WO2016068138A1 - 透明皮膜 - Google Patents
透明皮膜 Download PDFInfo
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- WO2016068138A1 WO2016068138A1 PCT/JP2015/080264 JP2015080264W WO2016068138A1 WO 2016068138 A1 WO2016068138 A1 WO 2016068138A1 JP 2015080264 W JP2015080264 W JP 2015080264W WO 2016068138 A1 WO2016068138 A1 WO 2016068138A1
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- Prior art keywords
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- compound
- transparent film
- molecular chain
- hydrolyzable
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- MYWQGROTKMBNKN-UHFFFAOYSA-N tributoxyalumane Chemical compound [Al+3].CCCC[O-].CCCC[O-].CCCC[O-] MYWQGROTKMBNKN-UHFFFAOYSA-N 0.000 description 1
- JWRQFDQQDBJDHD-UHFFFAOYSA-N tributoxyindigane Chemical compound CCCCO[In](OCCCC)OCCCC JWRQFDQQDBJDHD-UHFFFAOYSA-N 0.000 description 1
- WDVUXWDZTPZIIE-UHFFFAOYSA-N trichloro(2-trichlorosilylethyl)silane Chemical compound Cl[Si](Cl)(Cl)CC[Si](Cl)(Cl)Cl WDVUXWDZTPZIIE-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- MCXZOLDSEPCWRB-UHFFFAOYSA-N triethoxyindigane Chemical compound [In+3].CC[O-].CC[O-].CC[O-] MCXZOLDSEPCWRB-UHFFFAOYSA-N 0.000 description 1
- OPVRXFLDMSPNDD-UHFFFAOYSA-N triethyl trimethylsilyl silicate Chemical compound CCO[Si](OCC)(OCC)O[Si](C)(C)C OPVRXFLDMSPNDD-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- FGPUIKFYWJXRBX-UHFFFAOYSA-N trimethoxyindigane Chemical compound [In+3].[O-]C.[O-]C.[O-]C FGPUIKFYWJXRBX-UHFFFAOYSA-N 0.000 description 1
- IAORIIYGIHOPHS-UHFFFAOYSA-N trimethyl trimethylsilyl silicate Chemical compound CO[Si](OC)(OC)O[Si](C)(C)C IAORIIYGIHOPHS-UHFFFAOYSA-N 0.000 description 1
- AAPLIUHOKVUFCC-UHFFFAOYSA-N trimethylsilanol Chemical compound C[Si](C)(C)O AAPLIUHOKVUFCC-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YRLOGOACXRTJNE-UHFFFAOYSA-N tripropyl trimethylsilyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)O[Si](C)(C)C YRLOGOACXRTJNE-UHFFFAOYSA-N 0.000 description 1
- XAASNKQYFKTYTR-UHFFFAOYSA-N tris(trimethylsilyloxy)silicon Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)O[Si](C)(C)C XAASNKQYFKTYTR-UHFFFAOYSA-N 0.000 description 1
- GAAKLDANOSASAM-UHFFFAOYSA-N undec-10-enoic acid;zinc Chemical compound [Zn].OC(=O)CCCCCCCCC=C GAAKLDANOSASAM-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 210000002268 wool Anatomy 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- GAWWVVGZMLGEIW-GNNYBVKZSA-L zinc ricinoleate Chemical compound [Zn+2].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O.CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O GAWWVVGZMLGEIW-GNNYBVKZSA-L 0.000 description 1
- 229940100530 zinc ricinoleate Drugs 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229940118257 zinc undecylenate Drugs 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- 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
- C07F7/1804—Compounds having Si-O-C 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
- C09D183/14—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
-
- 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
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- 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
- C08G77/04—Polysiloxanes
-
- 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
- C08G77/50—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 by carbon linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
-
- 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
- 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
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
Definitions
- the present invention relates to a transparent film capable of imparting water repellency to various substrates.
- droplets adhere to the surface of the substrate, resulting in contamination and corrosion of the substrate, and further from this contamination and corrosion. Problems such as performance degradation may occur. Therefore, in these fields, it is required that the substrate surface has good water repellency, and in particular, it not only prevents the droplet from adhering to the substrate surface but also facilitates the removal of the adhered droplet. It is also required to be.
- Patent Document 1 discloses that co-hydrolysis and polycondensation of organosilane and metal alkoxide in a solution containing an organic solvent and water. Has been proposed.
- an object of the present invention is to achieve both water repellency, heat resistance, and light resistance (hereinafter referred to as “weather resistance” in combination of heat resistance and light resistance).
- the transparent film according to the present invention is a transparent film comprising a polysiloxane skeleton and a trialkylsilyl group-containing molecular chain bonded to a part of silicon atoms among silicon atoms forming the polysiloxane skeleton,
- the alkyl group in the trialkylsilyl group-containing molecular chain may be replaced with a fluoroalkyl group.
- the initial contact angle of the droplet on the transparent film is A 0, and the contact angle after standing at a temperature of 200 ° C. for 24 hours is
- B L the contact angle after irradiating a xenon lamp with B H and an intensity of 250 W at a temperature for 100 hours.
- the transparent film of the present invention is a transparent film comprising a polysiloxane skeleton and a trialkylsilyl group-containing molecular chain bonded to a part of silicon atoms among silicon atoms forming the polysiloxane skeleton.
- the alkyl group in the silyl group-containing molecular chain may be replaced with a fluoroalkyl group, and the initial contact angle of the droplet on the transparent film is A 1 , and the light of a mercury lamp having an emission line in the region of 300 nm or less is irradiated on the irradiation surface.
- the trialkylsilyl group-containing molecular chain is preferably represented by the following formula (s1).
- R s1 each independently represents a hydrocarbon group or a trialkylsilyloxy group. However, when all of R s1 are hydrocarbon groups, these hydrocarbon groups are alkyl groups.
- R s2 represents a dialkylsiloxane chain, and the oxygen atom of the dialkylsiloxane chain may be replaced with a divalent hydrocarbon group, and a methylene group (—CH 2 —) as a part of the divalent hydrocarbon group. May be replaced by an oxygen atom.
- * Represents a bond with a silicon atom.
- the trialkylsilyl group-containing molecular chain is preferably represented by the following formula (s1-1).
- the transparent film of the present invention preferably has a structure (B) represented by the following formula (2).
- R b1 represents a siloxane skeleton-containing group, a hydroxy group or an —O— group
- Z b1 represents a hydrolyzable group, a hydroxy group or an —O— group
- a plurality of formulas (2) R b1 and Z b1 may be the same or different.
- M represents a trivalent or tetravalent metal atom capable of forming a metal alkoxide.
- j represents an integer of 0 or 1 depending on M.
- the M is preferably Al, Si, Ti or Zr, and more preferably Si.
- the abundance ratio of the structure (B) and the structure (A) in which the trialkylsilyl group-containing molecular chain is bonded to the silicon atom (structure (B) / structure (A)) is a molar ratio. It is preferably 0.1 or more and 80 or less on the basis.
- the initial contact angle of the droplet on the transparent film of the present invention is preferably 95 ° or more.
- a coating composition comprising (b) is also encompassed within the scope of the present invention.
- the metal compound (b) is at least one selected from the group consisting of a compound represented by the following formula (II-1) and a hydrolysis-condensation product thereof, It is also preferred that the molar ratio of b) to the organosilicon compound (a) (metal compound (b) / organosilicon compound (a)) is 10 or more.
- M represents a trivalent or tetravalent metal atom capable of forming a metal alkoxide.
- a b1 independently represents a hydrolyzable group.
- R b2 represents a siloxane skeleton-containing group, a hydrocarbon chain-containing group or a hydrolyzable group. When R b2 and Z b2 are a siloxane skeleton-containing group or a hydrocarbon chain-containing group, R b2 and Z b2 are the same. If Z b2 is a hydrolyzable group, R b2 and A b1 may be the same or different. R b2 and Z b2 may be the same or different among the plurality of formulas (II).
- Z b2 represents a siloxane skeleton-containing group, a hydrocarbon chain-containing group, or a hydrolyzable group.
- k represents an integer of 0 or 1 depending on M.
- the organosilicon compound (a) is a compound represented by the following formula (II).
- a a1 independently represents a hydrolyzable group.
- Z a2 represents a trialkylsilyl group-containing molecular chain, a hydrocarbon chain-containing group, a siloxane skeleton-containing group or a hydrolyzable group.
- Z a2 and A a1 are the same It may or may not be.
- R a and Z a2 may be the same or different among a plurality of formulas (I).
- R s3 each independently represents an alkyl group having 1 to 4 carbon atoms.
- R s4 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, and the methylene group (—CH 2 —) in R s4 may be replaced with an oxygen atom.
- R s5 independently represents an alkyl group having 1 to 4 carbon atoms.
- m1 and n1 each independently represents an integer of 0 or more. However, the order of existence of each repeating unit with subscripts n1 and m1 and enclosed in parentheses is arbitrary in the formula. ]
- a plurality of A a1 each independently represents a hydrolyzable group.
- Z a2 represents a trialkylsilyl group-containing molecular chain, a hydrocarbon chain-containing group, a siloxane skeleton-containing group or a hydrolyzable group.
- Z a2 and A a1 are the same It may or may not be.
- R a and Z a2 may be the same or different among a plurality of formulas (I).
- R s3 each independently represents an alkyl group having 1 to 4 carbon atoms.
- R s4 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, and the methylene group (—CH 2 —) in R s4 may be replaced with an oxygen atom.
- R s5 independently represents an alkyl group having 1 to 4 carbon atoms.
- m and n each independently represents an integer of 0 or more. However, the order of existence of each repeating unit with subscripts n1 and m1 and enclosed in parentheses is arbitrary in the formula. ]
- the transparent film of the present invention can achieve both water and oil repellency, light resistance and heat resistance because the change in contact angle before and after thermal history or before and after light irradiation is adjusted within a certain range.
- FIG. 1 shows the spectral irradiance of “SP-9 250DB” manufactured by USHIO INC.
- the transparent film of the present invention suppresses a change in contact angle before and after heat history or before and after light irradiation.
- the contact angle change is adjusted to a specific range to provide water and oil repellency. It has been found that a transparent film capable of achieving both light resistance and heat resistance can be obtained.
- the transparent film of the present invention is a transparent film comprising a polysiloxane skeleton and a trialkylsilyl group-containing molecular chain bonded to a part of silicon atoms among silicon atoms forming the polysiloxane skeleton.
- the alkyl group in the silyl group-containing molecular chain may be replaced with a fluoroalkyl group.
- the initial contact angle of the droplet on the transparent film is A 0 , after standing at a temperature of 200 ° C. for 24 hours.
- the contact angle is B H and the contact angle after irradiating a xenon lamp with an intensity of 250 W for 100 hours is B L , (B H ⁇ A 0 ) / A 0 ⁇ 100 (%) ⁇ ⁇ 27 (%), and (B L ⁇ A 0 ) / A 0 ⁇ 100 (%) ⁇ ⁇ 15 (%) Satisfy at least one of the following.
- the test that is allowed to stand at a temperature of 200 ° C. for 24 hours is referred to as a heat resistance test
- the test that is irradiated with a 250 W strength xenon lamp for 100 hours is referred to as a light resistance test
- (B H ⁇ A 0 ) / A 0 ⁇ 100 (%) is a heat resistance test.
- the post contact angle change rate D H , (B L ⁇ A 0 ) / A 0 ⁇ 100 (%) will be described as the contact angle change rate D L after the light resistance test.
- the contact angle means a value measured by the ⁇ / 2 method using 3 ⁇ L of water.
- the initial contact angle A 0 means the contact angle of a transparent film that has not been subjected to a heat resistance test or a light resistance test.
- the contact angle change rate DH after the heat test is ⁇ 27 (%) or more, preferably ⁇ 27.0 (%) or more, more preferably ⁇ 18 (%) or more, and even more preferably. Is -10 (%) or more, more preferably -5 (%) or more, and usually preferably 10 (%) or less.
- the contact angle change rate DH after the heat test is within this range, both water and oil repellency and weather resistance can be achieved.
- Light resistance test After contact angle change rate D L is -15% or more, preferably -15.0 (%) or more, more preferably -8% or higher, even more preferably -3 ( %) Or more, and usually preferably 10 (%) or less. If after a light resistance test contact angle change rate D L is in this range, it is possible to achieve both the water and oil repellency, and weather resistance.
- the initial contact angle A 0 is preferably at least 80 °, more preferably at least 90 °, even more preferably at least 95 °, even more preferably at least 98 °, particularly preferably at least 100 °, usually at 180 °. It is preferable that the angle is not more than °.
- the contact angle B H after the heat test is preferably 75 ° or more, more preferably 85 ° or more, still more preferably 90 ° or more, and usually preferably 180 ° or less.
- the contact angle BL after the light resistance test is preferably 75 ° or more, more preferably 90 ° or more, still more preferably 95 ° or more, and usually preferably 180 ° or less.
- the transparent film of the present invention is a transparent film comprising a polysiloxane skeleton and a trialkylsilyl group-containing molecular chain bonded to a part of silicon atoms among silicon atoms forming the polysiloxane skeleton.
- the alkyl group in the alkylsilyl group-containing molecular chain may be replaced by a fluoroalkyl group, and the transparent film of the present invention has an initial contact angle of droplets on the transparent film of A 1 (wavelength) region of 300 nm or less.
- the contact angle change rate ((B z1 ⁇ A 1 ) / A 1 ⁇ 100 (%)) preferably satisfies the relationship represented by the following formula. (B z1 ⁇ A 1 ) / A 1 ⁇ 100 (%) ⁇ ⁇ 9 (%)
- the transparent film of the present invention has particularly good light resistance, and even when irradiated with high-intensity light, the water and oil repellency properties are unlikely to deteriorate.
- the contact angle change rate ((B z1 ⁇ A 1 ) / A 1 ⁇ 100 (%)) before and after the 4-hour irradiation is preferably ⁇ 9.0 (%) or more, more preferably ⁇ 7% or more. More preferably, it is -5% or more, particularly preferably -3% or more.
- the transparent film of the present invention is in contact with droplets on the transparent film after irradiation with a mercury lamp having an emission line in the (wavelength) region of 300 nm or less for 6 hours at an irradiation surface intensity of 200 ⁇ 10 mW / cm 2.
- the contact angle change rate ((B z2 ⁇ A 1 ) / A 1 ⁇ 100 (%)) preferably satisfies the relationship represented by the following formula.
- the contact angle change rate ((B z2 ⁇ A 1 ) / A 1 ⁇ 100 (%)) before and after the 6-hour irradiation is more preferably ⁇ 16% or more, further preferably ⁇ 10% or more, and still more preferably ⁇ It is 7% or more, particularly preferably -5% or more, and may be, for example, -1% or less.
- the irradiation with the mercury lamp is preferably performed in an air atmosphere, the temperature is preferably 20 ° C. or more and 40 ° C. or less, and the humidity is preferably 30% or more and 75% or less.
- Examples of mercury lamps having a bright line in the (wavelength) region of 300 nm or less include “SP-9 250DB” manufactured by USHIO INC. And equivalents thereof.
- the thickness of the transparent film of the present invention is, for example, 0.2 to 2000 nm, preferably 0.5 to 1000 nm, more preferably 1 to 80 nm. Also, it may be 200 nm or less, 100 nm or less, and 40 nm or less is allowed.
- the transparent film of the present invention preferably has a total light transmittance in accordance with JIS K 7361-1 or JIS K 7375 of 70% or more, more preferably 80% or more, and 85% or more. Is more preferable.
- the transparent film is composed of a polysiloxane skeleton, and some of the silicon atoms forming the polysiloxane skeleton A trialkylsilyl group-containing molecular chain may be bonded to the.
- the alkyl group in the trialkylsilyl group-containing molecular chain may be replaced with a fluoroalkyl group.
- the polysiloxane skeleton means a skeleton in which silicon atoms and oxygen atoms are alternately arranged and silicon atoms are three-dimensionally connected through oxygen atoms.
- the polysiloxane skeleton desirably has a three-dimensional network structure with Si—O—Si bonds, but may have a structure in which a divalent hydrocarbon group intervenes between silicon atoms if necessary.
- the transparent film of the present invention has a structure (A) in which a trialkylsilyl group-containing molecular chain is bonded to some silicon atoms among silicon atoms forming a polysiloxane skeleton.
- a trialkylsilyl group-containing molecular chain is a monovalent group having a molecular chain to which a trialkylsilyl group is bonded.
- the trialkylsilyl group is bonded to the molecular chain, so that the surface of the transparent film is repelled (surface).
- Improves water and oil repellency improves water and oil repellency.
- the presence of a trialkylsilyl group-containing molecular chain reduces friction between the droplet (water droplet, oil droplet, etc.) and the transparent film, and facilitates movement of the droplet.
- chemical and physical durability are enhanced, and heat resistance and light resistance are improved.
- the alkyl group of the trialkylsilyl group is replaced with a fluoroalkyl group, the water / oil repellency of the transparent film interface (surface) can be improved.
- the number of carbon atoms in the alkyl group contained in the trialkylsilyl group is preferably 1 or more and 4 or less, more preferably 1 or more and 3 or less, and still more preferably 1 or more and 2 or less. Moreover, it is preferable that the total carbon number of the three alkyl groups contained in a trialkylsilyl group is 9 or less, More preferably, it is 6 or less, More preferably, it is 4 or less.
- Specific examples of the alkyl group contained in the trialkylsilyl group include a methyl group, an ethyl group, a propyl group, and a butyl group.
- the three alkyl groups in the trialkylsilyl group may be the same or different from each other, but are preferably the same. Further, the trialkylsilyl group preferably contains at least one methyl group, more preferably 2 or more, and particularly preferably all three alkyl groups are methyl groups.
- trialkylsilyl group examples include a methyldiethylsilyl group, a methylethylpropylsilyl group, a methylethylbutylsilyl group, a methyldipropylsilyl group, a methylpropylbutylsilyl group, and a methyldibutylsilyl group.
- a trialkylsilyl group in which a group is bonded to a silicon atom a trialkylsilyl group in which two methyl groups such as a dimethylethylsilyl group, a dimethylpropylsilyl group, and a dimethylbutylsilyl group are bonded to a silicon atom; a trimethylsilyl group; Etc.
- the whole or part of the alkyl group contained in the trialkylsilyl group may be replaced with a trialkylsilyloxy group. Even in such a case, the trialkylsilyl group-containing molecular chain has a trialkylsilyl group.
- the trialkylsilyloxy group to be substituted include a group in which an oxygen atom is bonded to the silicon atom of the trialkylsilyl group selected from the range described above, and one or more methyl groups are bonded to the silicon atom.
- a trialkylsilyloxy group is preferable, a trialkylsilyloxy group in which two or more methyl groups are bonded to a silicon atom is more preferable, and a trialkylsilyloxy group in which three methyl groups are bonded to a silicon atom is particularly preferable.
- the number of trialkylsilyl groups contained in the trialkylsilyl group-containing molecular chain is preferably 2 or more, more preferably 3 in some cases.
- alkyl group of the trialkylsilyl group and the alkyl group of the trialkylsilyloxy group that may replace the alkyl group contained in the trialkylsilyl group may be entirely replaced with a fluoroalkyl group.
- a fluoroalkyl group include groups in which at least a part of the hydrogen atoms of the alkyl group are substituted with fluorine atoms.
- the number of carbon atoms is preferably 1 or more and 4 or less, more preferably 1 or more. 3 or less, more preferably 1 or more and 2 or less.
- the number of substitution of fluorine atoms is preferably 1 or more, for example, when the number of carbon atoms is A, and is preferably 2 ⁇ A + 1 or less.
- the fluoroalkyl group include a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group (perfluoromethyl group), a monofluoroethyl group, a difluoroethyl group, a trifluoroethyl group, a tetrafluoroethyl group, Pentafluoroethyl group (perfluoroethyl group), monofluoropropyl group, difluoropropyl group, trifluoropropyl group, tetrafluoropropyl group, pentafluoropropyl group, hexafluoropropyl group, heptafluoropropyl group (perfluoropropyl group) , Monofluoromethyl group
- the number of substitutions can be appropriately selected within the range of 1 to 3 per silicon atom.
- the trialkylsilyl group is preferably bonded to the end of the molecular chain (free end side), particularly the main chain end (free end side).
- the water and oil repellency of the transparent film is improved, and the heat resistance and light resistance are improved.
- the molecular chain to which the trialkylsilyl group is bonded is preferably linear or branched, and is preferably linear.
- the molecular chain is preferably a dialkylsiloxane chain, and is preferably a linear dialkylsiloxane chain.
- the dialkylsiloxane chain means a molecular chain in which silicon atoms to which two alkyl groups are bonded and oxygen atoms are alternately connected.
- the alkyl group bonded to the silicon atom of the dialkylsiloxane chain preferably has 1 to 4 carbon atoms, more preferably 1 to 3 carbon atoms, and still more preferably 1 to 2 carbon atoms.
- Specific examples of the alkyl group bonded to the silicon atom of the dialkylsiloxane chain include a methyl group, an ethyl group, a propyl group, and a butyl group.
- dialkylsiloxane chain examples include a (poly) dimethylsiloxane chain and a (poly) diethylsiloxane chain.
- the number of repeating dialkylsilyloxy groups is 1 or more, preferably 100 or less, more preferably 80 or less, still more preferably 50 or less, particularly preferably 20 or less, most preferably. 15 or less.
- a plurality of the dialkylsiloxane chains may be connected in series.
- a divalent hydrocarbon group may be included in a part of this series structure. Specifically, some oxygen atoms in the dialkylsiloxane chain may be replaced with a divalent hydrocarbon group. In this way, even if a part of the group is replaced with a hydrocarbon group, the remainder is a dialkylsiloxane chain, so that a transparent film having high chemical and physical durability and excellent heat resistance and light resistance is obtained.
- the divalent hydrocarbon group preferably has 10 or less carbon atoms, more preferably 6 or less carbon atoms, still more preferably 4 or less carbon atoms, and usually preferably 1 or more carbon atoms.
- the divalent hydrocarbon group is preferably chain-like, and when it is chain-like, it may be either linear or branched.
- the divalent hydrocarbon group is preferably a divalent aliphatic hydrocarbon group, and is preferably a divalent saturated aliphatic hydrocarbon group.
- Specific examples of the divalent hydrocarbon group include divalent saturated aliphatic hydrocarbon groups such as a methylene group, an ethylene group, a propylene group, and a butylene group.
- the divalent hydrocarbon group contained in the dialkylsiloxane chain may be a group in which a part of the methylene group (—CH 2 —) of the hydrocarbon group is replaced with an oxygen atom, if necessary. It is preferable that two consecutive methylene groups (—CH 2 —) are not replaced with oxygen atoms at the same time, and a methylene group (—CH 2 —) adjacent to the Si atom is not replaced with oxygen atoms.
- Specific examples of the group in which a part of the hydrocarbon group is replaced with an oxygen atom include a group having a (poly) ethylene glycol unit, a group having a (poly) propylene glycol unit, and the like.
- the dialkylsiloxane chain is preferably composed only of repeating dialkylsilyloxy groups.
- the dialkylsiloxane chain consists only of repeating dialkylsilyloxy groups, the light resistance of the transparent film becomes even better.
- Examples of the molecular chain contained in the trialkylsilyl group-containing molecular chain include a molecular chain represented by the following formula.
- * on the right side represents a bond bonded to the silicon atom forming the polysiloxane skeleton
- * on the left side represents a bond bonded to the trialkylsilyl group.
- the number of elements constituting the trialkylsilyl group-containing molecular chain is preferably 24 or more, more preferably 40 or more, still more preferably 50 or more, and preferably 1200 or less, more preferably 700 or less, more preferably 250 or less.
- the trialkylsilyl group-containing molecular chain is preferably represented by the following formula (s1).
- R s1 each independently represents a hydrocarbon group or a trialkylsilyloxy group. However, when all of R s1 are hydrocarbon groups, these hydrocarbon groups are alkyl groups.
- R s2 represents a dialkylsiloxane chain, and the oxygen atom of the dialkylsiloxane chain may be replaced with a divalent hydrocarbon group, and a methylene group (—CH 2 —) as a part of the divalent hydrocarbon group. May be replaced by an oxygen atom.
- * Represents a bond with a silicon atom.
- the hydrocarbon group represented by R s1 preferably has 1 to 4 carbon atoms, more preferably 1 to 3 carbon atoms, and still more preferably 1 to 2 carbon atoms. .
- the hydrocarbon group for R s1 may be either linear or branched, but is preferably linear.
- the hydrocarbon group for R s1 is preferably an aliphatic hydrocarbon group, and more preferably an alkyl group. Specific examples of the hydrocarbon group for R s1 include linear saturated aliphatic hydrocarbon groups such as a methyl group, an ethyl group, a propyl group, and a butyl group.
- the trialkylsilyloxy group for R s1 can be appropriately selected from the above-described range. Furthermore, when all of the plurality of R s1 are hydrocarbon groups, R s1 is preferably an alkyl group. Dialkyl siloxane chain of R s2 and, dialkyl siloxane chain hydrocarbon radical oxygen atom divalent may be replaced in the R s2 is appropriately selected from the range described above.
- the trialkylsilyl group-containing molecular chain is more preferably a group represented by the following formula (s1-1), more preferably a group represented by the following formula (s1-1-1). .
- each R s3 independently represents an alkyl group having 1 to 4 carbon atoms.
- R s4 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, and the methylene group (—CH 2 —) in R s4 may be replaced with an oxygen atom.
- R s5 independently represents an alkyl group having 1 to 4 carbon atoms.
- m1 and n1 each independently represents an integer of 0 or more. * Represents a bond with a silicon atom. However, the order of existence of each repeating unit with subscripts n1 and m1 and enclosed in parentheses is arbitrary in the formula. ]
- R s3 , R s5 and n1 have the same meanings as above. * Represents a bond with a silicon atom. ]
- the trialkylsilyl group-containing molecular chain is preferably a group represented by the following formula (s1-2), and among the groups represented by the formula (s1-2), the following formula (s1-2) The group represented by 1) is more preferable.
- R s8 independently represents an alkyl group having 1 to 4 carbon atoms.
- R s9 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, and the methylene group (—CH 2 —) in R s9 may be replaced with an oxygen atom.
- R s10 independently represents an alkyl group having 1 to 4 carbon atoms.
- m2 and n2 each independently represents an integer of 0 or more. * Represents a bond with a silicon atom. However, the order of presence of each repeating unit with subscripts n2 and m2 enclosed in parentheses is arbitrary in the formula. ]
- R s8 , R s10 and n2 have the same meanings as above. * Represents a bond with a silicon atom. ]
- the alkyl group of R s3 and R s8 has 1 to 3 carbon atoms. Is preferable, more preferably 1 or more and 2 or less, and particularly preferably 1 carbon. Specific examples of the alkyl group for R s3 include a methyl group, an ethyl group, and a propyl group.
- the divalent hydrocarbon group of R s4 and R s9 can be appropriately selected from the above-described range as a hydrocarbon group that may replace the oxygen atom of the dialkylsiloxane chain, and is a linear or branched chain having 1 to 4 carbon atoms A divalent saturated aliphatic hydrocarbon group is preferred.
- the alkyl group of R s5 and R s10 can be appropriately selected from the ranges described above as the alkyl group of the trialkylsilyl group, and is an alkyl group contained in * -Si (R s5 ) 3 or * -Si (R s10 ) 3
- the number of carbon atoms is preferably 1 or more and 4 or less, more preferably 1 or more and 3 or less, and still more preferably 1 or more and 2 or less.
- the total carbon number of the three alkyl groups contained in a trialkylsilyl group is 9 or less, More preferably, it is 6 or less, More preferably, it is 4 or less.
- * -Si (R s5 ) 3 preferably contains at least one methyl group, more preferably two or more, and particularly preferably all three alkyl groups are methyl groups.
- . m1 and m2 are preferably 0 or more and 4 or less, and more preferably 0 or more and 3 or less.
- N1 and n2 are preferably 1 or more and 100 or less, more preferably 1 or more and 80 or less, still more preferably 1 or more and 50 or less, particularly preferably 1 or more and 30 or less, and most preferably 1 or more. , 20 or less.
- each repeating unit with subscripts n1 and m1 and enclosed in parentheses is arbitrary in the formula.
- the order of existence of each repeating unit with parentheses n1, m1 and parentheses, and the order of existence of each repeating unit with parentheses n2, m2 are as described in the formula. It may be the order.
- trialkylsilyl group-containing molecular chain examples include groups represented by the following formulae.
- the silicon atom to which the trialkylsilyl group-containing molecular chain is bonded is bonded with two —O— groups for siloxane bonding, and the remaining one group is a molecular chain of the trialkylsilyl group-containing molecular chain.
- a group containing a hydrocarbon chain having a carbon number smaller than the number of elements constituting the molecular chain of the siloxane skeleton-containing group or the trialkylsilyl group-containing molecular chain having a number of elements smaller than the number of elements constituting the group (hereinafter referred to as “hydrocarbon” May be referred to as a “chain-containing group”).
- the siloxane skeleton-containing group only needs to contain a siloxane unit (Si—O—) and be composed of a smaller number of elements than the number of elements constituting the molecular chain of the trialkylsilyl group-containing molecular chain.
- the siloxane skeleton-containing group is a group having a shorter length than the trialkylsilyl group-containing molecular chain or a small steric spread (bulk height).
- the siloxane skeleton-containing group is preferably a chain, and when it is a chain, it may be linear or branched.
- the siloxane unit (Si—O—) is preferably a dialkylsilyloxy group. Examples of the dialkylsilyloxy group include a dimethylsilyloxy group and a diethylsilyloxy group.
- the number of repeating siloxane units (Si—O—) is preferably 1 or more, preferably 5 or less, more preferably 3 or less.
- the siloxane skeleton-containing group may contain a divalent hydrocarbon group in a part of the siloxane skeleton.
- a part of oxygen atoms in the siloxane skeleton may be replaced with a divalent hydrocarbon group.
- the divalent hydrocarbon group that may replace some oxygen atoms of the siloxane skeleton the divalent hydrocarbon that may replace oxygen atoms of the dialkylsiloxane chain contained in the trialkylsilyl group-containing molecular chain
- a group similar to the group can be preferably exemplified.
- the terminal (free end) silicon atom of the siloxane skeleton-containing group is a hydrocarbon group (preferably an alkyl group) in addition to an —O— group for forming a siloxane unit (Si—O—) with an adjacent silicon atom or the like. Group), a hydroxy group and the like.
- the siloxane skeleton-containing group has a trialkylsilyl group, but can function as a spacer if the number of elements is smaller than the coexisting trialkylsilyl group-containing molecular chain. Even when the siloxane skeleton-containing group includes a trialkylsilyl group, the alkyl group of the trialkylsilyl group may be replaced with a fluoroalkyl group.
- the number of elements in the siloxane skeleton-containing group is preferably 100 or less, more preferably 50 or less, still more preferably 30 or less, and usually 10 or more.
- the difference in the number of elements between the trialkylsilyl group-containing molecular chain and the siloxane skeleton-containing group is preferably 10 or more, more preferably 20 or more, and usually preferably 1000 or less, more preferably 500. Hereinafter, it is more preferably 200 or less.
- the siloxane skeleton-containing group is preferably, for example, a group represented by the following formula (s2).
- R s6 each independently represents a hydrocarbon group or a hydroxy group.
- R s7 independently represents an alkyl group having 1 to 4 carbon atoms.
- q represents an integer of 0 or more and 4 or less. * Represents a bond with a silicon atom.
- examples of the hydrocarbon group for R s6 include the same groups as the groups exemplified as the hydrocarbon group for R s1 , preferably an aliphatic hydrocarbon group, and preferably a methyl group or an ethyl group It is more preferably a linear saturated aliphatic hydrocarbon group such as propyl group or butyl group.
- R s6 is preferably a hydrocarbon group.
- the methylene group contained in the hydrocarbon group of R s6 may be replaced with an oxygen atom.
- examples of the alkyl group having 1 to 4 carbon atoms of R s7 include the same groups as those described for R s3 in the formula (s1-1).
- siloxane skeleton-containing group examples include groups represented by the following formulas.
- the hydrocarbon chain-containing group may be any group having a hydrocarbon chain portion having fewer carbon atoms than the number of elements constituting the molecular chain of the trialkylsilyl group-containing molecular chain.
- the number of carbon atoms of the longest straight chain of the hydrocarbon chain is preferably smaller than the number of elements constituting the longest straight chain of the trialkylsilyl group-containing molecular chain.
- the hydrocarbon chain-containing group is usually composed only of a hydrocarbon group (hydrocarbon chain), but if necessary, a group in which a part of the methylene group (—CH 2 —) of the hydrocarbon chain is replaced with an oxygen atom. It may be.
- the methylene group (—CH 2 —) adjacent to the Si atom is not replaced with an oxygen atom, and two consecutive methylene groups (—CH 2 —) are not replaced with an oxygen atom at the same time.
- the carbon number of the hydrocarbon chain portion means the number of carbon atoms constituting the hydrocarbon group (hydrocarbon chain) in the oxygen non-substituted hydrocarbon chain-containing group, and includes the oxygen-substituted hydrocarbon chain. In the group, the number of carbon atoms is assumed assuming that the oxygen atom is a methylene group (—CH 2 —).
- hydrocarbon chain-containing group will be described by taking an oxygen-nonsubstituted hydrocarbon chain-containing group (that is, a monovalent hydrocarbon group) as an example.
- an oxygen-nonsubstituted hydrocarbon chain-containing group that is, a monovalent hydrocarbon group
- the methylene group — Part of CH 2 —
- oxygen atoms can be replaced with oxygen atoms.
- the number of carbon atoms is preferably 1 or more and 3 or less, more preferably 1.
- the hydrocarbon chain-containing group (in the case of a hydrocarbon group) may be branched or linear.
- the hydrocarbon chain-containing group in the case of a hydrocarbon group is preferably a saturated or unsaturated aliphatic hydrocarbon chain-containing group, and more preferably a saturated aliphatic hydrocarbon chain-containing group.
- the saturated aliphatic hydrocarbon chain-containing group is more preferably a saturated aliphatic hydrocarbon group. Examples of the saturated aliphatic hydrocarbon group include a methyl group, an ethyl group, and a propyl group.
- the structure (A) in which the trialkylsilyl group-containing molecular chain is bonded to the silicon atom forming the polysiloxane skeleton is preferably, for example, represented by the following formula (1).
- R a represents a trialkylsilyl group-containing molecular chain
- Z a1 represents a trialkylsilyl group-containing molecular chain, a siloxane skeleton-containing group, a hydrocarbon chain-containing group, or an —O— group.
- Z a1 is a trialkylsilyl group-containing molecular chain
- R a and Z a1 may be the same or different.
- R a and Z a1 may be the same or different between the plurality of formulas (1).
- R a , Z a1 trialkylsilyl group-containing molecular chain, Z a1 siloxane skeleton-containing group, and hydrocarbon chain-containing group are respectively a trialkylsilyl group-containing molecular chain, a siloxane skeleton-containing group,
- the hydrocarbon chain-containing group can be appropriately selected from the range described above.
- Z a1 is preferably a siloxane skeleton-containing group or —O— group, and more preferably —O— group.
- structures represented by the following formulas (1-1) to (1 to 32) can be preferably exemplified.
- the transparent film of the present invention has a metal atom selected from trivalent or tetravalent metal atoms capable of forming a metal alkoxide and a number of elements smaller than the number of elements constituting the molecular chain of the trialkylsilyl group-containing molecular chain.
- hydrocarbon chain-containing group or hydroxy group is bonded to a silicon atom (second silicon atom) or a metal atom different from the silicon atom to which the above-described trialkylsilyl group-containing molecular chain is bonded.
- Second silicon atoms and metal atoms also act as spacers due to the bonding of hydrocarbon chain-containing groups or hydroxy groups with a small number of carbon atoms, and the water / oil repellency improvement effect of trialkylsilyl group-containing molecular chains Can be increased.
- the group bonded to the metal atom is preferably a siloxane skeleton-containing group or a hydroxy group.
- R b1 represents a siloxane skeleton-containing group, a hydrocarbon chain-containing group, a hydroxy group or an —O— group
- Z b1 represents a siloxane skeleton-containing group, a hydrocarbon chain-containing group, a hydroxy group, Or a —O— group
- Z b1 and R b1 may be the same or different
- a plurality of formulas (2 ) R b1 and Z b1 may be the same or different.
- M represents a trivalent or tetravalent metal atom capable of forming a metal alkoxide
- j1 represents an integer of 0 or 1 depending on M.
- R b10 represents a fluorocarbon-containing group.
- Z b10 represents a siloxane skeleton-containing group, a hydrocarbon chain-containing group, a hydrolyzable group, or an —O— group.
- R b10 and Z b10 may be the same or different among a plurality of formulas (2-II).
- R b11 represents a hydrolyzable silane oligomer residue
- Z b11 represents a hydrolyzable group, a fluorine-containing alkyl group having 1 to 12 carbon atoms, or an alkyl having 1 to 4 carbon atoms. Represents a group or —O— group.
- the siloxane skeleton-containing group and the hydrocarbon chain-containing group of R b1 and Z b1 can be appropriately selected from the ranges described above.
- R b1 is preferably a siloxane skeleton-containing group, a hydrocarbon chain-containing group, or a hydroxy group, more preferably a siloxane skeleton-containing group or a hydroxy group, and even more preferably a hydroxy group.
- R b1 is preferably an —O— group.
- Z b1 is preferably a siloxane skeleton-containing group, a hydroxy group or an —O— group, and more preferably a hydroxy group or an —O— group.
- M examples include trivalent metals such as B, Al, Ge, Ga, Y, In, Sb, and La; tetravalent metals such as Si, Ti, Ge, Zr, Sn, and Hf; Al, Si, Ti and Zr are preferable, and Si is particularly preferable.
- trivalent metals such as B, Al, Ge, Ga, Y, In, Sb, and La
- tetravalent metals such as Si, Ti, Ge, Zr, Sn, and Hf
- Al, Si, Ti and Zr are preferable, and Si is particularly preferable.
- j1 represents 0 when M is a trivalent metal, and 1 when M is a tetravalent metal.
- the fluorocarbon-containing group represented by R b10 is preferably a group having 1 to 15 carbon atoms, more preferably a group having 1 to 12 carbon atoms, A group having 8 is more preferable, and a group having 1 to 6 carbon atoms is particularly preferable. Specifically, a group having a fluoroalkyl group at the terminal is preferable, and a group having a terminal trifluoromethyl group is particularly preferable. As the fluorocarbon-containing group, a group represented by the formula (f-1) is preferable.
- R f1 each independently represents a fluorine atom or an alkyl group having 1 to 12 carbon atoms substituted with one or more fluorine atoms.
- Each R 1 independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
- L f1 independently represents —O—, —COO—, —OCO—, —NR—, —NRCO—, —CONR— (R represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a carbon number) 1 to 4 fluorine-containing alkyl groups).
- h1 to h5 are each independently an integer of 0 to 100, and the total value of h1 to h5 is 100 or less. Further, the order of each repeating unit attached with h1 to h5 and enclosed in parentheses is arbitrary in the formula. * Represents a bond with M. ]
- the repeating units containing Si are not adjacent to each other.
- R f1 is preferably a fluorine atom or a perfluoroalkyl having 1 to 10 carbon atoms (more preferably 1 to 5 carbon atoms).
- R 1 is preferably a hydrogen atom or alkyl having 1 to 4 carbon atoms.
- A is preferably —O—, —COO—, or —OCO—.
- h1 is preferably 1 or more and 30 or less, more preferably 1 or more and 25 or less, still more preferably 1 or more and 10 or less, particularly preferably 1 or more and 5 or less, and most preferably 1 or 2.
- h2 is preferably 0 or more and 15 or less, and more preferably 0 or more and 10 or less.
- h3 is preferably 0 or more and 5 or less, more preferably 0 or more and 2 or less.
- h4 is preferably 0 or more and 4 or less, more preferably 0 or more and 2 or less.
- h5 is preferably 0 or more and 4 or less, more preferably 0 or more and 2 or less.
- the total value of h1 to h5 is preferably 3 or more, more preferably 5 or more, and preferably 80 or less, more preferably 50 or less, and still more preferably 20 or less.
- R f1 is a fluorine atom or a perfluoroalkyl having 1 to 5 carbon atoms
- R 1 is a hydrogen atom
- h3, h4 and h5 are all 0, h1 is 1 or more and 5 or less, and h2 is 0. It is preferable that the number is 5.
- fluorocarbon-containing group examples include C r1 F 2r1 + 1 — (r1 is an integer of 1 to 12), CF 3 CH 2 O (CH 2 ) r2 —, CF 3 (CH 2 ) r3 Si (CH 3 ) 2 (CH 2 ) r2 —, CF 3 COO (CH 2 ) r2 — (r2 is 5 to 20, preferably 8 to 15, and r3 is 1 to 7, preferably 2 to 6 CF 3 (CF 2 ) r 4 — (CH 2 ) r 5 —, CF 3 (CF 2 ) r 4 —C 6 H 4 — (wherein r 4 is 1 to 10, preferably 3 to 7 and all of r5 are 1 to 5, preferably 2 to 4).
- fluorocarbon-containing group examples include a fluoroalkyl group, a fluoroalkyloxyalkyl group, a fluoroalkylsilylalkyl group, a fluoroalkylcarbonyloxyalkyl group, a fluoroalkylaryl group, a fluoroalkylalkenyl group, and a fluoroalkylalkynyl group. It is done.
- fluoroalkyl group examples include fluoromethyl group, fluoroethyl group, fluoropropyl group, fluorobutyl group, fluoropentyl group, fluorohexyl group, fluoroheptyl group, fluorooctyl group, fluorononyl group, fluorodecyl group, fluoro Examples thereof include a fluoroalkyl group having 1 to 12 carbon atoms such as an undecyl group and a fluorododecyl group.
- fluoroalkoxyalkyl group examples include a fluoromethoxy C 5-20 alkyl group, a fluoroethoxy C 5-20 alkyl group, a fluoropropoxy C 5-20 alkyl group, and a fluorobutoxy C 5-20 alkyl group.
- the fluoroalkyl silyl group for example, fluoromethyl silyl C 5-20 alkyl group, fluoroethyl silyl C 5-20 alkyl group, fluoropropyl silyl C 5-20 alkyl group, fluoro-butylsilyl C 5-20 alkyl group, fluoro pentylsilyl C 5-20 alkyl group, fluoro hexylsilyl C 5-20 alkyl group, Puchirushiriru to fluoro C 5-20 alkyl group, such as perfluorooctyl silyl C 5-20 alkyl group.
- fluoroalkylcarbonyloxyalkyl group examples include a fluoromethylcarbonyloxy C 5-20 alkyl group, a fluoroethylcarbonyloxy C 5-20 alkyl group, a fluoropropylcarbonyloxy C 5-20 alkyl group, and a fluorobutylcarbonyloxy C 5-20.
- An alkyl group etc. are mentioned.
- fluoroalkylaryl group include a fluoro C 1-8 alkylphenyl group and a fluoro C 1-8 alkyl naphthyl group.
- fluoroalkylalkenyl group examples include a fluoro C 1-17 alkyl vinyl group, and a fluoroalkylalkynyl group.
- Groups include fluoro C 1-17 alkylethynyl groups.
- Z b10 is preferably a siloxane skeleton-containing group, a hydroxy group or an —O— group, more preferably a hydroxy group or an —O— group.
- the number of silicon atoms contained in the hydrolyzable silane oligomer residue of R b11 is, for example, 3 or more, preferably 5 or more, more preferably 7 or more.
- the condensation number is preferably 15 or less, more preferably 13 or less, and even more preferably 10 or less.
- examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, and a butoxy group, and a methoxy group and an ethoxy group are preferable.
- the oligomer residue may have one or more of these alkoxy groups, and preferably has one.
- the hydrolyzable silane oligomer residue is preferably a group represented by the following formula (f-2).
- each X independently represents a hydrolyzable group, a fluorine-containing alkyl group having 1 to 12 carbon atoms or an alkyl group having 1 to 4 carbon atoms.
- h6 is an integer of 0 or more and 100 or less. * Represents a bond with Si.
- the hydrolyzable group of X is preferably an alkoxy group having 1 to 4 carbon atoms (preferably 1 to 2) such as a methoxy group, an ethoxy group, a propoxy group or a butoxy group; an allyl group; . h6 is preferably 0 or more and 10 or less, and more preferably 0 or more and 7 or less. It is also preferred that at least one of X is a fluorine-containing alkyl group having 1 to 12 carbon atoms (preferably 1 to 4 carbon atoms). Of X, at least one is preferably a hydrolyzable group (particularly a methoxy group, an ethoxy group, or an allyl group). X is preferably a hydrolyzable group or a fluorine-containing alkyl group having 1 to 12 carbon atoms (preferably 1 to 4 carbon atoms).
- hydrolyzable silane oligomer residue of R b11 examples include (C 2 H 5 O) 3 Si— (OSi (OC 2 H 5 ) 2 ) 4 O— *, (CH 3 O) 2 (CF 3 CH 2 CH 2 ) Si— (OSi (OCH 3 ) (CH 2 CH 2 CF 3 )) 4 —O— * and the like.
- the hydrolyzable group in Z b11 is an alkoxy group having 1 to 4 carbon atoms (preferably 1 to 2 carbon atoms) such as a methoxy group, an ethoxy group, a propoxy group, or a butoxy group.
- a hydrogen atom; a cyano group; an allyl group; and an alkoxy group is preferred.
- Z b11 is preferably a hydrolyzable group, a fluorine-containing alkyl group having 1 to 12 carbon atoms, or an —O— group.
- the number of carbon atoms of the fluorine-containing alkyl group in Zb11 is preferably 1-8, more preferably 1-4.
- the fluorine-containing alkyl group represents a group in which some or all of the hydrogen atoms contained in an alkyl group such as a methyl group, an ethyl group, a propyl group, and a butyl group are substituted with a fluorine atom, a fluoromethyl group, a fluoroethyl group Fluoroalkyl groups such as fluoropropyl group and fluorobutyl group; perfluoroalkyl groups such as perfluoromethyl group, perfluoroethyl group, perfluoropropyl group and perfluorobutyl group;
- the carbon number of the alkyl group in R b11 is preferably 1 to 3, and more preferably 1 to 2.
- Examples of the alkyl group for R b11 include a methyl group, an ethyl group, a propyl group, and a butyl group.
- the abundance ratio of the structure (B) to the structure (A) is preferably 0.1 or more, more preferably 5 or more on a molar basis. More preferably, it is 8 or more, preferably 80 or less, more preferably 60 or less, still more preferably 50 or less.
- the transparent film of the present invention has a change in contact angle before and after thermal history or before and after light irradiation within a certain range, both water and oil repellency properties, heat resistance and light resistance are compatible. Is possible.
- the trialkylsilyl group-containing molecular chain has a structure in which some silicon atoms are bonded to silicon atoms on the polysiloxane skeleton constituting the transparent film.
- the hydrolyzable groups of the organosilicon compound (a) and the metal compound (b) are hydrolyzed and polycondensed, and a trialkylsilyl group-containing molecular chain is formed on the silicon atom on the skeleton.
- a bonded siloxane skeleton is formed.
- the organosilicon compound (a) is preferably one in which at least one trialkylsilyl group-containing molecular chain and at least one hydrolyzable group are bonded to a silicon atom in one molecule.
- the number of trialkylsilyl group-containing molecular chains bonded to the central silicon atom is 1 or more, preferably 3 or less, more preferably 2 or less, and particularly preferably 1 It is.
- the hydrolyzable group may be any group that can give a hydroxy group (silanol group) by hydrolysis.
- an alkoxy group having 1 to 4 carbon atoms such as a methoxy group, an ethoxy group, a propoxy group, or a butoxy group; Preferred examples include a group; an acetoxy group; a chlorine atom; an isocyanate group; Among these, an alkoxy group having 1 to 4 carbon atoms is preferable, and an alkoxy group having 1 to 2 carbon atoms is more preferable.
- the number of hydrolyzable groups bonded to the central silicon atom is 1 or more, preferably 2 or more, and usually 3 or less.
- the central silicon atom of the organosilicon compound (a) includes a siloxane having a number of elements smaller than the number of elements constituting the molecular chain of the trialkylsilyl group-containing molecular chain, in addition to the trialkylsilyl group-containing molecular chain and hydrolyzable group.
- a hydrocarbon chain-containing group containing a hydrocarbon chain having a carbon number smaller than the number of elements constituting the molecular chain of the skeleton-containing group or the trialkylsilyl group-containing molecular chain may be bonded.
- the silicon compound (a) is preferably a compound represented by the following formula (I).
- R a represents a trialkylsilyl group-containing molecular chain, and a plurality of A a1 each independently represents a hydrolyzable group.
- Z a2 represents a trialkylsilyl group-containing molecular chain, a hydrocarbon chain-containing group, a siloxane skeleton-containing group or a hydrolyzable group.
- Z a2 and A a1 are the same It may or may not be.
- R a and Z a2 may be the same or different among a plurality of formulas (I). ]
- R a Z a2 trialkylsilyl group-containing molecular chain, Z a2 hydrocarbon chain-containing group, Z a2 siloxane skeleton-containing group, A a1 and Z a2 hydrolyzable groups are respectively , Trialkylsilyl group-containing molecular chain, hydrocarbon chain-containing group, siloxane skeleton-containing group, and hydrolyzable group can be appropriately selected from the ranges described above.
- Z a2 is preferably a siloxane skeleton-containing group or a hydrolyzable group, and more preferably a hydrolyzable group.
- Z a2 and A a1 are preferably the same group.
- the organosilicon compound (a) is preferably a compound represented by the following formula (II).
- a a1 each independently represents a hydrolyzable group.
- Z a2 represents a trialkylsilyl group-containing molecular chain, a hydrocarbon chain-containing group, a siloxane skeleton-containing group or a hydrolyzable group, and when Z a2 is a hydrolyzable group, A a1 and Z a2 are the same or different.
- R a and Z a2 may be the same or different between the formulas (II).
- R s3 each independently represents an alkyl group having 1 to 4 carbon atoms.
- R s4 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, and the methylene group (—CH 2 —) in R s4 may be replaced with an oxygen atom.
- R s5 independently represents an alkyl group having 1 to 4 carbon atoms.
- m1 and n1 each independently represents an integer of 0 or more. However, the order of existence of each repeating unit with subscripts n1 and m1 and enclosed in parentheses is arbitrary in the formula. ]
- the organosilicon compound (a) is more preferably a compound represented by the following formula (II-1).
- a a1 , Z a2 , R s3 , R s5 , and n1 are as defined above.
- organosilicon compound (a) may be a compound represented by the following formula (I-II).
- a a1 independently represents a hydrolyzable group.
- Z a2 represents a trialkylsilyl group-containing molecular chain, a hydrocarbon chain-containing group, a siloxane skeleton-containing group or a hydrolyzable group.
- Z a2 and A a1 are the same It may or may not be.
- R a and Z a2 may be the same or different among a plurality of formulas (I-II).
- R s8 independently represents an alkyl group having 1 to 4 carbon atoms.
- R s9 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, and the methylene group (—CH 2 —) in R s9 may be replaced with an oxygen atom.
- R s10 independently represents an alkyl group having 1 to 4 carbon atoms.
- m2 and n2 each independently represents an integer of 0 or more. However, the order of presence of each repeating unit with subscripts n2 and m2 enclosed in parentheses is arbitrary in the formula. ]
- each repeating unit with parentheses n1, m1 and parentheses are as described in the formula. It may be the order.
- organosilicon compound (a) a compound having one trialkylsilyl group-containing molecular chain and three hydrolyzable groups; one trialkylsilyl group-containing molecular chain, one siloxane skeleton-containing group, A compound having two hydrolyzable groups; a compound having one trialkylsilyl group-containing molecular chain, one hydrocarbon chain-containing group, and two hydrolyzable groups; and the like.
- the three hydrolyzable groups are bonded to a silicon atom.
- the group in which three hydrolyzable groups are bonded to a silicon atom include trialkoxysilyl groups such as a trimethoxysilyl group, a triethoxysilyl group, a tripropoxysilyl group, and a tributoxysilyl group; a trihydroxysilyl group; Acetoxysilyl group; trichlorosilyl group; triisocyanatesilyl group; and the like, and a compound in which one trialkylsilyl group-containing molecular chain selected from the above-described range is bonded to the silicon atom of these groups.
- Examples are compounds having one trialkylsilyl group-containing molecular chain and three hydrolyzable groups.
- one siloxane skeleton-containing group and two hydrolyzable groups are bonded to a silicon atom.
- Examples of the group having one siloxane skeleton-containing group and two hydrolyzable groups bonded to a silicon atom include trimethylsilyloxydimethoxysilyl group, trimethylsilyloxydiethoxysilyl group, trimethylsilyloxydipropoxysilyl group, and the like. And the like.
- a compound in which one trialkylsilyl group-containing molecular chain selected from the above-described range is bonded to a silicon atom at the terminal of these groups is one trialkylsilyl group.
- examples thereof include a compound having a containing molecular chain, one siloxane skeleton-containing group, and two hydrolyzable groups.
- one hydrocarbon chain-containing group and two hydrolyzable groups are silicon Bonded to an atom.
- the group in which one hydrocarbon chain-containing group and two hydrolyzable groups are bonded to a silicon atom include methyldimethoxysilyl group, ethyldimethoxysilyl group, methyldiethoxysilyl group, ethyldiethoxysilyl group, methyl group An alkyl dialkoxysilyl group such as a dipropoxysilyl group; and the like, and a compound in which one trialkylsilyl group-containing molecular chain selected from the above-described range is bonded to the silicon atom of these groups, Examples thereof include a compound having one trialkylsilyl group-containing molecular chain, one hydrocarbon chain-containing group, and two hydrolyzable groups.
- Examples of the method for synthesizing the organosilicon compound (a) include the following methods.
- a compound in which a trialkylsilyl group-containing molecular chain and a halogen atom (preferably a chlorine atom) are bonded, and a compound in which three or more (especially four) hydrolyzable groups are bonded to a silicon atom It can manufacture by making this react.
- organosilicon compound (a) all the alkyl groups of the trialkylsilyl group are replaced with trialkylsilyl groups, and these groups bonded to the dialkylsiloxane chain (the above formula (s1-1)
- a compound having a group in which m is 0) as a molecular chain containing a trialkylsilyl group is preferable, and this compound is a novel compound.
- a compound in which halogen atoms are bonded to both ends of a dialkylsiloxane chain (hereinafter, “dihalogenated dialkylsiloxane”), a tris (trialkylsilyloxy) silyl group, an M 1 O— group ( M 1 represents an alkali metal) and can be produced by reacting a compound (hereinafter referred to as “alkali metal silyl oxide”) and a compound having four hydrolyzable groups bonded to a silicon atom.
- reaction order of these compounds is not limited, it is preferable to first react a dihalogenated dialkylsiloxane and an alkali metal silyl oxide, and then react a compound having four hydrolyzable groups bonded to a silicon atom.
- a halogen atom a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. are mentioned, A chlorine atom is preferable.
- the alkali metal is preferably lithium.
- the alkali metal silyl oxide can be produced, for example, by reacting an alkyl alkali metal with a compound in which a tris (trialkylsilyloxy) silyl group and a hydroxy group are bonded.
- the organic alkali metal compound include alkyllithiums such as n-butyllithium, sec-butyllithium and tert-butyllithium, with n-butyllithium being particularly preferred.
- an organosilicon compound is reacted with, for example, alkali metal silyloxide and cyclic dimethylsiloxane, and then the silicon atom has 3 hydrolyzable groups and 1 halogen atom (especially chlorine atom). It can also be produced by reacting two bonded compounds.
- the number of silicon atoms contained in the cyclic dimethylsiloxane is, for example, preferably 2 or more and 10 or less, more preferably 2 or more and 5 or less, and further preferably 2 or more and 4 or less.
- the siloxane skeleton-containing group or the hydrocarbon chain-containing group is bonded to the metal atom.
- the number of elements of the siloxane skeleton-containing group and the number of carbon atoms of the hydrocarbon chain portion of the hydrocarbon chain-containing group are each a molecule of a trialkylsilyl group-containing molecular chain bonded to the central silicon atom of the organosilicon compound (a). Since the number of elements constituting the chain is smaller, a portion having a spacer function can be formed in the transparent film.
- a siloxane skeleton-containing group is preferable.
- the central metal atom of the metal compound (b) may be any metal atom that can be bonded to an alkoxy group to form a metal alkoxide.
- the metal includes a semimetal such as Si or Ge.
- Specific examples of the central metal atom of the metal compound (b) include trivalent metals such as Al, Fe, and In; tetravalent metals such as Hf, Si, Ti, Sn, and Zr; pentavalent metals such as Ta; Trivalent metals and tetravalent metals are preferred, more preferably trivalent metals such as Al, Fe and In; tetravalent metals such as Hf, Si, Ti, Sn and Zr; Al, Si, Ti, and Zr are preferable, and Si is particularly preferable.
- hydrolyzable group of the metal compound (b) examples include those similar to the hydrolyzable group of the organosilicon compound (a), preferably an alkoxy group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 2 carbon atoms. Groups are more preferred.
- the hydrolyzable groups of the organosilicon compound (a) and the metal compound (b) may be the same or different, but are preferably the same. Further, the hydrolyzable groups of the organosilicon compound (a) and the metal compound (b) are preferably alkoxy groups having 1 to 4 carbon atoms.
- the number of hydrolyzable groups is preferably 1 or more, more preferably 2 or more, still more preferably 3 or more, and preferably 4 or less.
- siloxane skeleton-containing group and the hydrocarbon chain-containing group of the metal compound (b) can be appropriately selected from the above-described ranges, and the number thereof is preferably 1 or less, particularly preferably 0.
- the metal compound (b) is preferably a compound represented by any one of the following formulas (II-1) to (II-3), and is represented by the formula (II-1). More preferably, it is a compound.
- each compound represented by any one of formulas (II-1) to (II-3) may be a hydrolysis condensate thereof.
- the hydrolysis condensate means a compound obtained by condensing all or some of the hydrolyzable groups of each of the compounds (II-1) to (II-3) by hydrolysis.
- M represents a trivalent or tetravalent metal atom capable of forming a metal alkoxide.
- R b2 represents a siloxane skeleton-containing group, a hydrocarbon chain-containing group, or a hydrolyzable group, and the plurality of A b1 each independently represents a hydrolyzable group.
- Z b2 represents a siloxane skeleton-containing group, a hydrocarbon chain-containing group or a hydrolyzable group.
- R b2 and A b1 may be the same or different.
- R b2 and Z b2 may be the same or different among a plurality of formulas (II-1).
- k represents an integer of 0 or 1 depending on M.
- R b10 represents a fluorocarbon-containing group having 1 to 8 carbon atoms.
- a b1 independently represents a hydrolyzable group.
- Z b10 represents a siloxane skeleton-containing group, a hydrocarbon chain-containing group, or a hydrolyzable group, and R b10 and Z b10 may be the same or different among a plurality of formulas (II-2). ]
- R b11 represents a hydrolyzable silane oligomer residue.
- X independently represents a hydrolyzable group, a fluorine-containing alkyl group having 1 to 12 carbon atoms, or an alkyl group having 1 to 4 carbon atoms.
- R b2 and Z b2 siloxane skeleton-containing groups, hydrocarbon chain-containing groups, R b2 , A b1 , and Z b2 hydrolyzable groups are siloxane skeleton-containing groups and hydrocarbon chain-containing groups, respectively.
- the group and the hydrolyzable group can be appropriately selected from the ranges described above.
- the fluorocarbon-containing group of R b2 can be appropriately selected from the ranges described above as the fluorocarbon-containing group of R b1 and the hydrolyzable silane oligomer residue.
- R b2 is preferably a siloxane skeleton-containing group or a hydrolyzable group, and more preferably a hydrolyzable group.
- Z b2 is preferably a siloxane skeleton-containing group or a hydrolyzable group, and more preferably a hydrolyzable group.
- both R b2 and Z b2 are hydrolyzable groups.
- R b2 and A b1 are preferably the same hydrolyzable group
- R b2 , A b1 and Z b2 are more preferably the same hydrolyzable group.
- the hydrolyzable group of the organosilicon compound (a) and the metal compound (b) may be the same group, and it is more preferable that both are alkoxy groups having 1 to 4 carbon atoms.
- the metal M is preferably a trivalent metal such as Al; a tetravalent metal such as Si, Ti, Zr, or Sn; more preferably Si, Al, Ti, or Zr, and particularly Si. preferable.
- a trivalent metal such as Al
- a tetravalent metal such as Si, Ti, Zr, or Sn
- Si, Al, Ti, or Zr, and particularly Si preferable.
- the proportion of other metal compounds other than the compound represented by any one of the above formulas (II-1) to (II-3) and the hydrolysis condensate thereof is 10% by mass.
- % Is preferably 5% by mass or less, more preferably 2% by mass or less, and particularly preferably 1% by mass or less.
- a compound having only a hydrolyzable group a compound having a siloxane skeleton-containing group and a hydrolyzable group; a compound having two siloxane skeleton-containing groups and a hydrolyzable group; containing a hydrocarbon chain
- a compound having two groups and a hydrolyzable group a compound having two hydrocarbon chain-containing groups and a hydrolyzable group; a compound in which a fluorocarbon-containing group and a hydrolyzable group are bonded to a silicon atom; Oligomers; and the like.
- Examples of the compound having only a hydrolyzable group include tetraalkoxysilanes such as tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, and tetrabutoxysilane; trialkoxyaluminums such as triethoxyaluminum, tripropoxyaluminum, and tributoxyaluminum; triethoxy Trialkoxy iron such as iron; trialkoxy indium such as trimethoxy indium, triethoxy indium, tripropoxy indium, tributoxy indium; tetraalkoxy hafnium such as tetramethoxy hafnium, tetraethoxy hafnium, tetrapropoxy hafnium, tetrabutoxy hafnium; tetra; Tetraal such as methoxy titanium, tetraethoxy titanium, tetrapropoxy titanium, tetrabutoxy titanium Tetraal
- Examples of the compound having a siloxane skeleton-containing group and a hydrolyzable group include trimethylsilyloxytrialkoxysilane such as trimethylsilyloxytrimethoxysilane, trimethylsilyloxytriethoxysilane, and trimethylsilyloxytripropoxysilane.
- Examples of the compound having two siloxane skeleton-containing groups and hydrolyzable groups include di (trimethylsilyloxy) such as di (trimethylsilyloxy) dimethoxysilane, di (trimethylsilyloxy) diethoxysilane, and di (trimethylsilyloxy) dipropoxysilane. Dialkoxysilane; and the like.
- Examples of the compound having a hydrocarbon chain-containing group and a hydrolyzable group include alkyltrialkoxysilanes such as methyltrimethoxysilane, ethyltrimethoxysilane, methyltriethoxysilane, ethyltriethoxysilane, and methyltripropoxysilane; vinyltrimethoxy Alkenyl trialkoxysilanes such as silane and vinyltriethoxysilane; Examples of the compound having two hydrocarbon chain-containing groups and a hydrolyzable group include dialkyl dialkoxysilanes such as dimethyldimethoxysilane, diethyldimethoxysilane, dimethyldiethoxysilane, and diethyldiethoxysilane.
- Examples of the compound in which a fluorocarbon-containing group and a hydrolyzable group are bonded to a silicon atom include CF 3 —Si— (OCH 3 ) 3 , C r1 F 2r1 + 1 —Si— (OC 2 H 5 ) 3 ( r1 is preferably an integer of 1 to 15, more preferably an integer of 1 to 12, and still more preferably an integer of 1 to 6, among which C 4 F 9 —Si— (OC 2 H 5 ) 3 , C 6 F 13 —Si— (OC 2 H 5 ) 3 , C 7 F 15 —Si— (OC 2 H 5 ) 3 , C 8 F 17 —Si— (OC 2 H 5 ) 3 are preferred.
- CF 3 CH 2 O (CH 2 ) r 2 SiCl 3 CF 3 CH 2 O (CH 2 ) r 2 Si (OCH 3 ) 3 , CF 3 CH 2 O (CH 2 ) r 2 Si (OC 2 H 5 ) 3 , CF 3 (CH 2) r3 Si (CH 3) 2 (CH 2) r2 SiCl 3, CF 3 (CH 2) r3 Si (CH 3) 2 (CH 2) r2 Si (OCH 3) 3, CF 3 ( CH 2) r3 Si (CH 3 ) 2 (CH 2) r2 Si (OC 2 H 5) 3, CF 3 COO (CH 2) r2 SiCl 3, CF 3 COO (CH 2) r2 Si (OCH 3) 3, CF 3 COO (CH 2 ) r 2 Si (OC 2 H 5 ) 3 is mentioned (all of r2 are 5 to 20, preferably 8 to 15, and r3 is 1 to 7, preferably 2 to 6).
- CF 3 (CF 2 ) r 4- (CH 2 ) r 5 SiCl 3 , CF 3 (CF 2 ) r 4- (CH 2 ) r 5 Si (OCH 3 ) 3 , CF 3 (CF 2 ) r 4- (CH 2 ) r5 Si (OC 2 H 5 ) can also be mentioned (all r4 is 1 to 10, preferably 2 to 8, more preferably 2 to 5, and r5 is all 1 to 5, preferably Is 2-4).
- CF 3 (CF 2 ) r 6 — (CH 2 ) r 7 —Si— (CH 2 CH ⁇ CH 2 ) 3 can also be mentioned (all of r6 are 2 to 10, preferably 2 to 8, and r7 Are all 1 to 5, preferably 2 to 4). Furthermore, CF 3 (CF 2) r8 - (CH 2) r9 SiCH 3 Cl 2, CF 3 (CF 2) r8 - (CH 2) r9 SiCH 3 (OCH 3) 2, CF 3 (CF 2) r8 - ( CH 2 ) r9 SiCH 3 (OC 2 H 5 ) 2 (wherein r8 is 2 to 10, preferably 3 to 7, and r9 is 1 to 5, preferably 2 to 4). Is).
- hydrolyzable silane oligomer examples include (H 5 C 2 O) 3 —Si— (OSi (OC 2 H 5 ) 2 ) 4 OC 2 H 5 , (H 3 CO) 2 —Si (CH 2 CH 2 CF 3 )-(OSSiOCH 3 (CH 2 C H 2 CF 3 )) 4 —OCH 3 and the like.
- a compound having only a hydrolyzable group a compound having a siloxane skeleton-containing group and a hydrolyzable group; a compound having two siloxane skeleton-containing groups and a hydrolyzable group; a hydrocarbon chain-containing group and a hydrolyzable group Or a compound having two hydrocarbon chain-containing groups and a hydrolyzable group is preferable, and a compound having only a hydrolyzable group is more preferable.
- the molar ratio of the metal compound (b) to the organosilicon compound (a) (metal compound (b) / organosilicon compound (a)) is preferably 0.1 or more, more preferably 1 or more, even more preferably. Is 5 or more, more preferably 8 or more, and preferably 100 or less, more preferably 80 or less, even more preferably 70 or less, still more preferably 60 or less, and particularly preferably 50 or less.
- Preferred embodiments of the coating composition include the following embodiments.
- the metal compound (b) is a compound represented by the following formula (II-2)
- the fluorocarbon-containing group represented by R b10 has 1 to 8 (preferably 1 to 6) carbon atoms.
- the aspect which is at least 1 sort (s) chosen from the group which consists of the compound which is these, and its hydrolysis-condensation product is preferable.
- the organosilicon compound (a) is preferably a compound represented by the following formula (I-II).
- the molar ratio of the organosilicon compound (a) to the metal compound (b) (metal compound (b) / organosilicon compound (a)) is preferably 0.1 or more, more preferably 5 or more. More preferably, it is 8 or more, preferably 80 or less, more preferably 60 or less, still more preferably 50 or less.
- the metal compound (b) is at least one selected from the group consisting of a compound represented by the following formula (II-1) and a hydrolysis condensate thereof, and the metal compound (b) and the organosilicon compound (II-1) and a hydrolysis condensate thereof, and the metal compound (b) and the organosilicon compound (II-1) and a hydrolysis condensate thereof, and the metal compound (b) and the organosilicon compound ( An embodiment in which the molar ratio of a) (metal compound (b) / organosilicon compound (a)) is 10 or more is preferred.
- R b2 , A b1 , Z b2 and k are as defined above.
- the organosilicon compound (a) is preferably a compound represented by the following formula (I-II).
- the molar ratio of the metal compound (b) to the organosilicon compound (a) is 10 or more, preferably 15 or more, and 18 or more. It is more preferable that The molar ratio (metal compound (b) / organosilicon compound (a)) is preferably 80 or less, more preferably 60 or less, and still more preferably 50 or less.
- organosilicon compound is a compound represented by the following formula (II) is also preferable.
- a a1 , Z a2 , R s3 , R s4 , R s5 , m1 and n1 are as defined above.
- the molar ratio of the organosilicon compound (a) to the metal compound (b) (metal compound (b) / organosilicon compound (a)) is preferably 0.1 or more, more preferably 5 or more. More preferably, it is 8 or more, preferably 80 or less, more preferably 60 or less, still more preferably 50 or less.
- hydrophilic organic solvents such as alcohol solvents, ether solvents, ketone solvents, ester solvents, amide solvents, water and the like. These may be used alone or in combination of two or more.
- the alcohol solvent include methanol, ethanol, propanol, isopropyl alcohol, butanol, ethylene glycol, propylene glycol, and diethylene glycol.
- the ether solvent include dimethoxyethane, tetrahydrofuran, and dioxane.
- Examples of the solvent include acetone and methyl ethyl ketone, examples of the ester solvent include ethyl acetate and butyl acetate, and examples of the amide solvent include dimethylformamide.
- examples of alcohol solvents and ketone solvents are preferable and may contain water.
- the solvent (c) is preferably 0.01 parts by mass or more, more preferably 0.05 parts by mass or more, further with respect to 1 part by mass in total of the organosilicon compound (a) and the metal compound (b).
- it is 0.1 mass part or more, it is preferable that it is 20 mass parts or less, More preferably, it is 10 mass parts or less, More preferably, it is 5 mass parts or less.
- the amount of the solvent (c) is within this range, the thickness of the transparent film can be easily controlled.
- the catalyst (d) is not particularly limited as long as it can act as a hydrolysis catalyst for a hydrolyzable group bonded to a silicon atom, and examples thereof include acidic compounds; basic compounds; organometallic compounds; Examples of the acidic compound include inorganic acids such as hydrochloric acid and nitric acid; organic acids such as acetic acid; Examples of the basic compound include ammonia, amines, and the like.
- organometallic compound examples include organometallic compounds having a metal element such as Al, Fe, Zn, Sn as a central metal, organoaluminum compounds such as aluminum acetylacetone complex and aluminum ethylacetoacetate complex; iron octylate, etc.
- organoaluminum compounds such as aluminum acetylacetone complex and aluminum ethylacetoacetate complex
- iron octylate etc.
- a catalyst (d) an organometallic compound and an acidic compound are preferable, and an organoaluminum compound and hydrochloric acid are more preferable.
- the catalyst (d) is preferably 0.0001 parts by mass or more, more preferably 0.0002 parts by mass or more, further with respect to 100 parts by mass in total of the organosilicon compound (a) and the metal compound (b).
- it is 0.001 mass part or more, it is preferable that it is 20 mass parts or less, More preferably, it is 10 mass parts or less, More preferably, it is 5 mass parts or less.
- a catalyst (d) is 0.001 mass part or more with respect to a total of 100 mass parts of an organosilicon compound (a) and a metal compound (b).
- the catalyst (d) is preferably 0.0001 parts by mass or more with respect to 100 parts by mass in total of the organosilicon compound (a) and the metal compound (b). More preferably, it is 0.0002 mass part or more, More preferably, it is 0.001 mass part or more, It is preferable that it is 0.1 mass part or less, More preferably, it is 0.05 mass part or less.
- the antioxidant when the organosilicon compound (a) and the metal compound (b) are brought into contact with the base material, the antioxidant, the rust inhibitor, the ultraviolet absorber, the light stabilizer, the antibacterial agent within the range not impairing the effects of the present invention.
- Various additives such as fungicides, antibacterial agents, biological adhesion inhibitors, deodorants, pigments, flame retardants and antistatic agents may coexist.
- antioxidants examples include phenol-based antioxidants, sulfur-based antioxidants, phosphorus-based antioxidants, hindered amine-based antioxidants, and the like.
- phenolic antioxidant examples include n-octadecyl-3- (4-hydroxy-3,5-di-t-butylphenyl) propionate, 2,6-di-t-butyl-4-methylphenol, 2, 2-thio-diethylene-bis- [3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate], tri-ethylene glycol-bis- [3- (3-t-butyl-5-methyl -4-hydroxyphenyl) propionate], 3,9-bis [2- ⁇ 3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy ⁇ -1,1-dimethylethyl] -2, 4,8,10-tetraoxaspiro [5.5] undecane, tetrakis ⁇ 3- (3,5-di-tert-butyl-4-hydroxyphenyl) -propionic acid ⁇ pentaeryth Cyl ester, 2-t-butyl-6-
- sulfur-based antioxidant examples include 3,3′-thiodipropionic acid di-n-dodecyl ester, 3,3′-thiodipropionic acid di-n-tetradecyl ester, and 3,3′-thiodipropion.
- examples include acid di-n-octadecyl ester and tetrakis (3-dodecylthiopropionic acid) pentaerythritol ester.
- Examples of the phosphorus antioxidant include tris (2,4-di-t-butylphenyl) phosphite, bis (2,4-di-t-butylphenyl) pentaerythritol diphosphite, bis (2,6-di-).
- t-butyl-4-methylphenyl) pentaerythritol diphosphite bis (2,4-di-cumylphenyl) pentaerythritol diphosphite, tetrakis (2,4-di-t-butylphenyl) -4,4'-biphenylene diphosphonite, bis -[2,4-di-t-butyl, (6-methyl) phenyl] ethyl phosphite and the like.
- hindered amine antioxidant examples include sebacic acid bis (2,2,6,6-tetramethyl-4-piperidyl) ester (melting point: 81 to 86 ° C.), 2,2,6,6-tetramethyl-4- Piperidyl methacrylate (melting point: 58 ° C.), poly [ ⁇ 6- (1,1,3,3-tetramethylbutyl) amino-1,3,5-triazine-2,4-diyl ⁇ ⁇ (2,2,6, 6-tetramethyl-4-piperidyl) imino ⁇ -1,6-hexamethylene ⁇ (2,2,6,6-tetramethyl-4-piperidyl) imino ⁇ ] and the like.
- the rust inhibitor examples include alkanolamines such as triethanolamine; quaternary ammonium salts; alkanethiols; imidazoles such as imidazoline, imidazole, alkylimidazoline derivatives, benzimidazole, 2-mercaptobenzimidazole, and benzotriazole; metavanadic acid Sodium; bismuth citrate; phenol derivatives; aliphatic amines such as alkylamines and polyalkenylamines, aromatic amines, ethoxylated amines, cyanoalkylamines, cyclohexylamine benzoate, aliphatic diamines such as alkylenediamine, aromatic diamines, etc.
- alkanolamines such as triethanolamine
- quaternary ammonium salts such as imidazoline, imidazole, alkylimidazoline derivatives, benzimidazole, 2-mercaptobenzimidazole, and benzotri
- Examples of the ultraviolet absorber / light stabilizer include 2- (5-methyl-2-hydroxyphenyl) benzotriazole, 2- [2-hydroxy-3,5-bis ( ⁇ , ⁇ -dimethylbenzyl) phenyl].
- Examples of the fungicide / antibacterial agent include 2- (4-thiazolyl) benzimidazole, sorbic acid, 1,2-benzisothiazolin-3-one, (2-pyridylthio-1-oxide) sodium, dehydroacetic acid, 2-methyl -5-chloro-4-isothiazolone complex, 2,4,5,6-tetrachlorophthalonitrile, methyl 2-benzimidazole carbamate, methyl 1- (butylcarbamoyl) -2-benzimidazole carbamate, mono or dibromocyano
- Examples include acetamides, 1,2-dibromo-2,4-dicyanobutane, 1,1-dibromo-1-nitropropanol and 1,1-dibromo-1-nitro-2-acetoxypropane.
- biological adhesion inhibitor examples include tetramethylthiuram disulfide, bis (N, N-dimethyldithiocarbamate) zinc, 3- (3,4-dichlorophenyl) -1,1-dimethylurea, dichloro-N-((dimethylamino ) Sulfonyl) fluoro-N- (P-tolyl) methanesulfenamide, pyridine-triphenylborane, N, N-dimethyl-N′-phenyl-N ′-(fluorodichloromethylthio) sulfamide, cuprous thiocyanate ( 1), cuprous oxide, tetrabutylthiuram disulfide, 2,4,5,6-tetrachloroisophthalonitrile, zinc ethylenebisdithiocarbamate, 2,3,5,6-tetrachloro-4- (methyl) Sulfonyl) pyridine, N- (2,4,6-trichloroph
- deodorizer examples include lactic acid, succinic acid, malic acid, citric acid, maleic acid, malonic acid, ethylenediaminepolyacetic acid, alkane-1,2-dicarboxylic acid, alkene-1,2-dicarboxylic acid, cycloalkane-1 , 2-dicarboxylic acid, cycloalkene-1,2-dicarboxylic acid, organic acids such as naphthalenesulfonic acid; fatty acid metals such as zinc undecylenate, zinc 2-ethylhexanoate, zinc ricinoleate; iron oxide, iron sulfate, Zinc oxide, zinc sulfate, zinc chloride, silver oxide, copper oxide, metal (iron, copper, etc.) chlorophyllin sodium, metal (iron, copper, cobalt etc.) phthalocyanine, metal (iron, copper, cobalt etc.) tetrasulfonic acid phthalocyanine, Metal compounds such as titanium dioxide, visible light responsive
- the pigment examples include carbon black, titanium oxide, phthalocyanine pigment, quinacridone pigment, isoindolinone pigment, perylene or perine pigment, quinophthalone pigment, diketopyrrolo-pyrrole pigment, dioxazine pigment, disazo condensation pigment, Examples include benzimidazolone pigments.
- flame retardant examples include decabromobiphenyl, antimony trioxide, phosphorus flame retardant, aluminum hydroxide and the like.
- antistatic agent examples include quaternary ammonium salt type cationic surfactants, betaine type amphoteric surfactants, alkyl phosphate type anionic surfactants, primary amine salts, secondary amine salts, thirds.
- Cationic surfactants such as quaternary amine salts, quaternary amine salts and pyridine derivatives, sulfated oils, soaps, sulfated ester oils, sulfated amide oils, sulfated ester salts of olefins, fatty alcohol sulfate esters, alkyl sulfates
- Anionic surfactants such as ester salts, fatty acid ethyl sulfonates, alkyl naphthalene sulfonates, alkyl benzene sulfonates, oxalate sulfonates and phosphate ester salts, partial fatty acid esters of polyhydric alcohols, fatty alcohol
- additives lubricants, fillers, plasticizers, nucleating agents, antiblocking agents, foaming agents, emulsifiers, brighteners, binders, and the like may coexist.
- the content of the additives is usually 0.1 to 70% by mass in the coating composition containing the organosilicon compound (a) and the metal compound (b), preferably 0.8. It is 1 to 50% by mass, more preferably 0.5 to 30% by mass, and further preferably 2 to 15% by mass.
- the total content of the organosilicon compound (a) and the metal compound (b) (when the solvent (c) is included, the total content of the organosilicon compound (a), the metal compound (b), and the solvent (c)) is In a coating composition, it is 60 mass% or more normally, Preferably it is 75 mass% or more, More preferably, it is 85 mass% or more, More preferably, it is 95 mass% or more.
- Examples of the method for bringing the organosilicon compound (a) and the metal compound (b) into contact with the substrate include spin coating, dip coating, spray coating, roll coating, bar coating, and die coating.
- the spin coating method and the spray coating method are preferable. According to the spin coating method and the spray coating method, it becomes easy to form a transparent film having a predetermined thickness.
- the coating composition may be further diluted as necessary.
- the dilution factor is, for example, 2 to 100 times, preferably 5 to 50 times that of the composition before dilution.
- the solvent illustrated as a solvent (c) can be used suitably.
- organosilicon compound (a) and the metal compound (b) By leaving the organosilicon compound (a) and the metal compound (b) in contact with the base material in the air, moisture in the air is taken in and the hydrolyzable group is hydrolyzed, and siloxane A skeleton is formed. When allowed to stand, it may be kept at 40 to 250 ° C.
- the transparent coating of the present invention thus obtained is superior in terms of weather resistance than a coating obtained from a conventional fluorine coating agent.
- the transparent film of the present invention has a trialkylsilyl group-containing molecular chain or a molecular chain in which an alkyl group in a trialkylsilyl group-containing molecular chain is replaced with a fluoroalkyl group. Since the change in the contact angle before and after irradiation is controlled within a certain range, the chemical and physical durability is high and the wear resistance is excellent. The wear resistance can be confirmed by, for example, a wear test using an eraser.
- the transparent film of the present invention is excellent in the slipperiness of the droplets.
- the slipperiness of the droplet can be confirmed by, for example, the droplet sliding speed when the droplet is placed on the transparent film of the present invention and tilted from 90 ° to the horizontal.
- the transparent film of the present invention has high chemical / physical durability and excellent slipperiness of the droplets, the slipperiness when rubbed with a finger is also good.
- the transparent film of the present invention is usually formed on a substrate, and a transparent film-treated substrate in which the transparent film of the present invention is formed on a substrate is also included in the scope of the present invention.
- the shape of the substrate may be either a flat surface or a curved surface, or may be a three-dimensional structure in which a large number of surfaces are combined.
- the substrate may be composed of any organic material or inorganic material.
- the organic material examples include acrylic resin, polycarbonate resin, polyester resin, styrene resin, acrylic-styrene copolymer resin, cellulose Thermoplastic resins such as resins, polyolefin resins, polyvinyl alcohol, etc .; thermosetting resins such as phenol resins, urea resins, melamine resins, epoxy resins, unsaturated polyesters, silicone resins, urethane resins; Are ceramics; glass; metals such as iron, silicon, copper, zinc, and aluminum; alloys containing the metals; The substrate may be subjected to an easy adhesion treatment in advance. Examples of the easy adhesion treatment include hydrophilic treatment such as corona treatment, plasma treatment, and ultraviolet treatment.
- primer treatment with a resin, a silane coupling agent, tetraalkoxysilane, or the like may be used.
- durability such as moisture resistance and alkali resistance can be further improved.
- the layer formed using the composition for base layer formation containing the component (P) which can form siloxane skeleton is preferable.
- the layer formed using the composition for base layer formation containing the (P1) component which consists of a compound represented by following formula (III) and / or its partial hydrolysis-condensation product, for example is preferable.
- X P2 independently represents a halogen atom, an alkoxy group or an isocyanate group.
- X P2 is preferably a chlorine atom, an alkoxy group having 1 to 4 carbon atoms or an isocyanate group, and the four X P2 are preferably the same.
- compound (III) As such a compound represented by the above general formula (III) (hereinafter sometimes referred to as compound (III)), specifically, Si (NCO) 4 , Si (OCH 3 ) 4 , Si (OC 2). H 5 ) 4 and the like are preferably used.
- compound (III) may be used alone or in combination of two or more.
- the component (P1) contained in the primer layer forming composition may be a partially hydrolyzed condensate of compound (III).
- the partial hydrolysis-condensation product of compound (III) can be obtained by applying a general hydrolysis-condensation method using an acid or a base catalyst.
- the degree of condensation (degree of multimerization) of the partially hydrolyzed condensate needs to be such that the product is dissolved in the solvent.
- Component (P1) may be compound (III) or a partial hydrolysis condensate of compound (III), and a mixture of compound (III) and its partial hydrolysis condensate, for example, It may be a partially hydrolyzed condensate of compound (III) containing compound (III) of the reaction.
- a commercial item as a compound shown with general formula (III), and its partial hydrolysis-condensation product, It is possible to use such a commercial item for this invention.
- the underlayer-forming composition comprises the component (P1), a compound represented by the following formula (IV) (hereinafter sometimes referred to as compound (IV)) and / or a partially hydrolyzed condensate thereof. Or a partially hydrolyzed cocondensate of the component (P1) and the component (P2) (however, the component (P1) and / or the compound (IV) may be included).
- the composition may also be included.
- Compound (IV) is a compound having hydrolyzable silyl groups or silanol groups at both ends with a divalent organic group in between.
- Examples of the hydrolyzable group represented by X P3 in formula (IV) include the same groups or atoms as those of X P2 above.
- X P3 is preferably an alkoxy group or an isocyanate group, and particularly preferably an alkoxy group.
- 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. These are appropriately selected and used according to the purpose of manufacture, application and the like.
- the X P3 to a plurality present in the compound (IV) may be different groups in the same group, it is preferable in terms of ease availability of the same group.
- compound (IV) specifically, (CH 3 O) 3 SiCH 2 CH 2 Si (OCH 3 ) 3 , (OCN) 3 SiCH 2 CH 2 Si (NCO) 3 , Cl 3 SiCH 2 CH 2 SiCl 3 include (C 2 H 5 O) 3 SiCH 2 CH 2 Si (OC 2 H 5) 3, (CH 3 O) 3 SiCH 2 CH 2 CH 2 CH 2 CH 2 Si (OCH 3) 3 , etc. .
- compound (IV) may be used alone or in combination of two or more.
- the component contained in the primer layer forming composition may be a partially hydrolyzed condensate of compound (IV).
- the partially hydrolyzed condensate of compound (IV) can be obtained by the same method as described in the production of the partially hydrolyzed condensate of compound (III).
- the degree of condensation (degree of multimerization) of the partially hydrolyzed condensate must be such that the product is dissolved in the solvent.
- Component (P) may be compound (IV) or a partial hydrolysis condensate of compound (III), and a mixture of compound (IV) and its partial hydrolysis condensate, for example, It may be a partially hydrolyzed condensate of compound (IV) containing compound (IV) of the reaction.
- various polysilazanes capable of obtaining an oxide film mainly composed of silicon similar to the compound (III) may be used for the underlayer.
- the primer layer-forming composition usually contains an organic solvent in addition to the solid content as a layer constituent component in consideration of economy, workability, ease of controlling the thickness of the resulting primer layer, and the like.
- the organic solvent is not particularly limited as long as it dissolves the solid content contained in the primer layer forming composition.
- an organic solvent the same compound as the composition for water-repellent film formation is mentioned.
- the organic solvent is not limited to one kind, and two or more kinds of solvents having different polarities and evaporation rates may be mixed and used.
- composition for forming a primer layer contains a partial hydrolysis condensate or a partial hydrolysis cocondensate, it may contain a solvent used for producing them.
- composition for forming a primer layer even if it does not contain a partial hydrolysis condensate or partial hydrolysis cocondensate, in order to promote the hydrolysis cocondensation reaction, It is also preferable to blend a catalyst such as an acid catalyst that is generally used. Even when a partially hydrolyzed condensate or a partially hydrolyzed cocondensate is included, when the catalyst used for the production thereof does not remain in the composition, it is preferable to add a catalyst.
- the underlayer-forming composition may contain water for the above-mentioned components to undergo a hydrolysis condensation reaction or a hydrolysis cocondensation reaction.
- the underlayer using the primer layer forming composition As a method for forming the underlayer using the primer layer forming composition, a known method for an organosilane compound-based surface treatment agent can be used.
- the composition for forming the underlayer is applied to the surface of the substrate by methods such as brush coating, flow coating, spin coating, dip coating, squeegee coating, spray coating, and hand coating, and is necessary in the air or in a nitrogen atmosphere.
- the base layer can be formed by curing after drying according to the above. Curing conditions are appropriately controlled depending on the type and concentration of the composition used.
- the primer layer forming composition may be cured simultaneously with the water repellent film forming composition.
- the thickness of the primer layer is not particularly limited as long as it can impart moisture resistance, adhesion, and barrier properties such as alkali from the substrate to the water-repellent film formed thereon.
- the transparent film of the present invention can achieve both water repellency / oil repellency, heat resistance and light resistance (weather resistance), and is a basis for display devices such as touch panel displays, optical elements, semiconductor elements, building materials, automobile parts, nanoimprint technology, and the like. Useful as a material.
- the transparent coating of the present invention is suitably used as an article such as a body, window glass (front glass, side glass, rear glass), mirror, bumper, etc. in transportation equipment such as trains, automobiles, ships, and aircraft. Moreover, it can also be used for outdoor uses, such as a building outer wall, a tent, a solar power generation module, a sound insulation board, and concrete. It can also be used for fishing nets, insect nets, water tanks, and the like.
- it can be used for various indoor facilities such as kitchens, bathrooms, washstands, mirrors, toilet articles, ceramics such as chandeliers and tiles, artificial marble, and air conditioners. It can also be used as an antifouling treatment for jigs, inner walls, pipes and the like in factories. It is also suitable for goggles, glasses, helmets, slingshots, textiles, umbrellas, play equipment, soccer balls and the like. Furthermore, it can also be used as an anti-adhesive agent for various packaging materials such as food packaging materials, cosmetic packaging materials, and the inside of pots.
- a steel wool testing machine manufactured by Daiei Seiki Co., Ltd.
- an HB pencil with an eraser Mitsubishi Pencil Co., Ltd.
- a wear test was performed with a load of 500 g, and the number of times until the initial contact angle became ⁇ 15 ° or less was measured.
- Tactile sensation and finger slipperiness The surface of the transparent film was rubbed with fingers, and the tactile sensation and finger slipperiness were evaluated by sensory evaluation.
- the evaluation criteria were as follows. ⁇ : Glide very well, ⁇ : Glide, ⁇ : Feeling caught, ⁇ : Not glide
- Synthesis example 1 0.86 g of sodium hydroxide was added to 13.4 g of tetraethyl orthosilicate (tetraethoxysilane), and the mixture was stirred at room temperature for 2 hours. The resulting solution was diluted 0.4 times with heptane while cooling to ⁇ 40 ° C. with dry ice.
- Synthesis example 2 A three-necked flask was charged with 4.8 g of trimethylsilanol and 56 mL of tetrahydrofuran (THF) and purged with nitrogen. The solution was cooled to ⁇ 40 ° C., and 33.6 mL of n-butyllithium (n-BuLi) hexane solution (1.6 mol / L) was added dropwise. The mixture was stirred for 15 minutes and returned to room temperature to obtain a precursor solution. A three-necked flask was charged with 20 g of 1,7-dichlorooctamethyltetrasiloxane and 80 mL of THF, cooled to ⁇ 30 ° C., and the precursor solution was added dropwise.
- THF tetrahydrofuran
- TEOS tetraethoxysilane
- sodium hydroxide 7.74 g
- TEOS tetraethoxysilane
- 5.0 g of Precursor 2 dissolved in 7.4 mL of heptane was added dropwise.
- the obtained reaction product was filtered, and heptane was distilled off at 6 hPa and 50 ° C. to obtain a compound 2 represented by the following formula.
- Synthesis example 3 A three-necked flask equipped with a condenser was charged with 3.94 g of trichloroisocyanuric acid, and nitrogen substitution was performed. 50 mL of dichloromethane was charged from a septum, stirred, and 5.0 g of tris (trimethylsiloxy) silane was added. After stirring for 1 hour, it was filtered. The filtrate was added dropwise while cooling the filtrate in an ice bath containing 150 mL of diethyl ether, 50 mL of ion exchange water, and 1.87 g of triethylamine. Stir at room temperature for 1 hour. It was washed with ion-exchanged water, dehydrated with magnesium sulfate, and concentrated at 150 mmHg and 25 ° C. to obtain 5.8 g of the intended intermediate 3 (silanol 1).
- Example 1 To 3.88 mL (3.12 g) of methyl ethyl ketone as the solvent (c), 2.5 ⁇ 10 ⁇ 4 mol (0.14 g) of the compound 1 as the organosilicon compound (a) was used as the metal compound (b). Tetraethyl orthosilicate (tetraethoxysilane) 5 ⁇ 10 ⁇ 3 mol (1.04 g), 25% isopropyl alcohol solution of ethyl acetoacetate aluminum diisopropylate as catalyst (d) (“ALCH-75 manufactured by Kawaken Fine Chemical Co., Ltd.) 200 ⁇ L) was added and stirred for 24 hours to prepare Sample Solution 1.
- Tetraethyl orthosilicate tetraethoxysilane
- Comparative Example 1 Octyltriethoxysilane 0.5 mL, tetraethyl orthosilicate 7.05 mL, 0.01 M hydrochloric acid 9.5 mL, and ethanol 17 mL were mixed. The obtained mixed solution was diluted 8 times with ethanol to obtain a comparative sample solution 1.
- Comparative Example 2 Optool DSX-E (manufactured by Daikin) 0.2 g and Novec 7200 (manufactured by 3M) 39.8 g were stirred at room temperature to obtain a comparative coating solution 2.
- Sample solution 1, 3, 4, or comparative sample solution 1 is spin-coated on an alkali-cleaned glass substrate (Corning “EAGLE XG”) at 3000 rpm for 20 seconds using a spin coater (Mikasa). After leaving this still at room temperature for one day, it was further cured at 120 ° C. to obtain the transparent film of the present invention or the film of the comparative example.
- Table 1 shows the contact angle, abrasion resistance, slipperiness of liquid droplets, tactile sensation, and finger slipperiness of the obtained film.
- the obtained transparent film was irradiated with light for 100 hours while adjusting the lamp intensity to 250 W and the internal temperature to 50 to 60 ° C. It was.
- the obtained transparent film was allowed to stand at a temperature of 200 ° C. for 24 hours and subjected to a heat resistance test.
- Table 2 shows the wear resistance, slipperiness of droplets, tactile sensation and finger slipperiness.
- Tables 2 and 3 show the contact angle and rate of change of the film before and after the weather resistance test.
- Mercury lamp irradiation test Sample solutions 2 and 3 were diluted 30-fold with methyl ethyl ketone, respectively, to obtain coating solutions 2 and 3. Further, the sample solution 4 was diluted 20 times with methyl ethyl ketone to obtain a coating solution 4.
- An alkali-cleaned glass substrate (“EAGLE XG” manufactured by Corning) was spin-coated with coating solution 2 to 4 or comparative coating solution 2 using a spin coater (manufactured by MIKASA) at 3000 rpm for 20 seconds. was allowed to stand at room temperature for 1 day, and further cured at 120 ° C. to obtain a transparent film of the present invention or a film of a comparative example.
- a uniform light irradiation unit (USHIO Inc.) was attached to a mercury lamp (USHIO "SP-9 250DB"), and a sample was installed at a distance of 17.5 cm from the lens.
- the light intensity of 200-800 nm was measured using an intensity meter (“VEGA” manufactured by OPHIL), and it was 200 mW / cm 2 .
- the sample was irradiated with a mercury lamp for 4 hours or 6 hours in an air atmosphere at a temperature of 20 to 40 ° C. and a humidity of 30 to 75%.
- the transparent film of the present invention can achieve both water repellency / oil repellency, heat resistance and light resistance (weather resistance), and is a basis for display devices such as touch panel displays, optical elements, semiconductor elements, building materials, automobile parts, nanoimprint technology, and the like. Useful as a material.
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Abstract
Description
すなわち、本発明に係る透明皮膜は、ポリシロキサン骨格と、前記ポリシロキサン骨格を形成するケイ素原子のうち一部のケイ素原子に結合するトリアルキルシリル基含有分子鎖とを含む透明皮膜であって、トリアルキルシリル基含有分子鎖中のアルキル基がフルオロアルキル基に置き換わっていてもよく、透明皮膜上の液滴の初期接触角をA0、温度200℃で24時間静置した後の接触角をBH、強度250Wのキセノンランプを温度で100時間照射した後の接触角をBLとしたときに、
(BH-A0)/A0×100(%)≧-27(%)、および、
(BL-A0)/A0×100(%)≧-15(%)
の少なくとも一方を満足することを特徴とする。
(Bz1-A1)/A1×100(%)≧-9(%)
[式(I-I)中、複数のAa1は、それぞれ独立に、加水分解性基を表す。Za2は、トリアルキルシリル基含有分子鎖、炭化水素鎖含有基、シロキサン骨格含有基又は加水分解性基を表し、Za2が加水分解性基の場合、Za2とAa1とは、同一であっても異なっていてもよい。また、複数の式(I)間でRaとZa2とは同一であっても異なっていてもよい。Rs3は、それぞれ独立に、炭素数1以上、4以下のアルキル基を表す。Rs4は、炭素数1以上、10以下の2価の炭化水素基を表し、Rs4中のメチレン基(-CH2-)は、酸素原子で置き換わっていてもよい。Rs5は、それぞれ独立に、炭素数1以上、4以下のアルキル基を表す。m、nは、それぞれ独立に、0以上の整数を表す。ただし添字n1、m1を付して括弧でくくられた各繰り返し単位の存在順序は、式中において任意である。]
(BH-A0)/A0×100(%)≧-27(%)、および、
(BL-A0)/A0×100(%)≧-15(%)
の少なくとも一方を満足する。
なお、接触角は、液量3μLの水を用い、θ/2法にて測定した値を意味する。また、初期接触角A0は、耐熱試験、耐光試験を行っていない透明皮膜の接触角を意味するものとする。
耐光試験後接触角BLは、75°以上であることが好ましく、より好ましくは90°以上、さらに好ましくは95°以上であり、通常、180°以下であることが好ましい。
(Bz1-A1)/A1×100(%)≧-9(%)
本発明の透明皮膜は、特に耐光性が良好であり、高強度の光を照射した場合でも、撥水・撥油特性が低下しにくい。前記4時間照射前後の接触角度変化率((Bz1-A1)/A1×100(%))は、-9.0(%)以上であることが好ましく、より好ましくは-7%以上、さらに好ましくは-5%以上、特に好ましくは-3%以上である。
(Bz2-A1)/A1×100(%)>-18(%)
前記6時間照射前後の接触角変化率((Bz2-A1)/A1×100(%))は、より好ましくは-16%以上、さらに好ましくは-10%以上、よりいっそう好ましくは-7%以上、特に好ましくは-5%以上であり、例えば-1%以下であってもよい。
300nm以下の(波長)領域に輝線を有する水銀ランプとしては、ウシオ電機社製「SP-9 250DB」及びその同等のものが挙げられる。
前記トリアルキルシリル基に含まれるアルキル基としては、具体的には、メチル基、エチル基、プロピル基、ブチル基等が挙げられる。また、トリアルキルシリル基中の3つのアルキル基は、互いに同一でも異なっていてもよいが、同一であることが好ましい。さらに、トリアルキルシリル基には、メチル基が少なくとも1つ含まれていることが好ましく、より好ましくは2つ以上であり、3つのアルキル基が全てメチル基であることが特に好ましい。
またこの場合、トリアルキルシリル基含有分子鎖に含まれるトリアルキルシリル基の数は、好ましくは2個以上、より好ましくは3個となる場合もある。
また、ジアルキルシロキサン鎖中、ジアルキルシリルオキシ基の繰り返し数は、1以上であり、100以下であることが好ましく、より好ましくは80以下、さらに好ましくは50以下、特に好ましくは20以下、最も好ましくは15以下である。
Rs2のジアルキルシロキサン鎖、および、Rs2のジアルキルシロキサン鎖の酸素原子を置き換えていてもよい2価の炭化水素基は、上記説明した範囲から適宜選択可能である。
Rs4は、炭素数1以上、10以下の2価の炭化水素基を表し、Rs4中のメチレン基(-CH2-)は、酸素原子で置き換わっていてもよい。Rs5は、それぞれ独立に、炭素数1以上、4以下のアルキル基を表す。m1、n1は、それぞれ独立に、0以上の整数を表す。*は、ケイ素原子との結合手を表す。ただし添字n1、m1を付して括弧でくくられた各繰り返し単位の存在順序は、式中において任意である。]
Rs9は、炭素数1以上、10以下の2価の炭化水素基を表し、Rs9中のメチレン基(-CH2-)は、酸素原子で置き換わっていてもよい。Rs10は、それぞれ独立に、炭素数1以上、4以下のアルキル基を表す。m2、n2は、それぞれ独立に、0以上の整数を表す。*は、ケイ素原子との結合手を表す。ただし添字n2、m2を付して括弧でくくられた各繰り返し単位の存在順序は、式中において任意である。]
Rs5及びRs10のアルキル基は、トリアルキルシリル基のアルキル基として上記説明した範囲から適宜選択でき、*-Si(Rs5)3又は、*-Si(Rs10)3に含まれるアルキル基の炭素数は、1以上、4以下であることが好ましく、より好ましくは1以上、3以下、さらに好ましくは1以上、2以下である。また、トリアルキルシリル基に含まれる3つのアルキル基の合計の炭素数は、9以下であることが好ましく、より好ましくは6以下、さらに好ましくは4以下である。さらに、*-Si(Rs5)3には、メチル基が少なくとも1つ含まれていることが好ましく、より好ましくは2つ以上であり、3つのアルキル基が全てメチル基であることが特に好ましい。
m1及びm2は、0以上4以下であることが好ましく、0以上、3以下であることがより好ましい。また、n1及びn2は、1以上、100以下であることが好ましく、より好ましくは1以上、80以下、さらに好ましくは1以上、50以下、特に好ましくは1以上、30以下、最も好ましくは1以上、20以下である。
なお添字n1、m1を付して括弧でくくられた各繰り返し単位の存在順序、及び、添字n2、m2を付して括弧でくくられた各繰り返し単位の存在順序は、式中に記載した通りの順序であってもよい。
シロキサン骨格含有基は、シロキサン骨格の一部に2価の炭化水素基を含んでいてもよい。具体的には、シロキサン骨格の一部の酸素原子が2価の炭化水素基で置き換わっていてもよい。シロキサン骨格の一部の酸素原子を置き換えていてもよい2価の炭化水素基としては、トリアルキルシリル基含有分子鎖に含まれるジアルキルシロキサン鎖の酸素原子を置き換えていてもよい2価の炭化水素基と同様の基を好ましく挙げることができる。
また、Rs6は、炭化水素基であることが好ましい。Rs6の炭化水素基に含まれるメチレン基は、酸素原子に置き換わっている場合もある。
なお、炭化水素鎖部分の炭素数とは、酸素非置換型の炭化水素鎖含有基では炭化水素基(炭化水素鎖)を構成する炭素原子の数を意味し、酸素置換型の炭化水素鎖含有基では、酸素原子をメチレン基(-CH2-)と仮定して数えた炭素原子の数を意味するものとする。
以下、特に断りがない限り、酸素非置換型の炭化水素鎖含有基(すなわち1価の炭化水素基)を例にとって炭化水素鎖含有基について説明するが、いずれの説明でも、そのメチレン基(-CH2-)のうち一部を酸素原子に置き換えることが可能である。
中でも、式(1)中、Za1は、シロキサン骨格含有基又は-O-基であることが好ましく、-O-基であることがより好ましい。
また、Zb1は、シロキサン骨格含有基、ヒドロキシ基又は-O-基であることが好ましく、ヒドロキシ基又は-O-基であることがより好ましい。
フルオロアルコキシアルキル基としては、例えばフルオロメトキシC5-20アルキル基、フルオロエトキシC5-20アルキル基、フルオロプロポキシC5-20アルキル基、フルオロブトキシC5-20アルキル基などが挙げられる。
フルオロアルキルシリルアルキル基としては、例えばフルオロメチルシリルC5-20アルキル基、フルオロエチルシリルC5-20アルキル基、フルオロプロピルシリルC5-20アルキル基、フルオロブチルシリルC5-20アルキル基、フルオロペンチルシリルC5-20アルキル基、フルオロヘキシルシリルC5-20アルキル基、フルオロへプチルシリルC5-20アルキル基、フルオロオクチルシリルC5-20アルキル基などが挙げられる。
フルオロアルキルカルボニルオキシアルキル基としては、フルオロメチルカルボニルオキシC5-20アルキル基、フルオロエチルカルボニルオキシC5-20アルキル基、フルオロプロピルカルボニルオキシC5-20アルキル基、フルオロブチルカルボニルオキシC5-20アルキル基などが挙げられる。
フルオロアルキルアリール基としては、フルオロC1-8アルキルフェニル基、フルオロC1-8アルキルナフチル基が挙げられ、フルオロアルキルアルケニル基としては、フルオロC1-17アルキルビニル基が挙げられ、フルオロアルキルアルキニル基としては、フルオロC1-17アルキルエチニル基が挙げられる。
また、前記オリゴマー残基がアルコキシ基を有する場合、そのアルコキシ基はメトキシ基、エトキシ基、プロポキシ基、ブトキシ基などが挙げられ、好ましくはメトキシ基、エトキシ基等である。前記オリゴマー残基は、これらアルコキシ基の1種又は2種以上を有することができ、好ましくは1種を有する。
Xとしては、加水分解性基又は炭素数1~12の(好ましくは炭素数1~4)含フッ素アルキル基が好ましい。
Zb11としては、加水分解性基、炭素数1~12の含フッ素アルキル基又は-O-基が好ましい。
有機ケイ素化合物(a)において、中心ケイ素原子に結合する加水分解性基の個数は、1以上であり、2以上であることが好ましく、通常、3以下であることが好ましい。
また、複数の式(I-II)間でRaとZa2とは同一であっても異なっていてもよい。Rs8は、それぞれ独立に、炭素数1以上、4以下のアルキル基を表す。Rs9は、炭素数1以上、10以下の2価の炭化水素基を表し、Rs9中のメチレン基(-CH2-)は、酸素原子で置き換わっていてもよい。Rs10は、それぞれ独立に、炭素数1以上、4以下のアルキル基を表す。m2、n2は、それぞれ独立に、0以上の整数を表す。ただし添字n2、m2を付して括弧でくくられた各繰り返し単位の存在順序は、式中において任意である。]
第二の合成方法としては、ジアルキルシロキサン鎖の両末端にハロゲン原子が結合した化合物(以下、「ジハロゲン化ジアルキルシロキサン」)と、トリス(トリアルキルシリルオキシ)シリル基と、M1O-基(M1は、アルカリ金属を表す。)が結合した化合物(以下、「アルカリ金属シリルオキシド」)及びケイ素原子に加水分解性基が4つ結合した化合物を反応させることにより製造することができる。これらの化合物の反応順序は限定されないが、まずジハロゲン化ジアルキルシロキサンとアルカリ金属シリルオキシドを反応させ、次いで、ケイ素原子に加水分解性基が4つ結合した化合物を反応させることが好ましい。
前記ハロゲン原子としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子等が挙げられ、塩素原子が好ましい。また、前記アルカリ金属としては、リチウムが好ましい。
アルカリ金属シリルオキシドは、例えば、トリス(トリアルキルシリルオキシ)シリル基とヒドロキシ基が結合した化合物に、アルキルアルカリ金属を反応させることにより製造することができる。有機アルカリ金属化合物としては、n-ブチルリチウム、sec-ブチルリチウム、tert-ブチルリチウム等のアルキルリチウムが挙げられ、特に好ましくはn-ブチルリチウムである。
金属化合物(b)の中心金属原子としては、具体的には、Al、Fe、In等の3価金属;Hf、Si、Ti、Sn、Zr等の4価金属;Ta等の5価金属;等が挙げられ、3価金属、4価金属が好ましく、より好ましくはAl、Fe、In等の3価金属;Hf、Si、Ti、Sn、Zr等の4価金属;であり、さらに好ましくはAl、Si、Ti、Zrであり、特に好ましくはSiである。
金属化合物(b)において、加水分解性基の個数は1以上であることが好ましく、より好ましくは2以上、さらに好ましくは3以上であり、4以下であることが好ましい。
Xは、それぞれ独立して、加水分解性基、炭素数1~12の含フッ素アルキル基又は炭素数1~4のアルキル基を表す。]
また、有機ケイ素化合物(a)と、金属化合物(b)の加水分解性基は同一の基であってもよく、いずれも炭素数1~4のアルコキシ基であることがより好ましい。
加水分解性基のみを有する化合物としては、テトラメトキシシラン、テトラエトキシシラン、テトラプロポキシシラン、テトラブトキシシラン等のテトラアルコキシシラン;トリエトキシアルミニウム、トリプロポキシアルミニウム、トリブトキシアルミニウム等のトリアルコキシアルミニウム;トリエトキシ鉄等のトリアルコキシ鉄;トリメトキシインジウム、トリエトキシインジウム、トリプロポキシインジウム、トリブトキシインジウム等のトリアルコキシインジウム;テトラメトキシハフニウム、テトラエトキシハフニウム、テトラプロポキシハフニウム、テトラブトキシハフニウム等のテトラアルコキシハフニウム;テトラメトキシチタン、テトラエトキシチタン、テトラプロポキシチタン、テトラブトキシチタン等のテトラアルコキシチタン;テトラメトキシスズ、テトラエトキシスズ、テトラプロポキシスズ、テトラブトキシスズ等のテトラアルコキシスズ;テトラメトキシジルコニウム、テトラエトキシジルコニウム、テトラプロポキシジルコニウム、テトラブトキシジルコニウム等のテトラアルコキシジルコニウム;ペンタメトキシタンタル、ペンタエトキシタンタル、ペンタプロポキシタンタル、ペンタブトキシタンタル等のペンタアルコキシタンタル;等が挙げられる。
2個のシロキサン骨格含有基と加水分解性基を有する化合物としては、ジ(トリメチルシリルオキシ)ジメトキシシラン、ジ(トリメチルシリルオキシ)ジエトキシシラン、ジ(トリメチルシリルオキシ)ジプロポキシシラン等のジ(トリメチルシリルオキシ)ジアルコキシシラン;等が挙げられる。
2個の炭化水素鎖含有基と加水分解性基を有する化合物としては、ジメチルジメトキシシラン、ジエチルジメトキシシラン、ジメチルジエトキシシラン、ジエチルジエトキシシラン等のジアルキルジアルコキシシラン;等が挙げられる。
更に、CF3(CF2)r8-(CH2)r9SiCH3Cl2、CF3(CF2)r8-(CH2)r9SiCH3(OCH3)2、CF3(CF2)r8-(CH2)r9SiCH3(OC2H5)2が挙げられる(r8はいずれも2~10であり、好ましくは3~7であり、r9はいずれも1~5であり、好ましくは2~4である)。
H2CF3))4-OCH3などが挙げられる。
前記アルコール系溶剤としては、メタノール、エタノール、プロパノール、イソプロピルアルコール、ブタノール、エチレングリコール、プロピレングリコール、ジエチレングリコール等が挙げられ、前記エーテル系溶剤としては、ジメトキシエタン、テトラヒドロフラン、ジオキサン等が挙げられ、ケトン系溶剤としては、アセトン、メチルエチルケトン等が挙げられ、エステル系溶剤としては、酢酸エチル、酢酸ブチル等が挙げられ、アミド系溶剤としては、ジメチルホルムアミド等が挙げられる。
中でも、アルコール系溶剤、ケトン系溶剤が好ましく、水を含んでいてもよい。
中でも、触媒(d)としては、有機金属化合物、酸性化合物が好ましく、有機アルミニウム化合物、塩酸がより好ましい。
また、触媒として酸性化合物を用いる場合、触媒(d)は、有機ケイ素化合物(a)と金属化合物(b)の合計100質量部に対して、0.001質量部以上であることが好ましく、より好ましくは0.005質量部以上、さらに好ましくは0.01質量部以上であり、1質量部以下であることが好ましく、より好ましくは0.5質量部以下である。
さらに、触媒として有機金属化合物を用いる場合、触媒(d)は、有機ケイ素化合物(a)と金属化合物(b)の合計100質量部に対して、0.0001質量部以上であることが好ましく、より好ましくは0.0002質量部以上、さらに好ましくは0.001質量部以上であり、0.1質量部以下であることが好ましく、より好ましくは0.05質量部以下である。
前記基材には、予め易接着処理を施しておいてもよい。易接着処理としては、コロナ処理、プラズマ処理、紫外線処理等の親水化処理が挙げられる。また、樹脂、シランカップリング剤、テトラアルコキシシラン等によるプライマー処理を用いてもよい。プライマー処理によりプライマー層を撥水膜と基体の間に設けることで、耐湿性や耐アルカリ性等の耐久性をより向上できる。
プライマー層としては、例えば、下記式(III)で表される化合物および/またはその部分加水分解縮合物からなる(P1)成分を含む下地層形成用組成物を用いて形成された層が好ましい。
[ただし、式(III)中、XP2はそれぞれ独立して、ハロゲン原子、アルコキシ基またはイソシアネート基を示す。]
[ただし、式(IV)中、XP3はそれぞれ独立して加水分解性基または水酸基を示し、pは1~8の整数である。]
本発明の実施例で用いた測定法は下記の通りである。
協和界面化学社製「DM700」を使用し、液量を3μLとして、θ/2法にて透明皮膜表面の水に対する接触角を測定した。
耐光試験後の接触角変化率が-27%以上であるか、耐熱試験後の接触角変化率が-15%以上である場合を○、これらの条件を満たさない場合を×として評価した。
消しゴム付きHB鉛筆(三菱鉛筆社)を具備した、スチールウール試験機(大栄精機社製)を用いた。消しゴムが透明皮膜に接した状態で、荷重500gをかけて摩耗試験を行い、初期接触角から-15°以下となるまでの回数を測定した。
透明皮膜表面に3μLの液滴を乗せ、水平から90°まで傾けた際の液滴の滑り具合を、滑落スピードの官能評価にて評価した。評価基準は下記の通りとした。
◎:非常によく滑る、○:滑る、△:引っかかりを感じる、×:滑らない
透明皮膜表面を指でこすり、触感、指の滑り性を官能評価にて評価した。評価基準は下記の通りとした。
◎:非常によく滑る、○:滑る、△:引っかかりを感じる、×:滑らない
オルトケイ酸テトラエチル(テトラエトキシシラン)13.4gに、水酸化ナトリウム0.86gを添加し、室温で2時間撹拌した。得られた溶液をドライアイスで-40℃に冷却しながら、ヘプタンで0.4倍に希釈した下記式
三つ口フラスコに、トリメチルシラノール4.8g、テトラヒドロフラン(THF)56mLを仕込み、窒素置換した。-40℃に冷却し、n-ブチルリチウム(n-BuLi)ヘキサン溶液(1.6mol/L)を33.6mL滴下した。15分撹拌して室温に戻して前駆体溶液を得た。三ツ口フラスコに、1,7-ジクロロオクタメチルテトラシロキサン20gとTHF80mLを仕込み、-30℃まで冷却して、前駆体溶液を滴下した。2時間撹拌した後、140hPa、30℃で濃縮したのち、ヘキサンで洗浄した。6hPa、74.9℃~82.4℃で蒸留して、蒸留物(前駆体2)を回収した。
コンデンサーを装着した三ツ口フラスコに、トリクロロイソシアヌル酸3.94gを仕込み、窒素置換を実施した。セプタムよりジクロロメタン50mLを仕込み、撹拌、トリス(トリメチルシロキシ)シラン5.0gを加えた。1時間撹拌した後、ろ過した。濾液をジエチルエーテル150mL、イオン交換水50mL、トリエチルアミン1.87gを仕込んだ氷バスで冷却しながら、濾液を滴下した。室温で1時間撹拌した。イオン交換水で洗浄し、硫酸マグネシウムで脱水して、150mmHg、25℃で濃縮し、目的の中間体3(シラノール1)を5.8g得た。
合成例3と同様にして、中間体3(シラノール1)を得た。次いで、三ツ口フラスコに、中間体3(シラノール1)を1.88g、THFを5.04g仕込み、撹拌した。-40℃に冷却し、n-BuLiヘキサン溶液(1.6mol/L)を3.75mL滴下した。0℃まで昇温し、12.32gのTHFに溶解したヘキサメチルシクロトリシロキサン10.68gを滴下し、17時間撹拌した。-40℃に冷却し、THF5.33gに溶解させたクロロトリエトキシシラン1.19gを滴下した。ヘキサン150mLを加えて濾過した。濾液を130hPa、25℃で濃縮し、下記式で表される化合物4を13.11g得た。
得られた化合物4の1H-NMR(400MHz,基準:CHCl3 (=7.24ppm))の測定結果を以下に示す。
溶剤(c)としてのメチルエチルケトン3.88mL(3.12g)に、上記有機ケイ素化合物(a)としての化合物1を2.5×10-4モル(0.14g)、金属化合物(b)としてのオルトケイ酸テトラエチル(テトラエトキシシラン)を5×10-3モル(1.04g)、触媒(d)としてのエチルアセトアセテートアルミニウムジイソプロピレートの25%イソプロピルアルコール溶液(川研ファインケミカル社製「ALCH-75」を3倍希釈したもの)を200μL加え、24時間撹拌して試料溶液1を作製した。
溶剤(c)、有機ケイ素化合物(a)、金属化合物(b)、触媒(d)を表1に示す通りにしたこと以外は実施例1と同様にして、試料溶液2~4を作製した。
オクチルトリエトキシシラン0.5mL、オルトケイ酸テトラエチル7.05mL、0.01M塩酸9.5mL、エタノール17mLを混合した。得られた混合液をエタノールで8倍希釈し、比較試料溶液1とした。
オプツールDSX-E(ダイキン社製)0.2gとNovec7200(3M社製)39.8gを室温で撹拌して、比較塗布溶液2を得た。
アルカリ洗浄したガラス基板(Corning社製「EAGLE XG」)に、試料溶液1、3、4、又は比較試料溶液1を3000rpm、20秒の条件でスピンコーター(MIKASA社製)を用いてスピンコートし、これを1日室温で静置した後、さらに120℃で硬化させ、本発明の透明皮膜、又は比較例の皮膜を得た。
得られた皮膜の接触角、耐摩耗性、液滴の滑り性、触感・指の滑り性を表1に示す。
試料溶液2、3を、それぞれメチルエチルケトンで30倍に希釈し、塗布溶液2、3とした。また、試料溶液4をメチルエチルケトンで20倍に希釈し、塗布溶液4とした。
アルカリ洗浄したガラス基板(Corning社製「EAGLE XG」)に、塗布溶液2~4、又は比較塗布溶液2を3000rpm、20秒の条件でスピンコーター(MIKASA社製)を用いてスピンコートし、これを1日室温で静置した後、さらに120℃で硬化させ、本発明の透明皮膜、又は比較例の皮膜を得た。
なお、上記水銀ランプ(ウシオ電機社製「SP-9 250DB」)の分光放射照度は図1に示す通りであり、波長300nm以下の領域に輝線を有していた。
接触角変化率(%)={(BZ-A1)/A1}×100(%)
Claims (14)
- ポリシロキサン骨格と、
前記ポリシロキサン骨格を形成するケイ素原子のうち一部のケイ素原子に結合するトリアルキルシリル基含有分子鎖とを含む透明被膜であって、
前記トリアルキルシリル基含有分子鎖中のアルキル基がフルオロアルキル基に置き換わっていてもよく、
透明皮膜上の液滴の初期接触角をA0、温度200℃で24時間静置した後の接触角を
BH、強度250Wのキセノンランプを100時間照射した後の接触角をBLとしたときに、
(BH-A0)/A0×100(%)≧-27(%)、および、
(BL-A0)/A0×100(%)≧-15(%)
の少なくとも一方を満足する透明皮膜。 - ポリシロキサン骨格と、
前記ポリシロキサン骨格を形成するケイ素原子のうち一部のケイ素原子に結合するトリアルキルシリル基含有分子鎖とを含む透明被膜であって、
前記トリアルキルシリル基含有分子鎖中のアルキル基がフルオロアルキル基に置き換わっていてもよく、
透明被膜上の液滴の初期接触角をA1、300nm以下の領域に輝線を有する水銀ランプの光を照射面における強度を200±10mW/cm2として、温度20~40℃、湿度30~75%の大気雰囲気下で、4時間照射した後の透明皮膜上の液滴の接触角をBz1としたときに、下記式で表される関係を満足する透明皮膜。
(Bz1-A1)/A1×100(%)≧-9(%) - 金属アルコキシドを形成しうる3価又は4価の金属原子から選ばれる金属原子と、前記トリアルキルシリル基含有分子鎖の分子鎖を構成する元素数よりも少ない元素数のシロキサン骨格含有基、およびヒドロキシ基よりなる群から選ばれる基であって、前記金属原子に結合する基とから構成されるユニットを有し、このユニットが金属原子の部位で前記ポリシロキサン骨格に結合している請求項1~4のいずれかに記載の透明皮膜。
- MがAl、Si、Ti又はZrである請求項6に記載の透明皮膜。
- MがSiである請求項7に記載の透明皮膜。
- 前記構造(B)と、トリアルキルシリル基含有分子鎖がケイ素原子に結合している構造(A)の存在比(構造(B)/構造(A))が、モル基準で0.1以上、80以下である請求項6~8のいずれかに記載の透明皮膜。
- 透明皮膜上の液滴の初期接触角が、95°以上である請求項1~9のいずれかに記載の透明皮膜。
- 少なくとも1つのトリアルキルシリル基含有分子鎖と、少なくとも1つの加水分解性基とがケイ素原子に結合している有機ケイ素化合物(a)、及び加水分解性基が金属原子に結合している金属化合物(b)を含むコーティング組成物。
- 前記金属化合物(b)が下記式(II-1)で表される化合物及びその加水分解縮合物からなる群より選ばれる少なくとも1種であって、金属化合物(b)と有機ケイ素化合物(a)のモル比(金属化合物(b)/有機ケイ素化合物(a))が10以上である請求項11に記載のコーティング組成物。
[式(II-1)中、Mは金属アルコキシドを形成しうる3価又は4価の金属原子を表す。
Ab1は、それぞれ独立に、加水分解性基を表す。
Rb2は、シロキサン骨格含有基、炭化水素鎖含有基又は加水分解性基を表し、Rb2およびZb2がシロキサン骨格含有基又は炭化水素鎖含有基の場合、Rb2とZb2とは同一であっても異なっていてもよく、Zb2が加水分解性基の場合、Rb2とAb1とは同一でも異なっていてもよい。また、複数の式(II-1)間でRb2とZb2は同一であっても異なっていてもよい。
またRb2がシロキサン骨格含有基の場合、シロキサン骨格含有基は、有機ケイ素化合物(a)のトリアルキルシリル基含有分子鎖を構成する元素数よりも少ない元素数からなる。
Zb2は、シロキサン骨格含有基、炭化水素鎖含有基又は加水分解性基を表す。
kは、Mに応じて、0又は1の整数を表す。] - 前記有機ケイ素化合物(a)が下記式(I-I)で表される化合物である請求項11に記載のコーティング組成物。
[式(I-I)中、Aa1は、それぞれ独立に、加水分解性基を表す。
Za2は、トリアルキルシリル基含有分子鎖、炭化水素鎖含有基、シロキサン骨格含有基又は加水分解性基を表し、Za2が加水分解性基の場合、Za2とAa1とは、同一であっても異なっていてもよい。また、複数の式(I-I)間でRaとZa2とは同一であっても異なっていてもよい。
Rs3は、それぞれ独立に、炭素数1以上、4以下のアルキル基を表す。
Rs4は、炭素数1以上、10以下の2価の炭化水素基を表し、Rs4中のメチレン基(-CH2-)は、酸素原子で置き換わっていてもよい。
Rs5は、それぞれ独立に、炭素数1以上、4以下のアルキル基を表す。
m1、n1は、それぞれ独立に、0以上の整数を表す。
ただし添字n1、m1を付して括弧でくくられた各繰り返し単位の存在順序は、式中において任意である。] - 下記式(I-I)で表される化合物。
[式(I-I)中、Aa1は、それぞれ独立に、加水分解性基を表す。
Za2は、トリアルキルシリル基含有分子鎖、炭化水素鎖含有基、シロキサン骨格含有基又は加水分解性基を表し、Za2が加水分解性基の場合、Za2とAa1とは、同一であっても異なっていてもよい。また、複数の式(I-I)間でRaとZa2とは同一であっても異なっていてもよい。
Rs3は、それぞれ独立に、炭素数1以上、4以下のアルキル基を表す。
Rs4は、炭素数1以上、10以下の2価の炭化水素基を表し、Rs4中のメチレン基(-CH2-)は、酸素原子で置き換わっていてもよい。
Rs5は、それぞれ独立に、炭素数1以上、4以下のアルキル基を表す。
m1、n1は、それぞれ独立に、0以上の整数を表す。
ただし添字n1、m1を付して括弧でくくられた各繰り返し単位の存在順序は、式中において任意である。]
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CN107109124B (zh) | 2021-07-09 |
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CN107109124A (zh) | 2017-08-29 |
JPWO2016068138A1 (ja) | 2017-09-07 |
JP6704854B2 (ja) | 2020-06-03 |
KR102441644B1 (ko) | 2022-09-07 |
KR20170078708A (ko) | 2017-07-07 |
US10472378B2 (en) | 2019-11-12 |
US20170313728A1 (en) | 2017-11-02 |
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