0g), and 2, 4-butanesultone (10.4g) was added under ice-cooling in a nitrogen atmosphere. Subsequently, the reaction was carried out at room temperature for about 1 day to remove the starting materials. After the reaction was completed, the solvent was removed by concentration under reduced pressure. Subsequently, the concentrated solution was diluted with ethyl acetate (80.0g), and hexane (80.0g) was added to prepare a suspension. The viscous material was solidified in a freezer at-25 ℃ and the supernatant was removed. Ethyl acetate (70.0g) and hexane (70.0g) were again added to prepare a suspension, which was again placed in a freezer at-25 ℃ to precipitate crystals. 28.2g (yield: 94%) of A-5 (white crystal) was obtained by filtering under a nitrogen atmosphere, washing with hexane and drying.
< preparation example 1>
A200 mL flask was charged with 39.7g A-1 and 36.4g TFE, and stirred to dissolve A-1. A mixture of 0.3g of oxalic acid, 5.4g of water and 18.2g of TFE was added thereto, and the mixture was stirred at room temperature for 2 hours to obtain solution AA.
In a 500mL flask, 2.5g of AA and 297.5g of TFE were mixed, and the mixture was stirred at room temperature for 30 minutes to obtain a solution (K1).
< preparation example 2>
In a 200mL flask, 39.1g A-2 and 36.7g TFE were added and stirred to dissolve A-2. A mixture of 0.3g of oxalic acid, 5.4g of water and 18.4g of TFE was added thereto, and the mixture was stirred at room temperature for 2 hours to obtain a solution AB.
In a 500mL flask, 2.5g of solution AB and 297.5g of TFE were mixed, and the mixture was stirred at room temperature for 30 minutes to obtain a solution (K2).
< preparation example 3>
A200 mL flask was charged with 27.8g A-1, 5.3g MTES, and 40.8g TFE, and stirred to dissolve A-1 and MTES. A mixture of 0.3g of oxalic acid, 5.4g of water and 20.4g of TFE was added thereto, and the mixture was stirred at room temperature for 2 hours to obtain a solution AC.
In a 500mL flask, 2.5g of solution AC and 297.5g of TFE were mixed, and the mixture was stirred at room temperature for 30 minutes to obtain a solution (K3).
< preparation example 4>
A200 mL flask was charged with 32.9g A-3 and 40.9g of TFE, and stirred to dissolve A-3. A mixture of 0.3g of oxalic acid, 5.4g of water and 20.5g of TFE was added thereto, and the mixture was stirred at room temperature for 2 hours to obtain solution AD.
In a 500mL flask, 2.5g of AD and 297.5g of TFE were mixed, and the mixture was stirred at room temperature for 30 minutes to obtain a solution (K4).
< preparation example 5>
A100 mL flask was charged with 16.4g A-4 and 14.2g of TFE, and stirred to dissolve A-3. A mixture of 0.1g of oxalic acid, 2.2g of water and 7.1g of TFE was added thereto, and the mixture was stirred at room temperature for 2 hours to obtain a solution AE.
In a 500mL flask, 2.5g of AE and 297.5g of TFE were mixed, and the mixture was stirred at room temperature for 30 minutes to obtain a solution (K5).
< preparation example 6>
A100 mL flask was charged with 16.4g A-5 and 14.2g TFE, and stirred to dissolve A-3. A mixture of 0.1g of oxalic acid, 2.2g of water and 7.1g of TFE was added thereto, and the mixture was stirred at room temperature for 2 hours to obtain solution AF.
In a 500mL flask, 2.5g of AF solution and 297.5g of TFE were mixed, and the mixture was stirred at room temperature for 30 minutes to obtain a solution (K6).
< method of film formation >
The solutions K1 to K6 obtained in preparation examples 1 to 6 were subjected to pressure filtration using a membrane filter having a pore size of 0.5 μm, and a film was formed on a glass substrate by a spin coating method. The substrate was dried on a hot plate at 70 ℃ for 3 minutes, and then fired in a hot air circulation oven at 200 ℃ for 30 minutes to obtain a hydrophilic coating film.
The hydrophilic coatings (KL1 to KL5) of the solutions K1 to K3 and K5 to K6 obtained in preparation examples 1 to 3 and 5 to 6 were used as examples 1 to 5. The hydrophilic coating (KM1) of solution K4 obtained in preparation example 4 was defined as comparative example 1.
The following tests were carried out on the coatings (KL1 to KL5) of examples 1 to 3 and 5 to 6 and the coating (KM1) of comparative example 1, and the results are shown in table 1.
< Water contact Angle >
The contact angle at 1. mu.l of dropwise added pure water was measured using an automatic contact angle meter CA-Z model manufactured by Kyowa Kagaku K.K.
< high temperature and high humidity test >
The above-mentioned coatings (KL 1-KL 5 and KM1) were aged for 3 days in a high-temperature high-humidity oven at 60 ℃ and a relative humidity of 90%. Then, the water contact angle was measured by the above method.
< Water immersion test >
The respective coatings (KL1 to KL5 and KM1) were ultrasonically cleaned with pure water at room temperature for 5 minutes, and then dried in a hot air circulating oven at 80 ℃ for 10 minutes. Then, the high temperature and high humidity test was performed.
< breath test >
The films (KL1 to KL5, KM1) subjected to the water immersion test and the high temperature and high humidity test were subjected to air blowing, and the surface of the film was evaluated as ○ and the surface of the film was as x.
[ Table 1]
The coatings of examples 1 to 5 maintained hydrophilicity even after the high temperature and high humidity test and after the water immersion test, and also maintained antifogging properties as seen from the results of the expiration test. The coating film of comparative example 1 was degraded in hydrophilicity after 3 days of high temperature and high humidity by the water immersion test, and the surface of the coating film was fogged and degraded in antifogging property in the exhalation test.
The entire contents of the specification, claims, drawings, and abstract of japanese patent application No. 2017-117151, filed on 14/6/2017, are incorporated herein by reference as disclosure of the specification of the present invention.
Claims (14)
- hydrophilic coating film-forming compositions containing a siloxane monomer having a betaine group having a positive (+) charge on a nitrogen atom in a nitrogen-containing heterocyclic structure and containing water or an organic solvent.
- 2. The composition for forming a hydrophilic coating film according to claim 1, wherein the siloxane monomer is represented by the following formula [1],
formula [1]In, R1Represents an alkyl group having 1 to 5 carbon atoms,R2represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkynyl group having 2 to 5 carbon atoms, R2Optionally substituted with an alkyl group having 1 to 5 carbon atoms, a halogen atom, an aromatic ring or an aliphatic ring, p represents an integer of 1 to 3, q represents an integer of 0 to 2 when p is 1, an integer of 0 to 1 when p is 2, or 0 when p is 3,l represents a linear or branched alkylene group having 1 to 20 carbon atoms and optionally having a hetero atom, any hydrogen atom of the alkylene group being optionally substituted by an alkyl group having 1 to 5 carbon atoms, a halogen atom, an aromatic ring or an aliphatic ring,x represents a single bond, -O-, -COO-, -OCO-, -CONR3-、-NR4-CO-, or-NR5＝NR6-，R3、R4、R5And R6Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,y represents a 2-valent organic group having a nitrogen-containing heterocycle,m represents a linear or branched alkylene group having 1 to 10 carbon atoms, any hydrogen atom of the alkylene group is optionally substituted by an alkyl group having 1 to 5 carbon atoms or a halogen atom, M is bonded to a nitrogen atom of Y, and any of M and L forms N by bonding to a nitrogen atom of Y+In part (a) of the above-described embodiments,z represents COO-、SO3 -Or PO4 -。 - 3. The composition for forming a hydrophilic coating film according to claim 1 or 2, wherein Y is selected from the group consisting of pyridine, piperidine, imidazole, oxazole, thiazole, pyrazole, imidazoline, pyrazine, benzimidazole, quinoline, isoquinoline, purine, and quinoxaline.
- 4. The composition for forming a hydrophilic coating film according to any of claims 1 to 3, wherein Y is selected from the group consisting of pyridine, imidazole, imidazoline, and benzimidazole.
- 5. The hydrophilic coating film-forming composition according to any of claims 1 to 4, wherein the siloxane monomer is at least 1 selected from the group consisting of,
- 6. the hydrophilic coating film-forming composition according to any of claims 1 to 4, wherein the siloxane monomer is at least 1 selected from the group consisting of,
- 7. the composition according to any of claims 1 to 6, wherein SiO is used2The siloxane monomer having a betaine group is contained in an amount of 0.005 to 12 mass% in terms of solid content.
- 8. The composition for forming a hydrophilic coating film according to any of claims 1 to 7, further comprising a metal alkoxide, a metal alkoxide oligomer, or a metal alkoxide polymer.
- 9. The composition according to any of claims 1 to 8, further comprising inorganic fine particles, a leveling agent, or a surfactant.
- 10. A method for forming a hydrophilic coating film, comprising applying the composition for forming a hydrophilic coating film according to any of claims 1 to 9 onto a substrate to form a coating film, and drying and baking the coating film to obtain a coating film.
- 11. The method for forming a hydrophilic coating according to claim 10, wherein the coating film is dried at a temperature of from room temperature to 150 ℃ and baked at a temperature of from 80 ℃ to 300 ℃.
- 12. The method for forming a hydrophilic coating according to claim 10 or 11, wherein the thickness of the fired coating film is 3 to 150 nm.
- 13, hydrophilic coating films, which are obtained from the composition for forming a hydrophilic coating film according to any of claims 1 to 9.
- 14. The hydrophilic coating film according to claim 13, which is a water-droplet adhesion-preventing film or an antifogging film.
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| JP2017-117151 | 2017-06-14 | ||
| PCT/JP2018/022268 WO2018230514A1 (en) | 2017-06-14 | 2018-06-11 | Hydrophilic-coating-film forming composition and hydrophilic coating film using same |
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| CN113372109A (en) * | 2021-05-18 | 2021-09-10 | 景德镇陶瓷大学 | Preparation method of large-area defect-free nano-scale thickness compact ceramic film and ceramic film prepared by same |
| CN113512058A (en) * | 2021-08-10 | 2021-10-19 | 中国科学院深圳先进技术研究院 | Zwitterionic liquid silane coupling agent, synthetic method and application thereof |
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| JP7396827B2 (en) * | 2019-07-22 | 2023-12-12 | 花王株式会社 | How to treat hard surfaces |
| JP7435418B2 (en) | 2020-11-20 | 2024-02-21 | 信越化学工業株式会社 | Organosilicon compounds, their hydrolyzed condensates and coating compositions |
| JP2022128066A (en) | 2021-02-22 | 2022-09-01 | 東京応化工業株式会社 | Surface treatment liquid and hydrophilizing treatment method |
| WO2022180817A1 (en) * | 2021-02-26 | 2022-09-01 | 日本精化株式会社 | Sulfobetaine group-containing organosilicon compound and method for producing same |
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| CN1833010A (en) * | 2003-08-12 | 2006-09-13 | Nkm涂料株式会社 | Coating composition, antifouling coating film, underwater structure, and method of preventing fouling of underwater structure |
| CN102655953A (en) * | 2009-12-17 | 2012-09-05 | 3M创新有限公司 | Sulfonate-functional coatings and methods |
| CN104903363A (en) * | 2012-10-19 | 2015-09-09 | 夏普株式会社 | Monomer, liquid crystal composition, liquid crystal display device, and production method for liquid crystal display device |
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| JP2008239949A (en) | 2007-02-28 | 2008-10-09 | Fujifilm Corp | Composition for forming hydrophilic membrane and hydrophilic member |
| JP5315787B2 (en) * | 2008-05-19 | 2013-10-16 | 住友化学株式会社 | Imidazolium salt and particulate oxide on which it is immobilized |
| KR101610562B1 (en) * | 2011-07-27 | 2016-04-07 | 닛산 가가쿠 고교 가부시키 가이샤 | Liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display element |
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| CN1833010A (en) * | 2003-08-12 | 2006-09-13 | Nkm涂料株式会社 | Coating composition, antifouling coating film, underwater structure, and method of preventing fouling of underwater structure |
| CN102655953A (en) * | 2009-12-17 | 2012-09-05 | 3M创新有限公司 | Sulfonate-functional coatings and methods |
| CN104903363A (en) * | 2012-10-19 | 2015-09-09 | 夏普株式会社 | Monomer, liquid crystal composition, liquid crystal display device, and production method for liquid crystal display device |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113372109A (en) * | 2021-05-18 | 2021-09-10 | 景德镇陶瓷大学 | Preparation method of large-area defect-free nano-scale thickness compact ceramic film and ceramic film prepared by same |
| CN113512058A (en) * | 2021-08-10 | 2021-10-19 | 中国科学院深圳先进技术研究院 | Zwitterionic liquid silane coupling agent, synthetic method and application thereof |
| WO2023015797A1 (en) * | 2021-08-10 | 2023-02-16 | 中国科学院深圳先进技术研究院 | Zwitterionic liquid silane coupling agent, synthesis method, and use thereof |
| CN113512058B (en) * | 2021-08-10 | 2023-10-03 | 中国科学院深圳先进技术研究院 | Zwitterionic liquid silane coupling agent, synthetic method and application thereof |
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