WO2016199908A1 - 表面処理剤 - Google Patents
表面処理剤 Download PDFInfo
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- WO2016199908A1 WO2016199908A1 PCT/JP2016/067418 JP2016067418W WO2016199908A1 WO 2016199908 A1 WO2016199908 A1 WO 2016199908A1 JP 2016067418 W JP2016067418 W JP 2016067418W WO 2016199908 A1 WO2016199908 A1 WO 2016199908A1
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- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000005355 lead glass Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000005304 optical glass Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
-
- 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
- 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
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/71—Monoisocyanates or monoisothiocyanates
- C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/83—Chemically modified polymers
- C08G18/837—Chemically modified polymers by silicon containing compounds
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/11—Anti-reflection coatings
- G02B1/113—Anti-reflection coatings using inorganic layer materials only
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/12—Optical coatings produced by application to, or surface treatment of, optical elements by surface treatment, e.g. by irradiation
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/18—Coatings for keeping optical surfaces clean, e.g. hydrophobic or photo-catalytic films
-
- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
Definitions
- the present invention relates to a (poly) ether group-containing silane compound and a surface treatment agent comprising the same.
- silane compounds can provide excellent functions (for example, water repellency, oil repellency, and antifouling properties) when used for surface treatment of a substrate.
- a layer obtained from a surface treatment agent containing a silane compound (hereinafter also referred to as “surface treatment layer”) is applied as a so-called functional thin film to various substrates such as glass, plastic, fiber, and building materials. .
- Fluorine-containing silane compounds are known as such silane compounds.
- Patent Documents 1 and 2 describe perfluoropolyether group-containing silane compounds having hydrolyzable groups bonded to Si atoms at the molecular ends.
- Patent Documents 3 and 4 describe polyether group-containing silane compounds having hydrolyzable groups bonded to Si atoms at the molecular ends.
- the surface treatment layer obtained from the surface treatment agent as described in Patent Documents 1 to 4 can exhibit the above-described functions even in a thin film, the optical properties such as glasses and touch panels that require light transmission or transparency are required. It is suitably used for members. In such applications, fingerprint adhesion can be a problem.
- a layer obtained from a surface treatment agent containing a perfluoropolyether group-containing silane compound as described in Patent Documents 1 and 2 has excellent water and oil repellency, and fingerprints are difficult to adhere.
- the amount of fingerprint adhesion is small, but when a fingerprint adheres, its excellent water and oil repellency, that is, high contact angle. For this reason, there is a problem that the attached sebum scatters light and the fingerprint becomes conspicuous.
- the layer obtained from the surface treatment agent containing the polyether-containing silane compound as described in Patent Documents 1 and 2 has high lipophilicity, and the attached sebum conforms to the layer, so that even when fingerprints are attached, the layer is conspicuous. Absent.
- the layer obtained from the surface treatment agent containing the polyether-containing silane compound as described in Patent Documents 1 and 2 has a problem that the friction durability is low and the function cannot be maintained for a long time.
- An object of the present invention is to provide a silane compound capable of forming a layer having low visibility of attached fingerprints and excellent friction durability, and a surface treatment agent containing the silane compound.
- R 1 represents OR 4 ;
- R 4 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms;
- PE 1 has the formula: -(C a H 2a O) b- (Where: a is an integer from 1 to 6 independently for each unit in parentheses with b appended; b is an integer of 1 to 200 independently at each occurrence.
- a group represented by: Y represents a single bond or —CONH—R 5 —NHCOO— independently at each occurrence; R 5 represents, independently at each occurrence, a divalent organic group; n is an integer from 1 to 50; PE 2 represents a single bond or the aforementioned — (C a H 2a O) b — group; Each X independently represents a single bond or a di- to 10-valent organic group; R a independently represents —Z—SiR 71 p R 72 q R 73 r at each occurrence; Z represents, independently at each occurrence, an oxygen atom or a divalent organic group; R 71 independently represents R a ′ at each occurrence; R a ′ is synonymous with R a ; In R a , the maximum number of Si linearly linked via the Z group is 5; R 72 independently represents at each occurrence a hydroxyl group or a hydrolyzable group; R 73 independently represents at each occurrence a hydrogen atom or a lower alkyl group
- a surface treating agent containing at least one compound represented by the above formula (A1) or formula (A2).
- an article including a base material and a layer formed of the surface treatment agent on the surface of the base material.
- a novel (poly) ether group-containing silane compound and a surface treating agent comprising the same are provided.
- a surface treatment agent even when fingerprints are attached, a surface treatment layer having low fingerprint visibility and excellent friction durability can be formed.
- hydrocarbon group means a group containing carbon and hydrogen, and a group in which one hydrogen atom has been eliminated from a hydrocarbon.
- Such hydrocarbon group is not particularly limited, but may be a hydrocarbon group having 1 to 20 carbon atoms which may be substituted by one or more substituents, such as an aliphatic hydrocarbon group, An aromatic hydrocarbon group etc. are mentioned.
- the “aliphatic hydrocarbon group” may be linear, branched or cyclic, and may be either saturated or unsaturated.
- the hydrocarbon group may also contain one or more ring structures.
- Such a hydrocarbon group may have one or more N, O, S, Si, amide, sulfonyl, siloxane, carbonyl, carbonyloxy and the like at its terminal or molecular chain.
- the substituent of the “hydrocarbon group” is not particularly limited, but includes, for example, a halogen atom; C 1-6 alkyl optionally substituted by one or more halogen atoms Group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 3-10 cycloalkyl group, C 3-10 unsaturated cycloalkyl group, 5-10 membered heterocyclyl group, 5-10 membered unsaturated heterocyclyl And one or more groups selected from a group, a C 6-10 aryl group and a 5-10 membered heteroaryl group.
- divalent to decavalent organic group means a divalent to decavalent group containing carbon.
- a divalent to decavalent organic group is not particularly limited, and examples thereof include divalent to decavalent groups in which 1 to 9 hydrogen atoms are further eliminated from a hydrocarbon group.
- the divalent organic group is not particularly limited, and examples thereof include a divalent group in which one hydrogen atom is further eliminated from a hydrocarbon group.
- the present invention relates to the following general formula (A1) or (A2): At least one (poly) ether group-containing silane compound represented by the formula:
- R 1 represents OR 4 .
- R 4 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.
- the alkyl group having 1 to 20 carbon atoms may be linear or branched, and is preferably linear.
- the alkyl group having 1 to 20 carbon atoms is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms.
- the alkyl group having 1 to 20 carbon atoms is preferably a methyl group, an ethyl group or an n-propyl group, more preferably a methyl group.
- R 4 is preferably a hydrogen atom or a methyl group, more preferably a hydrogen atom.
- PE 1 independently represents each of the following formulas at each occurrence: -(C a H 2a O) b- (Where: a is independently an integer of 1 to 6, preferably an integer of 2 to 4 for each unit in parentheses with b appended; In each occurrence, b is independently an integer of 1 to 200, preferably an integer of 5 to 200, more preferably an integer of 5 to 100, and further preferably an integer of 5 to 50. ) It is group represented by these.
- each PE 2 independently represents a single bond or the following formula: -(C a H 2a O) b- (Wherein, a and b are as defined above.) It is group represented by these.
- — (C a H 2a O) b — in PE 1 and PE 2 is independently at each occurrence, -(C 4 H 8 O) c- (C 3 H 6 O) d- (C 2 H 4 O) e- (Where: c, d and e each independently represent an integer of 0 to 200, for example, an integer of 1 to 200, preferably an integer of 5 to 200, more preferably an integer of 5 to 100, and still more preferably 5 to An integer of 50; the sum of c, d and e is 1 to 200, preferably 5 to 200, more preferably 5 to 100, even more preferably 5 to 50; The order of presence of each repeating unit with the subscript c, d or e and enclosed in parentheses is arbitrary in the formula. ) It is group represented by these.
- a is 4 in at least one of the — (C a H 2a O) — units. That is, the formula (A1) or (A2) contains at least one —C 4 H 8 O— group. Such —C 4 H 8 O— group is preferably linear. By containing the —C 4 H 8 O— group, the compound of the present invention can provide a surface treatment layer that has low fingerprint visibility and can easily erase the trace of the fingerprint.
- the ratio of the number of (C 4 H 8 O) units, the number of (C 3 H 6 O) units, and the number of (C 2 H 4 O) units is not particularly limited.
- the number of (C 3 H 6 O) units and the number of (C 2 H 4 O) units are each 100% or less of the number of (C 4 H 8 O) units, preferably 80% or less, more preferably It may be 50% or less, more preferably 30% or less.
- — (C a H 2a O) b — in PE 1 and PE 2 is each independently at each occurrence - (C 4 H 8 O) c - (C 3 H 6 O) d -
- c and d are each independently an integer of 0 to 200, for example, an integer of 1 to 200, preferably an integer of 5 to 200, more preferably an integer of 5 to 100, and further preferably 5 to 50, at each occurrence.
- An integer; the sum of c and d is 1 to 200, preferably 5 to 200, more preferably 5 to 100, even more preferably 5 to 50;
- the order of existence of each repeating unit with the subscript c or d and enclosed in parentheses is arbitrary in the formula. ) It is group represented by these.
- the ratio between the number of (C 4 H 8 O) units and the number of (C 3 H 6 O) units is not particularly limited.
- the number of (C 3 H 6 O) units is 100% or less of the number of (C 4 H 8 O) units, preferably 80% or less, more preferably 50% or less, and even more preferably 30% or less. obtain.
- PE 1 and PE 2 are each independently at each occurrence, -(C 4 H 8 O) c- -(C 3 H 6 O) d- , and-(C 2 H 4 O) e- (Wherein c, d and e are each independently an integer of 1 to 200, preferably an integer of 5 to 200, more preferably an integer of 5 to 100, still more preferably an integer of 5 to 50). ) Is a group selected from That is, in this embodiment, PE 1 and PE 2 are each independently-(C 4 H 8 O) c -,-(C 3 H 6 O) d- , or-(C 2 H 4 O) e.
- At least one — (C 4 H 8 O) c -homopolymer unit is present in formula (A1) or (A2).
- - (C 4 H 8 O) c - in addition to the homopolymer units, there may be other two, only the other one may be present .
- the abundance ratio of each homopolymer unit is not particularly limited, but preferably the number of — (C 3 H 6 O) d -homopolymer units and — (C 2 H 4 O) e -homopolymer units
- the numbers may be 80% or less, preferably 50% or less, more preferably 30% or less, respectively, of the number of — (C 4 H 8 O) c -homopolymer units.
- PE 1 and PE 2 are each independently at each occurrence, -(C 4 H 8 O) c- , and-(C 3 H 6 O) d- (Wherein c and d are each independently an integer of 1 to 200, preferably an integer of 5 to 200, more preferably an integer of 5 to 100, still more preferably an integer of 5 to 50). Is a group selected from In a preferred embodiment, in formula (A1) or (A2), at least one — (C 4 H 8 O) c -homopolymer unit is included.
- the abundance ratio of each homopolymer unit is not particularly limited, but preferably the number of — (C 3 H 6 O) d -homopolymer units is — (C 4 H 8 O) c -homopolymer It may be 80% or less of the number of units, preferably 50% or less, more preferably 30% or less.
- PE 1 and PE 2 are each independently at each occurrence the formula: -(C 4 H 8 O) c- (Wherein c is an integer of 1 to 200, preferably an integer of 5 to 200, more preferably an integer of 5 to 100, still more preferably an integer of 5 to 50) It is group represented by these. That is, in this embodiment, PE 1 and PE 2 consist only of —C 4 H 8 O— units.
- — (C 4 H 8 O) — represents — (CH 2 CH 2 CH 2 CH 2 O) —, — (CH (CH 3 ) CH 2 CH 2 O) —, — (CH 2 CH (CH 3 ) CH 2 O) —, — (CH 2 CH 2 CH (CH 3 ) O) —, — (C (CH 3 ) 2 CH 2 O) —, — (CH 2 C (CH 3 ) 2 O)-,-(CH (CH 3 ) CH (CH 3 ) O)-,-(CH (C 2 H 5 ) CH 2 O)-and-(CH 2 CH (C 2 H 5 ) O ) — May be used, but — (CH 2 CH 2 CH 2 CH 2 O) — is preferred.
- — (C 3 H 6 O) — is any one of — (CH 2 CH 2 CH 2 O) —, — (CH (CH 3 ) CH 2 O) — and — (CH 2 CH (CH 3 ) O) —.
- — (CH 2 CH (CH 3 ) O) — is preferable.
- — (C 2 H 4 O) — may be either — (CH 2 CH 2 O) — or — (CH (CH 3 ) O) —, but preferably — (CH 2 CH 2 O)-.
- Y independently represents a single bond or —CONH—R 5 —NHCOO— at each occurrence.
- R 5 represents a divalent organic group independently at each occurrence.
- R 5 is preferably a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms or a divalent aromatic hydrocarbon group having 3 to 20 carbon atoms, which may have a substituent, or these It can be a combination.
- the aliphatic hydrocarbon group may be linear, branched or cyclic.
- R 5 is an optionally substituted alkylene having 1 to 20 carbon atoms, cycloalkylene having 3 to 20 carbon atoms, or arylene having 3 to 20 carbon atoms, or a combination thereof. possible.
- Preferred examples of the substituent include alkyl groups having 1 to 6 carbon atoms.
- R 5 can be a group represented by the following formula: -(CH 2 ) x ' -(wherein x' is an integer of 1 to 6, for example, an integer of 1 to 4); Wherein x and y are each independently an integer of 0-6, such as an integer of 0-3 or 1-3; z is an integer of 0 to 10, for example, 0 to 4 or an integer of 1 to 4. ) Wherein x and y are each independently an integer of 0-6, such as an integer of 0-3 or 1-3; z is an integer of 0 to 4, for example, 0 to 3 or an integer of 1 to 3. ) When x or y is 0, — (CH 2 ) x — or — (CH 2 ) y — means a single bond (bond).
- n is an integer of 1 to 50, preferably an integer of 1 to 30, for example, an integer of 5 to 30 or an integer of 10 to 20.
- each X independently represents a single bond or a divalent to 10-valent organic group.
- X is a polyether moiety (that is, R 1- (PE 1 -Y) n -PE 2 -part or-( PE 1 -Y) n -PE 2 - and parts), silane unit that provides a binding capability to a substrate (i.e., is understood as a linker for connecting the group) in parentheses are given the alpha. Therefore, X may be any organic group as long as the compounds represented by formulas (A1) and (A2) can exist stably.
- ⁇ is an integer from 1 to 9. These ⁇ may vary depending on the valence of X.
- ⁇ is a value obtained by subtracting 1 from the valence of X. For example, when X is a 10-valent organic group, ⁇ is 9, when X is a pentavalent organic group, ⁇ is 4, and when X is a divalent organic group, ⁇ is 1. It is.
- X is preferably 2 to 8 valent, for example 3 to 8 valent, more preferably 2 to 6 valent, for example 3 to 6 valent.
- X can be X 1a below.
- Examples of X 1a are not particularly limited, but for example, the following formula: -(R 30 ) r ' -[(R 31 ) p' -(X a ) q ' ]- [Where: R 30 is —CONH— or —CO—, preferably —CONH—; r ′ is 0 or 1, R 31 represents a single bond, — (CH 2 ) s ′ — or o-, m- or p-phenylene group, preferably — (CH 2 ) s ′ — s ′ is an integer of 1 to 20, preferably an integer of 1 to 6, more preferably an integer of 1 to 3, and even more preferably 1 or 2.
- X a represents-(X b ) l ' - X b is independently at each occurrence —O—, —S—, o—, m- or p-phenylene, —C (O) O—, —Si (R 33 ) 2 —, — ( Si (R 33 ) 2 O) m ′ —Si (R 33 ) 2 —, —CONR 34 —, —O—CONR 34 —, —NR 34 — and — (CH 2 ) n ′ —
- R 33 each independently represents a phenyl group, a C 1-6 alkyl group or a C 1-6 alkoxy group, preferably a phenyl group or a C 1-6 alkyl group, and more preferably a methyl group.
- R 34 each independently represents a hydrogen atom, a phenyl group or a C 1-6 alkyl group (preferably a methyl group) at each occurrence;
- m ′ is independently an integer of 1 to 100, preferably an integer of 1 to 20, at each occurrence,
- n ′ is independently an integer of 1 to 20, preferably an integer of 1 to 6, more preferably an integer of 1 to 3, at each occurrence.
- l ′ is an integer of 1 to 10, preferably an integer of 1 to 5, more preferably an integer of 1 to 3, p ′ is 0 or 1; q ′ is 0 or 1,
- at least one of p ′ and q ′ is 1, and in [(R 31 ) p ′ -(X a ) q ′ ], each repeating unit attached with p ′ or q ′ and enclosed in parentheses The order of existence is arbitrary]
- R 31 and X a (typically a hydrogen atom of R 31 and X a ) may be substituted with one or more substituents selected from C 1-3 alkyl groups.
- the X 1a is — (R 30 ) r ′ — (R 31 ) p ′ — (X a ) q ′ —R 32 —.
- R 32 represents a single bond, — (CH 2 ) t ′ — or o-, m- or p-phenylene group, and preferably — (CH 2 ) t ′ —.
- t ′ is an integer of 1 to 20, preferably an integer of 2 to 6, more preferably an integer of 2 to 3.
- R 32 (typically a hydrogen atom of R 32 ) may be substituted with one or more substituents selected from C 1-3 alkyl groups.
- X 1a is -R 30 -C 1-20 alkylene group, -R 30 -R 31 -X c -R 32- , -R 30 -X d -R 32- , A C 1-20 alkylene group, -R 31 -X c -R 32- , or -X d -R 32- [Wherein, R 30 , R 31 and R 32 have the same meaning as described above. ] It can be.
- the X 1a is -R 30 -C 1-20 alkylene group, -R 30- (CH 2 ) s' -X c- , —R 30 — (CH 2 ) s ′ —X c — (CH 2 ) t ′ — -R 30 -X d- , -R 30 -X d- (CH 2 ) t ' -, A C 1-20 alkylene group, -(CH 2 ) s' -X c- , -(CH 2 ) s ' -X c- (CH 2 ) t'- -X d- , or -X d- (CH 2 ) t ' - [Wherein, R 30 , s ′ and t ′ are as defined above] ] It is.
- X c is -O-, -S-, -C (O) O-, -CONR 34 -, -O-CONR 34 -, -Si (R 33 ) 2- , -(Si (R 33 ) 2 O) m ' -Si (R 33 ) 2- , —O— (CH 2 ) u ′ — (Si (R 33 ) 2 O) m ′ —Si (R 33 ) 2 —, —O— (CH 2 ) u ′ —Si (R 33 ) 2 —O—Si (R 33 ) 2 —CH 2 CH 2 —Si (R 33 ) 2 —O—Si (R 33 ) 2 —, —O— (CH 2 ) u ′ —Si (OCH 3 ) 2 OSi (OCH 3 ) 2 —, —CONR 34 — (CH 2 ) u ′ — (Si (Si (OC
- X d is -S-, -C (O) O-, -CONR 34 -, —CONR 34 — (CH 2 ) u ′ — (Si (R 33 ) 2 O) m ′ —Si (R 33 ) 2 —, —CONR 34 — (CH 2 ) u ′ —N (R 34 ) —, or —CONR 34 — (o-, m- or p-phenylene) -Si (R 33 ) 2 — [Wherein each symbol is as defined above. ] Represents.
- the X 1a is -R 30 -C 1-20 alkylene group, —R 30 — (CH 2 ) s ′ —X c — (CH 2 ) t ′ —, -R 30 -X d- (CH 2 ) t ' -, A C 1-20 alkylene group, — (CH 2 ) s ′ —X c — (CH 2 ) t ′ —, or —X d — (CH 2 ) t ′ — [Wherein each symbol is as defined above. ] It can be.
- said X 1a is -R 30 -C 1-20 alkylene group, —R 30 — (CH 2 ) s ′ —O— (CH 2 ) t ′ —, —R 30 — (CH 2 ) s ′ — (Si (R 33 ) 2 O) m ′ —Si (R 33 ) 2 — (CH 2 ) t ′ —, -R 30 - (CH 2) s '-O- (CH 2) u' - (Si (R 33) 2 O) m '-Si (R 33) 2 - (CH 2) t' -, -R 30 - (CH 2) s ' -O- (CH 2) t '-Si (R 33) 2 - (CH 2) u' -Si (R 33) 2 - (C v H 2v) -, A C 1-20 alkylene group, — (CH 2 ) s ′ —O— (CH 2
- — (C v H 2v ) — may be linear or branched.
- the X 1a group may be substituted with one or more substituents selected from C 1-3 alkyl groups.
- the X 1a group includes, for example, the following groups: [Wherein, each R 41 independently represents a hydrogen atom, a phenyl group, an alkyl group having 1 to 6 carbon atoms, or a C 1-6 alkoxy group, preferably a methyl group; D is —CH 2 O (CH 2 ) 2 —, —CH 2 O (CH 2 ) 3 —, -CF 2 O (CH 2) 3 -, -(CH 2 ) 2- , -(CH 2 ) 3- , - (CH 2) 4 -, -CONH- (CH 2 ) 2- , -CONH- (CH 2 ) 3- , -CONH- (CH 2) 4 -, -CO- (CH 2 ) 2- , -CO- (CH 2 ) 3- , -CO- (CH 2) 4 -, -CON (CH 3 )-(CH 2 ) 3- , —CON (Ph) — (CH 2 ) 3 — (where
- X 1a examples include, for example: -CONH- (CH 2 ) 2- , -CONH- (CH 2 ) 3- , -CONH- (CH 2) 4 -, -CO- (CH 2 ) 2- , -CO- (CH 2 ) 3- , -CO- (CH 2) 4 -, —CH 2 O (CH 2 ) 2 —, —CH 2 O (CH 2 ) 3 —, —CH 2 O (CH 2 ) 6 —, -CH 2 O (CH 2 ) 3 Si (CH 3 ) 2 OSi (CH 3 ) 2 (CH 2 ) 2- , -CH 2 O (CH 2) 3 Si (CH 3) 2 OSi (CH 3) 2 OSi (CH 3) 2 (CH 2) 2 -, -CH 2 O (CH 2 ) 3 Si (CH 3 ) 2 O (Si (CH 3 ) 2 O) 2 Si (CH 3 ) 2 (CH 2 ) 2- , —CH 2 O (CH 2 )
- X can be X 1b .
- X 1b groups include the following groups: [Where: Each of R 41 is independently a hydrogen atom, a phenyl group, an alkyl group having 1 to 6 carbon atoms, or a C 1-6 alkoxy group, preferably a methyl group; In each X 1 group, any some of T are bonded to PE 2 of the molecular backbone: —CH 2 O (CH 2 ) 2 —, —CH 2 O (CH 2 ) 3 —, -CF 2 O (CH 2) 3 -, -(CH 2 ) 2- , -(CH 2 ) 3- , - (CH 2) 4 -, -CONH- (CH 2 ) 2- , -CONH- (CH 2 ) 3- , -CONH- (CH 2) 4 -, -CO- (CH 2 ) 2- , -CO- (CH 2 ) 3- , -CO- (CH 2) 4 -, -CON (CH 2 ) 2-
- T (CH 2 ) n ′′ — (n ′′ is an integer of 2 to 6) bonded to the Si atom, and when present, the rest are each independently methyl A group, a phenyl group or a C 1-6 alkoxy group.
- X 1a can be a tri to 10 valent organic group.
- silane moiety is a binding site for a substrate (SiR a k R b l R c m) may be present two or more. By setting it as such a structure, the friction durability of a surface treatment layer can be improved.
- X can be X 2 below.
- X 2 represents —CONH—R 61 —R 62 (R 61 —NHCO—R 63 ) ⁇ -1
- R 61 independently represents a divalent hydrocarbon group
- R 62 represents a ⁇ -valent organic group
- ⁇ is an integer from 2 to 6
- R 63 represents —O—R 67 (OR 68 ) s (O—X 1a —) t
- R 67 represents a ⁇ -valent organic group
- ⁇ is an integer from 2 to 8
- R 68 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
- X 1a is a divalent organic group and has the same meaning as X 1a described above
- s is an integer from 0 to 6
- t is an integer from 1 to 7
- the sum of s and t is ⁇ -1.
- the R 61 are each independently preferably an alkylene group which has ⁇ 1 carbon atoms which may 10 have a substituent, an arylene group of a cycloalkylene group or 3 to 10 carbon atoms having 3 to 10 carbon atoms More preferably, it is an alkylene group having 1 to 10 carbon atoms which may have a substituent, for example, an alkylene group having 3 to 8 carbon atoms.
- R 62 is preferably an optionally substituted divalent to hexavalent aliphatic hydrocarbon group, alicyclic hydrocarbon group, aliphatic heterocyclic group, aromatic group or aromatic heterocyclic group.
- ⁇ is 3-6, ie R 62 is trivalent to hexavalent.
- silane moiety having a binding site hydrolyzable groups to a substrate may be present two or more. By setting it as such a structure, the friction durability of a surface treatment layer can be improved.
- the portion excluding R 63 ie, —CONH—R 61 —R 62 (R 61 —NHCO—) ⁇ -1
- R 63 ie, —CONH—R 61 —R 62 (R 61 —NHCO—) ⁇ -1
- R 63 ie, —CONH—R 61 —R 62 (R 61 —NHCO—) ⁇ -1
- R 63 ie, —CONH—R 61 —R 62 (R 61 —NHCO—) ⁇ -1
- R 63 ie, —CONH—R 61 —R 62 (R 61 —NHCO—) ⁇ -1
- R 67 is preferably an optionally substituted divalent to octavalent aliphatic hydrocarbon group, alicyclic hydrocarbon group, aliphatic heterocyclic group, aromatic group or aromatic heterocyclic group.
- ⁇ is 3-8, ie R 67 is 3-8 valent.
- silane moiety having a binding site hydrolyzable groups to a substrate may be present two or more. By setting it as such a structure, the friction durability of a surface treatment layer can be improved.
- R 63 the portion excluding X 1a (ie, —O—R 67 (OR 68 ) s (O—) t ) can be understood as a polyol residue, and has, for example, the following structure.
- R 68 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, such as a methyl group or an ethyl group, and is preferably a hydrogen atom.
- S is an integer of 0 to 6, preferably an integer of 0 to 3, more preferably 0 or 1, and still more preferably 0.
- X 2 is represented by the following formula: [Wherein, R 61 , R 67 , X 1 and t are as defined above. ] It is group represented by these.
- R 61 is preferably an optionally substituted alkylene group having 1 to 8 carbon atoms, a cycloalkylene group having 5 to 8 carbon atoms, or a phenylene group.
- the substituent is preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group or an ethyl group, and still more preferably a methyl group.
- R 67 can be a divalent to hexavalent hydrocarbon chain having 2 to 6 carbon atoms, preferably 2 to 4 valences, more preferably a divalent or trivalent carbon number 2 to 6.
- R 67 may be the following group: [In the formula, a bond marked with * is bonded to the isocyanurate ring side. ]
- X 1 may preferably be an alkylene group having 1 to 8 carbon atoms, more preferably an alkylene group having 2 to 6 carbon atoms.
- each X independently represents a trivalent to 10 valent organic group
- each ⁇ independently represents an integer of 2 to 9.
- all of the parenthesized units with ⁇ contain Si atoms to which hydroxyl groups or hydrolyzable groups are bound.
- R a independently represents —Z—SiR 71 p R 72 q R 73 r at each occurrence.
- Z represents an oxygen atom or a divalent organic group independently at each occurrence.
- Z is preferably a C 1-6 alkylene group, — (CH 2 ) g —O— (CH 2 ) h — (wherein g is an integer of 1 to 6, and h is 1 to 6 Or -phenylene- (CH 2 ) i- (wherein i is an integer of 0 to 6), more preferably a C 1-3 alkylene group.
- These groups may be substituted with, for example, one or more substituents selected from a fluorine atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, and a C 2-6 alkynyl group. .
- R 71 represents R a ′ independently at each occurrence.
- R a ′ has the same meaning as R a .
- Si is connected to the linear through the Z group is a five at the maximum. That is, in the above R a , when at least one R 71 is present, there are two or more Si atoms linearly linked via a Z group in R a , The maximum number of Si atoms connected in a chain is five.
- the "number of Si atoms linearly linked via a Z group in R a" is equal to -Z-Si- repeating number of which is connected to a linear during R a.
- * means a site bonded to Si of the main chain, and ... means that a predetermined group other than ZSi is bonded, that is, all three bonds of Si atoms are ... In this case, it means the end point of ZSi repetition.
- the number on the right shoulder of Si means the number of appearances of Si connected in a straight line through the Z group counted from *. That is, the chain in which ZSi repeat is completed in Si 2 has “the number of Si atoms linearly linked through the Z group in Ra ”, and similarly, Si 3 , Si 4 And the chain in which the ZSi repetition is completed in Si 5 has “number of Si atoms linearly linked through the Z group in R a ” being 3, 4 and 5, respectively.
- R a but ZSi chain there are multiple, they need not be all the same length, each may be of any length.
- the number of Si atoms connected linearly via the Z group in R a is one (left formula) or two (right formula) in all chains. Formula).
- the number of Si atoms connected in a straight chain via a Z group in R a is 1 or 2, preferably 1.
- R 72 independently represents a hydroxyl group or a hydrolyzable group at each occurrence.
- hydrolyzable group as used herein means a group capable of undergoing a hydrolysis reaction.
- hydrolyzable groups include —OR, —OCOR, —O—N ⁇ C (R) 2 , —N (R) 2 , —NHR, halogen (wherein R is substituted or unsubstituted Represents an alkyl group having 1 to 4 carbon atoms), preferably —OR (alkoxy group).
- R include unsubstituted alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, n-butyl group and isobutyl group; substituted alkyl groups such as chloromethyl group.
- an alkyl group particularly an unsubstituted alkyl group is preferable, and a methyl group or an ethyl group is more preferable.
- the hydroxyl group is not particularly limited, but may be a group produced by hydrolysis of a hydrolyzable group.
- R 72 is —OR (wherein R represents a substituted or unsubstituted C 1-3 alkyl group, more preferably a methyl group).
- R 73 independently represents a hydrogen atom or a lower alkyl group at each occurrence.
- the lower alkyl group is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and still more preferably a methyl group.
- '(if R a' is absent, R a) terminal of R a in R a in the above q is preferably 2 or more, for example 2 or 3, more preferably 3.
- R b represents a hydroxyl group or a hydrolyzable group independently at each occurrence.
- the “hydrolyzable group” has the same meaning as described for R 72 , and preferably —OR, —OCOR, —O—N ⁇ C (R) 2 , —N (R) 2 , —NHR , Halogen (in these formulas, R represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms), preferably —OR.
- R includes an unsubstituted alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, and an isobutyl group; and a substituted alkyl group such as a chloromethyl group.
- an alkyl group particularly an unsubstituted alkyl group is preferable, and a methyl group or an ethyl group is more preferable.
- the hydroxyl group is not particularly limited, but may be a group produced by hydrolysis of a hydrolyzable group. More preferably, R b is —OR (wherein R represents a substituted or unsubstituted C 1-3 alkyl group, more preferably a methyl group).
- R c independently represents a hydrogen atom or a lower alkyl group at each occurrence.
- the lower alkyl group is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and still more preferably a methyl group.
- k is 1 to 3, more preferably 2 or 3, even more preferably 3.
- R a is present.
- k is 1 to 3, more preferably 2 or 3, and still more preferably 3.
- the unit in parentheses with ⁇ includes two or more Si atoms to which a hydroxyl group or a hydrolyzable group is bonded.
- the number average molecular weight of the (poly) ether group-containing silane compound of the present invention is preferably 200 or more, more preferably 500 or more, preferably 10,000 or less, more preferably 5,000 or less, and still more preferably 2, 000 or less.
- the number average molecular weight of the polyether part (PE 1 group) in the (poly) ether group-containing silane compound of the present invention is not particularly limited, but is preferably 200 or more, more preferably 500 or more, preferably It can be 10,000 or less, more preferably 5,000 or less, and even more preferably 2,000 or less.
- PE 1 has such a number average molecular weight, the visibility of the fingerprint attached to the substrate is lowered, and the fingerprint visibility can be easily lowered by wiping the attached fingerprint.
- the “number average molecular weight” is measured by GPC (gel permeation chromatography) analysis.
- the (poly) ether group-containing silane compound of the present invention preferably has a glass transition temperature (Tg) of ⁇ 70 ° C. or higher, preferably 40 ° C. or lower, more preferably 30 ° C. or lower, and even more preferably 20 ° C. or lower. Can do.
- Tg glass transition temperature
- the “glass transition temperature” is measured by differential scanning calorimetry.
- At least one terminal of the polyether group may have two or more silane sites having a hydroxyl group or a hydrolyzable group that is a binding site to the base material. Therefore, it can be strongly bonded to the base material, and it is considered that high friction durability can be achieved.
- the (poly) ether group-containing silane compound represented by the formula (A1) and the formula (A2) can be produced by a known method.
- a polyether group-containing dialcohol corresponding to PE 1 and PE 2 and a diisocyanate group corresponding to Y are reacted to synthesize R 1- (PE 1 -Y) n -PE 2 -H, R 1 - and OH groups at the end of (PE 1 -Y) n -PE 2 -H, by reacting the -X-SiR a k R b l silane compound having an isocyanate group that corresponds to R c m at the end Obtainable.
- reaction conditions for producing the (poly) ether group-containing silane compound of the present invention can be appropriately adjusted to a preferable range by those skilled in the art.
- the surface treating agent of the present invention contains at least one (poly) ether group-containing silane compound represented by any one of formula (A1) and formula (A2).
- the surface treatment agent of the present invention is not particularly limited, but can impart hydrophilicity, lipophilicity, antifouling property, surface slipperiness, wiping property, friction durability, etc. to the substrate depending on the structure. .
- the surface treatment layer formed on the base material using the surface treatment agent containing the compound of the present invention has high lipophilicity. That is, the surface treating agent containing the compound of the present invention has a contact angle with respect to n-hexadecane of preferably 40 ° or less, more preferably 30 ° or less, still more preferably 25 ° or less, and preferably 10 ° or more. More preferably, a surface treatment layer of 15 ° or more can be formed. Therefore, even when a fingerprint is attached, the contact angle is small, so the visibility is low and the fingerprint is inconspicuous.
- the surface treatment layer formed on the base material using the surface treatment agent containing the compound of the present invention has high surface slipperiness. That is, the surface treatment agent containing the compound of the present invention has a dynamic friction coefficient of preferably 0.30 or less, more preferably 0.25 or less, further preferably 0.20 or less, more preferably 0.15 or less, and further preferably. Can form a surface treatment layer of 0.10 or less.
- the surface treating agent of the present invention contains at least one (poly) ether group-containing silane compound represented by the formula (A1).
- the surface treatment agent of the present invention may be diluted with a solvent.
- a solvent is not particularly limited, and various general-purpose solvents can be used.
- the solvent contained in the surface treatment agent of the present invention includes acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, propylene glycol mono Ethyl ether acetate, propylene glycol monobutyl ether acetate, dipropylene glycol dimethyl ether pentane, hexane, heptane, octane, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, carbon disulfide, benzene, toluene, xylene, nitrobenzene,
- the surface treatment agent of the present invention may contain other components in addition to the (poly) ether group-containing silane compound of the present invention.
- Such other components include, but are not limited to, polyols and catalysts.
- the polyol As the polyol, the following formula: HO— (C a ′ H 2a ′ O) b ′ —OH [Where: a ′ is an integer from 1 to 6 independently for each unit enclosed in parentheses with b ′; b ′ is an integer of 1 to 300 independently at each occurrence. ]
- the compound represented by these may be sufficient.
- the polyol may be a block polymer or a random polymer. By adding a polyol, it is possible to obtain more excellent surface slipperiness, friction durability, and performance for reducing fingerprint visibility after wiping.
- — (C a ′ H 2a ′ O) b ′ — has the following formula: - (C 4 H 8 O) c '- (C 3 H 6 O) d' - (C 2 H 4 O) e '- (Where: c ′, d ′ and e ′ are each independently an integer of 0 to 300, such as an integer of 1 to 300, preferably an integer of 5 to 200, more preferably an integer of 10 to 100 in each occurrence; the sum of c ′, d ′ and e ′ is 1 to 200, preferably 5 to 200, more preferably 10 to 100; The order of presence of each repeating unit with parentheses c ′, d ′ or e ′ and enclosed in parentheses is arbitrary in the formula. ) It is group represented by these.
- -(C a ' H 2a' O) b ' - has the formula: -(C 4 H 8 O) c ' - -(C 3 H 6 O) d ' -, and-(C 2 H 4 O) e'- (Wherein c ′, d ′ and e ′ are each independently an integer of 1 to 300, preferably an integer of 5 to 200, more preferably an integer of 10 to 100). Is a group selected from
- the number average molecular weight of the polyol is preferably 1,000 to 30,000, more preferably 5,000 to 20,000, such as 8,000 to 20,000 or 10,000 to 20,000. possible.
- the polyol is, for example, from 0 to 500 with respect to a total of 100 parts by mass of the polyether group-containing silane compound of the present invention (in the case of 2 or more types, the total is the same). It may be contained in an amount of, preferably 0 to 400 parts by weight, more preferably 25 to 400 parts by weight.
- the average molecular weight of the polyol may be larger than the average molecular weight of the compound represented by the formula (A1) or the formula (A2).
- the catalyst examples include acids (eg, acetic acid, trifluoroacetic acid, etc.), bases (eg, ammonia, triethylamine, diethylamine, etc.), transition metals (eg, Ti, Ni, Sn, etc.), and the like.
- acids eg, acetic acid, trifluoroacetic acid, etc.
- bases eg, ammonia, triethylamine, diethylamine, etc.
- transition metals eg, Ti, Ni, Sn, etc.
- the catalyst promotes the hydrolysis and dehydration condensation of the (poly) ether group-containing silane compound of the present invention, and promotes the formation of the surface treatment layer.
- the surface treatment agent of the present invention can be made into a pellet by impregnating a porous material such as a porous ceramic material or metal fiber such as steel wool hardened in a cotton form.
- the pellet can be used for, for example, vacuum deposition.
- the article of the present invention includes a base material and a layer (surface treatment layer) formed on the surface of the base material from the surface treatment agent of the present invention.
- This article can be manufactured, for example, as follows.
- Substrates that can be used in the present invention include, for example, glass, sapphire glass, resin (natural or synthetic resin, such as a general plastic material, and may be a plate, film, or other form), metal ( It may be a single metal such as aluminum, copper, iron or a composite of an alloy, etc.), ceramics, semiconductor (silicon, germanium, etc.), fiber (woven fabric, non-woven fabric, etc.), fur, leather, wood, ceramics, stone, etc. It can be composed of any suitable material, such as a building member.
- the substrate is glass or sapphire glass.
- soda lime glass alkali aluminosilicate glass, borosilicate glass, alkali-free glass, crystal glass, and quartz glass are preferable, chemically strengthened soda lime glass, chemically strengthened alkali aluminosilicate glass, and chemical bond Particularly preferred is borosilicate glass.
- acrylic resin and polycarbonate are preferable.
- the material constituting the surface of the substrate may be an optical member material such as glass or transparent plastic.
- some layer (or film) such as a hard coat layer or an antireflection layer may be formed on the surface (outermost layer) of the substrate.
- the antireflection layer either a single-layer antireflection layer or a multilayer antireflection layer may be used.
- inorganic materials that can be used for the antireflection layer include SiO 2 , SiO, ZrO 2 , TiO 2 , TiO, Ti 2 O 3 , Ti 2 O 5 , Al 2 O 3 , Ta 2 O 5 , CeO 2 , MgO.
- the article to be manufactured is an optical glass component for a touch panel, a thin film using a transparent electrode such as indium tin oxide (ITO) or indium zinc oxide is provided on a part of the surface of the substrate (glass). It may be.
- ITO indium tin oxide
- the base material is an insulating layer, an adhesive layer, a protective layer, a decorative frame layer (I-CON), an atomized film layer, a hard coating film layer, a polarizing film, a phase difference film, And a liquid crystal display module or the like.
- the shape of the substrate is not particularly limited.
- the surface region of the base material on which the surface treatment layer is to be formed may be at least part of the surface of the base material, and can be appropriately determined according to the use and specific specifications of the article to be manufactured.
- a base material at least a surface portion thereof may be made of a material originally having a hydroxyl group.
- materials include glass, and metals (particularly base metals) on which a natural oxide film or a thermal oxide film is formed on the surface, ceramics, and semiconductors.
- it can be introduced to the surface of the substrate by applying some pretreatment to the substrate. Or increase it. Examples of such pretreatment include plasma treatment (for example, corona discharge) and ion beam irradiation.
- the plasma treatment can be preferably used for introducing or increasing hydroxyl groups on the surface of the base material and for cleaning the base material surface (removing foreign matter or the like).
- an interfacial adsorbent having a carbon-carbon unsaturated bond group is previously formed on the substrate surface by a monomolecular film by the LB method (Langmuir-Blodgett method) or chemical adsorption method. There is a method of forming in a form and then cleaving the unsaturated bond in an atmosphere containing oxygen, nitrogen or the like.
- the substrate may be made of a material containing at least a surface portion of a silicone compound having one or more other reactive groups, for example, Si—H groups, or an alkoxysilane.
- a film of the above-described surface treatment agent of the present invention is formed on the surface of the substrate, and this film is post-treated as necessary, thereby forming a surface treatment layer from the surface treatment agent of the present invention. To do.
- the film formation of the surface treatment agent of the present invention can be carried out by applying the surface treatment agent to the surface of the substrate so as to cover the surface.
- the coating method is not particularly limited. For example, wet coating methods and dry coating methods can be used.
- wet coating methods include dip coating, spin coating, flow coating, spray coating, roll coating, gravure coating and similar methods.
- Examples of dry coating methods include vapor deposition (usually vacuum vapor deposition), sputtering, CVD, and similar methods.
- Specific examples of the vapor deposition method include resistance heating, high-frequency heating using an electron beam, microwave, and the like, an ion beam, and similar methods.
- Specific examples of the CVD method include plasma-CVD, optical CVD, thermal CVD, and similar methods.
- the surface treatment agent of the present invention can be applied to the substrate surface after being diluted with a solvent.
- the following solvents are preferably used: acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol.
- the surface treatment agent of the present invention may be directly subjected to the dry coating method, or may be diluted with the above-described solvent and then subjected to the dry coating method.
- the film formation is preferably carried out so that the surface treatment agent of the present invention is present together with a catalyst for hydrolysis and dehydration condensation in the film.
- the catalyst may be added to the diluted solution of the surface treatment agent of the present invention immediately after the surface treatment agent of the present invention is diluted with a solvent and applied to the substrate surface.
- the surface treatment agent of the present invention added with a catalyst is subjected to vapor deposition (usually vacuum vapor deposition) as it is, or the surface treatment agent of the present invention added with a catalyst to a metal porous body such as iron or copper Vapor deposition (usually vacuum deposition) may be performed using a pellet-like material impregnated with.
- any suitable acid or base can be used for the catalyst.
- the acid catalyst for example, acetic acid, formic acid, trifluoroacetic acid and the like can be used.
- a base catalyst ammonia, organic amines, etc. can be used, for example.
- the membrane is post-treated as necessary.
- this post-processing is not specifically limited, For example, a water supply and drying heating may be implemented sequentially, and it may be implemented as follows in detail.
- the surface treatment agent of the present invention is formed on the substrate surface as described above, moisture is supplied to this film (hereinafter also referred to as “precursor film”).
- the method for supplying moisture is not particularly limited, and for example, methods such as dew condensation due to a temperature difference between the precursor film (and the substrate) and the surrounding atmosphere, or spraying of steam (steam) may be used.
- the supply of moisture is, for example, 0 to 250 ° C., preferably 60 ° C. or higher, more preferably 100 ° C. or higher, preferably 180 ° C. or lower, more preferably 150 ° C. or lower.
- the pressure at this time is not specifically limited, it can be simply a normal pressure.
- the precursor film is heated on the surface of the substrate in a dry atmosphere exceeding 60 ° C.
- the drying heating method is not particularly limited, and the temperature of the precursor film together with the base material is higher than 60 ° C., preferably higher than 100 ° C., for example, 250 ° C. or lower, preferably 180 ° C. or lower. What is necessary is just to arrange
- the above water supply and drying heating may be continuously performed by using superheated steam.
- Superheated steam is a gas obtained by heating saturated steam to a temperature higher than the boiling point, and exceeds 100 ° C. under normal pressure, generally 500 ° C. or lower, for example, 300 ° C. or lower, and has a boiling point. It is a gas that has become an unsaturated water vapor pressure by heating to a temperature exceeding.
- superheated steam at 250 ° C. or lower, preferably 180 ° C. or lower is preferably used for water supply and drying heating.
- the precursor film on the surface of the substrate comes into contact with the superheated steam, thereby the temperature of the superheated steam ( It will be heated to a temperature exceeding 100 ° C. under normal pressure. Therefore, if superheated steam is used, moisture supply and drying heating can be carried out continuously only by exposing the substrate on which the precursor film is formed to superheated steam.
- Post-processing can be performed as described above. It should be noted that such post-treatment can be performed to further improve friction durability, but is not essential for producing the articles of the present invention. For example, after applying the surface treating agent of the present invention to the surface of the substrate, it may be left still as it is.
- the surface treatment layer derived from the film of the surface treatment agent of the present invention is formed on the surface of the substrate, and the article of the present invention is manufactured.
- the surface treatment layer obtained by this has high friction durability.
- this surface treatment layer can easily make the attached fingerprints invisible, and further, depending on the composition of the surface treatment agent used, the water repellency, oil repellency, Dirty (for example, preventing adhesion of dirt such as fingerprints), waterproof (for preventing water from entering electronic parts), surface slipperiness (or lubricity, for example, wiping of dirt such as fingerprints, finger Etc.) and can be suitably used as a functional thin film.
- the article having the surface treatment layer obtained by the present invention is not particularly limited, but may be an optical member.
- the optical member include the following optical members: For example, a cathode ray tube (CRT: eg, TV, personal computer monitor), liquid crystal display, plasma display, organic EL display, inorganic thin film EL dot matrix display, rear projection type Display such as display, fluorescent display tube (VFD), field emission display (FED), front protective plate, antireflection plate, polarizing plate, antiglare plate, or antireflection film treatment on the surface of these displays Lenses such as eyeglasses; Touch panel sheets for devices such as mobile phones and personal digital assistants; Disc surfaces of optical discs such as Blu-ray (registered trademark) discs, DVD discs, CD-Rs, and MOs; Optical fa Eber: Clock display surface.
- Other articles having a surface treatment layer obtained by the present invention can include ceramic products, coated surfaces, fabric products, leather products, medical products, plasters, etc.
- the other article having the surface treatment layer obtained by the present invention may be a medical device or a medical material.
- the thickness of the surface treatment layer is not particularly limited. In the case of an optical member, the thickness of the surface treatment layer is in the range of 1 to 50 nm, preferably 1 to 30 nm, more preferably 1 to 15 nm. Optical performance, surface slipperiness, friction durability, and antifouling properties From the point of view, it is preferable.
- the articles obtained using the surface treating agent of the present invention have been described in detail.
- the use of the surface treating agent of the present invention, the usage method, the manufacturing method of the article, and the like are not limited to those exemplified above.
- Example 1 6.5 g of polytetramethylene glycol (molecular weight 650) was dissolved in 10 g of tetrahydrofuran, and 0.96 g of sodium hydride was added. Allyl bromide 7.3g was dripped and it stirred at 50 degree
- Completion of the reaction was confirmed by the disappearance of the isocyanate peak at 2260 cm ⁇ 1 by FT-IR.
- Comparative Example 1 Into a four-necked flask equipped with a dropping funnel, a stirrer, and a thermometer, 10.0 g of polytetramethylene glycol (molecular weight: 650) and 10.0 g of ethyl acetate were added and mixed by stirring to make the system uniform. Subsequently, a mixture of 3.80 g of 3- (triethoxysilyl) propyl isocyanate and 0.05 g of di-n-butyltin dilaurate as a catalyst was dropped from a dropping funnel, stirred and reacted at room temperature for 12 hours to obtain a compound 4 Got. Completion of the reaction was confirmed by the disappearance of the isocyanate peak at 2260 cm ⁇ 1 by FT-IR.
- Example 4 Compound 1 obtained in Example 1 was prepared so as to be an ethyl acetate solution having a concentration of 20 wt%, and a surface treatment agent was prepared.
- the surface treatment agent was vacuum-deposited (pressure 3.0 ⁇ 10 ⁇ 3 Pa) on chemically strengthened glass (Corning, “Gorilla” glass, thickness 0.7 mm).
- 2 mg of surface treating agent (that is, containing 0.4 mg of compound 1 of Example 1) was vapor deposited per chemically strengthened glass (55 mm ⁇ 100 mm). Thereafter, the chemically strengthened glass with a deposited film was allowed to stand for 24 hours in an atmosphere of a temperature of 20 ° C. and a humidity of 65%. Thereby, a vapor deposition film hardened and a surface treatment layer was formed.
- Example 5 A surface treatment agent was prepared and a surface treatment layer was formed in the same manner as in Example 4 except that the compound 2 of Example 2 was used instead of the compound of Example 1.
- Example 6 A surface treatment agent was prepared and a surface treatment layer was formed in the same manner as in Example 4 except that the compound 3 of Example 3 was used instead of the compound of Example 1.
- Comparative Example 2 A surface treatment agent was prepared and a surface treatment layer was formed in the same manner as in Example 4 except that the compound 4 of Comparative Example 1 was used instead of the compound of Example 1.
- Test example / Surface slipperiness evaluation (dynamic friction coefficient (COF) measurement)
- ⁇ surface property measuring machine
- ASTM surface property measuring machine
- the dynamic friction coefficient ( ⁇ ) was measured according to D4917. Specifically, the equipment on which the surface treatment layer is formed is horizontally arranged, the friction element (2 cm ⁇ 2 cm) is brought into contact with the exposed upper surface of the surface treatment layer, a load of 200 gf is applied thereon, and then the load is applied.
- the dynamic friction coefficient was measured by moving the friction piece in an equilibrium state at a speed of 500 mm / sec. The results are shown in Table 1.
- the substrate after the fingerprint adhesion test was visually wiped with a wipe of 100 gf, and the degree of wiping off the fingerprint was visually evaluated, and evaluated in three stages. 1: The fingerprint disappeared after wiping within 2 round trips. 2: The fingerprint disappeared after 3-5 reciprocations. Even after 3: 5 reciprocation, there was a fingerprint mark.
- the surface treatment layer formed by the surface treatment agent containing the compound of the present invention has low fingerprint visibility and high friction durability even when fingerprints are attached. It was done.
- the present invention can be suitably used for forming a surface treatment layer on the surface of a variety of substrates, particularly optical members that require transparency.
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Abstract
Description
R1は、OR4を表し;
R4は、水素原子または炭素数1~20のアルキル基を表し;
PE1は、各出現においてそれぞれ独立して、式:
-(CaH2aO)b-
(式中:
aは、bを付して括弧でくくられた単位毎にそれぞれ独立して、1~6の整数であり;
bは、各出現においてそれぞれ独立して、1~200の整数である。)
で表される基であり;
Yは、各出現においてそれぞれ独立して、単結合または-CONH-R5-NHCOO-を表し;
R5は、各出現においてそれぞれ独立して、二価の有機基を表し;
nは、1~50の整数であり;
PE2は、単結合または上記-(CaH2aO)b-基を表し;
Xは、それぞれ独立して、単結合または2~10価の有機基を表し;
Raは、各出現においてそれぞれ独立して、-Z-SiR71 pR72 qR73 rを表し;
Zは、各出現においてそれぞれ独立して、酸素原子または2価の有機基を表し;
R71は、各出現においてそれぞれ独立して、Ra’を表し;
Ra’は、Raと同意義であり;
Ra中、Z基を介して直鎖状に連結されるSiは最大で5個であり;
R72は、各出現においてそれぞれ独立して、水酸基または加水分解可能な基を表し;
R73は、各出現においてそれぞれ独立して、水素原子または低級アルキル基を表し;
pは、各出現においてそれぞれ独立して、0~3の整数であり;
qは、各出現においてそれぞれ独立して、0~3の整数であり;
rは、各出現においてそれぞれ独立して、0~3の整数であり;
1つのRaにおいて、p、qおよびrの和は3であり;
Rbは、各出現においてそれぞれ独立して、水酸基または加水分解可能な基を表し;
Rcは、各出現においてそれぞれ独立して、水素原子または低級アルキル基を表し;
kは、各出現においてそれぞれ独立して、0~3の整数であり;
lは、各出現においてそれぞれ独立して、0~3の整数であり;
mは、各出現においてそれぞれ独立して、0~3の整数であり;
αを付して括弧でくくられた単位において、k、lおよびmの和は3であり;
αは、それぞれ独立して、1~9の整数であり;
ただし、1つのXに結合する(SiRa kRb lRc m)α中には、RbまたはR72を有するSi原子が、合計で2つ以上存在する。]
で表される化合物が提供される。
-(CaH2aO)b-
(式中:
aは、bを付して括弧でくくられた単位毎にそれぞれ独立して、1~6の整数であり、好ましくは2~4の整数であり;
bは、各出現においてそれぞれ独立して、1~200の整数であり、好ましくは5~200の整数、より好ましくは5~100の整数、さらに好ましくは5~50の整数である。)
で表される基である。
-(CaH2aO)b-
(式中、aおよびbは、上記と同意義である。)
で表される基である。
-(C4H8O)c-(C3H6O)d-(C2H4O)e-
(式中:
c、dおよびeは、各出現においてそれぞれ独立して、0~200の整数、例えば1~200の整数、好ましくは5~200の整数、より好ましくは5~100の整数、さらに好ましくは5~50の整数であり;
c、dおよびeの和は1~200であり、好ましくは5~200、より好ましくは5~100、さらに好ましくは5~50であり;
添字c、dまたはe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。)
で表される基である。
-(C4H8O)c-(C3H6O)d-
(式中:
cおよびdは、各出現においてそれぞれ独立して、0~200の整数、例えば1~200の整数、好ましくは5~200の整数、より好ましくは5~100の整数、さらに好ましくは5~50の整数であり;
cおよびdの和は1~200であり、好ましくは5~200、より好ましくは5~100、さらに好ましくは5~50であり;
添字cまたはd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。)
で表される基である。
-(C4H8O)c-
-(C3H6O)d-、および
-(C2H4O)e-
(式中、c、dおよびeは、それぞれ独立して、1~200の整数、好ましくは5~200の整数、より好ましくは5~100の整数、さらに好ましくは5~50の整数である。)
から選択される基である。即ち、この態様において、PE1およびPE2は、それぞれ独立して、-(C4H8O)c-、-(C3H6O)d-、または-(C2H4O)e-で表されるホモポリマー単位である。好ましい態様において、式(A1)または(A2)中、少なくとも1つの-(C4H8O)c-ホモポリマー単位が存在する。また、式(A1)または(A2)中、-(C4H8O)c-ホモポリマー単位に加え、他の2種が存在してもよく、他の1種のみが存在してもよい。
-(C4H8O)c-、および
-(C3H6O)d-
(式中、cおよびdは、それぞれ独立して、1~200の整数、好ましくは5~200の整数、より好ましくは5~100の整数、さらに好ましくは5~50の整数である。)
から選択される基である。好ましい態様において、式(A1)または(A2)中、少なくとも1つの-(C4H8O)c-ホモポリマー単位を含む。
-(C4H8O)c-
(式中、cは、1~200の整数、好ましくは5~200の整数、より好ましくは5~100の整数、さらに好ましくは5~50の整数である。)
で表される基である。即ち、この態様において、PE1およびPE2は、-C4H8O-単位のみから成る。
-(CH2)x’- (式中、x’は、1~6の整数、例えば1~4の整数である。);
zは、0~10の整数、例えば0~4または1~4の整数である。)
zは、0~4の整数、例えば0~3または1~3の整数である。)
尚、xまたはyが0である場合、-(CH2)x-または-(CH2)y-は、それぞれ単結合(結合手)を意味する。
-(R30)r’-[(R31)p’-(Xa)q’]-
[式中:
R30は、-CONH-または-CO-、好ましくは-CONH-であり;
r’は、0または1であり、
R31は、単結合、-(CH2)s’-またはo-、m-もしくはp-フェニレン基を表し、好ましくは-(CH2)s’-であり、
s’は、1~20の整数、好ましくは1~6の整数、より好ましくは1~3の整数、さらにより好ましくは1または2であり、
Xaは、-(Xb)l’-を表し、
Xbは、各出現においてそれぞれ独立して、-O-、-S-、o-、m-もしくはp-フェニレン基、-C(O)O-、-Si(R33)2-、-(Si(R33)2O)m’-Si(R33)2-、-CONR34-、-O-CONR34-、-NR34-および-(CH2)n’-からなる群から選択される基を表し、
R33は、各出現においてそれぞれ独立して、フェニル基、C1-6アルキル基またはC1-6アルコキシ基を表し、好ましくはフェニル基またはC1-6アルキル基であり、より好ましくはメチル基であり、
R34は、各出現においてそれぞれ独立して、水素原子、フェニル基またはC1-6アルキル基(好ましくはメチル基)を表し、
m’は、各出現において、それぞれ独立して、1~100の整数、好ましくは1~20の整数であり、
n’は、各出現において、それぞれ独立して、1~20の整数、好ましくは1~6の整数、より好ましくは1~3の整数であり、
l’は、1~10の整数、好ましくは1~5の整数、より好ましくは1~3の整数であり、
p’は、0または1であり、
q’は、0または1であり、
ここに、p’およびq’の少なくとも一方は1であり、[(R31)p’-(Xa)q’]において、p’またはq’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任意である]
で表される2価の基が挙げられる。ここに、R31およびXa(典型的にはR31およびXaの水素原子)は、C1-3アルキル基から選択される1個またはそれ以上の置換基により置換されていてもよい。
-R30-C1-20アルキレン基、
-R30-R31-Xc-R32-、
-R30-Xd-R32-、
C1-20アルキレン基、
-R31-Xc-R32-、または
-Xd-R32-
[式中、R30、R31およびR32は、上記と同意義である。]
であり得る。
-R30-C1-20アルキレン基、
-R30-(CH2)s’-Xc-、
-R30-(CH2)s’-Xc-(CH2)t’-
-R30-Xd-、
-R30-Xd-(CH2)t’-、
C1-20アルキレン基、
-(CH2)s’-Xc-、
-(CH2)s’-Xc-(CH2)t’-
-Xd-、または
-Xd-(CH2)t’-
[式中、R30、s’およびt’は、上記と同意義である。]
である。
-O-、
-S-、
-C(O)O-、
-CONR34-、
-O-CONR34-、
-Si(R33)2-、
-(Si(R33)2O)m’-Si(R33)2-、
-O-(CH2)u’-(Si(R33)2O)m’-Si(R33)2-、
-O-(CH2)u’-Si(R33)2-O-Si(R33)2-CH2CH2-Si(R33)2-O-Si(R33)2-、
-O-(CH2)u’-Si(OCH3)2OSi(OCH3)2-、
-CONR34-(CH2)u’-(Si(R33)2O)m’-Si(R33)2-、
-CONR34-(CH2)u’-N(R34)-、または
-CONR34-(o-、m-またはp-フェニレン)-Si(R33)2-
[式中、R33、R34およびm’は、上記と同意義であり、
u’は1~20の整数、好ましくは2~6の整数、より好ましくは2~3の整数である。]を表す。Xcは、好ましくは-O-である。
-S-、
-C(O)O-、
-CONR34-、
-CONR34-(CH2)u’-(Si(R33)2O)m’-Si(R33)2-、
-CONR34-(CH2)u’-N(R34)-、または
-CONR34-(o-、m-またはp-フェニレン)-Si(R33)2-
[式中、各記号は、上記と同意義である。]
を表す。
-R30-C1-20アルキレン基、
-R30-(CH2)s’-Xc-(CH2)t’-、
-R30-Xd-(CH2)t’-、
C1-20アルキレン基、
-(CH2)s’-Xc-(CH2)t’-、または
-Xd-(CH2)t’-
[式中、各記号は、上記と同意義である。]
であり得る。
-R30-C1-20アルキレン基、
-R30-(CH2)s’-O-(CH2)t’-、
-R30-(CH2)s’-(Si(R33)2O)m’-Si(R33)2-(CH2)t’-、
-R30-(CH2)s’-O-(CH2)u’-(Si(R33)2O)m’-Si(R33)2-(CH2)t’-、
-R30-(CH2)s’-O-(CH2)t’-Si(R33)2 -(CH2)u’-Si(R33)2-(CvH2v)-、
C1-20アルキレン基、
-(CH2)s’-O-(CH2)t’-、
-(CH2)s’-(Si(R33)2O)m’-Si(R33)2-(CH2)t’-、
-(CH2)s’-O-(CH2)u’-(Si(R33)2O)m’-Si(R33)2-(CH2)t’-、または
-(CH2)s’-O-(CH2)t’-Si(R33)2 -(CH2)u’-Si(R33)2-(CvH2v)-
[式中、-R30、R33、m’、s’、t’およびu’は、上記と同意義であり、vは1~20の整数、好ましくは2~6の整数、より好ましくは2~3の整数である。]
である。
Dは、
-CH2O(CH2)2-、
-CH2O(CH2)3-、
-CF2O(CH2)3-、
-(CH2)2-、
-(CH2)3-、
-(CH2)4-、
-CONH-(CH2)2-、
-CONH-(CH2)3-、
-CONH-(CH2)4-、
-CO-(CH2)2-、
-CO-(CH2)3-、
-CO-(CH2)4-、
-CON(CH3)-(CH2)3-、
-CON(Ph)-(CH2)3-(式中、Phはフェニルを意味する)、および
から選択される基であり、
Eは、-(CH2)n-(nは2~6の整数)であり、
Dは、分子主鎖のPE2に結合し、Eは、Si原子に結合する。]
-CONH-(CH2)2-、
-CONH-(CH2)3-、
-CONH-(CH2)4-、
-CO-(CH2)2-、
-CO-(CH2)3-、
-CO-(CH2)4-、
-CH2O(CH2)2-、
-CH2O(CH2)3-、
-CH2O(CH2)6-、
-CH2O(CH2)3Si(CH3)2OSi(CH3)2(CH2)2-、
-CH2O(CH2)3Si(CH3)2OSi(CH3)2OSi(CH3)2(CH2)2-、
-CH2O(CH2)3Si(CH3)2O(Si(CH3)2O)2Si(CH3)2(CH2)2-、
-CH2O(CH2)3Si(CH3)2O(Si(CH3)2O)3Si(CH3)2(CH2)2-、
-CH2O(CH2)3Si(CH3)2O(Si(CH3)2O)10Si(CH3)2(CH2)2-、
-CH2O(CH2)3Si(CH3)2O(Si(CH3)2O)20Si(CH3)2(CH2)2-、
-CH2OCF2CHFOCF2-、
-CH2OCF2CHFOCF2CF2-、
-CH2OCF2CHFOCF2CF2CF2-、
-CH2OCH2CF2CF2OCF2-、
-CH2OCH2CF2CF2OCF2CF2-、
-CH2OCH2CF2CF2OCF2CF2CF2-、
-CH2OCH2CF2CF2OCF(CF3)CF2OCF2-、
-CH2OCH2CF2CF2OCF(CF3)CF2OCF2CF2-、
-CH2OCH2CF2CF2OCF(CF3)CF2OCF2CF2CF2-、
-CH2OCH2CHFCF2OCF2-、
-CH2OCH2CHFCF2OCF2CF2-、
-CH2OCH2CHFCF2OCF2CF2CF2-、
-CH2OCH2CHFCF2OCF(CF3)CF2OCF2-、
-CH2OCH2CHFCF2OCF(CF3)CF2OCF2CF2-、
-CH2OCH2CHFCF2OCF(CF3)CF2OCF2CF2CF2-
-CH2OCH2(CH2)7CH2Si(OCH3)2OSi(OCH3)2(CH2)2Si(OCH3)2OSi(OCH3)2(CH2)2-、
-CH2OCH2CH2CH2Si(OCH3)2OSi(OCH3)2(CH2)3-、
-(CH2)2-、
-(CH2)3-、
-(CH2)4-、
-(CH2)6-、
-CONH-(CH2)3-、
-CON(CH3)-(CH2)3-、
-CON(Ph)-(CH2)3-(式中、Phはフェニルを意味する)、
-CONH-(CH2)6-、
-CON(CH3)-(CH2)6-、
-CON(Ph)-(CH2)6-(式中、Phはフェニルを意味する)、
-CONH-(CH2)2NH(CH2)3-、
-CONH-(CH2)6NH(CH2)3-、
-CH2O-CONH-(CH2)3-、
-CH2O-CONH-(CH2)6-、
-S-(CH2)3-、
-(CH2)2S(CH2)3-、
-CONH-(CH2)3Si(CH3)2OSi(CH3)2(CH2)2-、
-CONH-(CH2)3Si(CH3)2OSi(CH3)2OSi(CH3)2(CH2)2-、
-CONH-(CH2)3Si(CH3)2O(Si(CH3)2O)2Si(CH3)2(CH2)2-、
-CONH-(CH2)3Si(CH3)2O(Si(CH3)2O)3Si(CH3)2(CH2)2-、
-CONH-(CH2)3Si(CH3)2O(Si(CH3)2O)10Si(CH3)2(CH2)2-、
-CONH-(CH2)3Si(CH3)2O(Si(CH3)2O)20Si(CH3)2(CH2)2-
-C(O)O-(CH2)3-、
-C(O)O-(CH2)6-、
-CH2-O-(CH2)3-Si(CH3)2-(CH2)2-Si(CH3)2-(CH2)2-、
-CH2-O-(CH2)3-Si(CH3)2-(CH2)2-Si(CH3)2-CH(CH3)-、
-CH2-O-(CH2)3-Si(CH3)2-(CH2)2-Si(CH3)2-(CH2)3-、
-CH2-O-(CH2)3-Si(CH3)2-(CH2)2-Si(CH3)2-CH(CH3)-CH2-、
R41は、それぞれ独立して、水素原子、フェニル基、炭素数1~6のアルキル基、またはC1-6アルコキシ基好ましくはメチル基であり;
各X1基において、Tのうち任意のいくつかは、分子主鎖のPE2に結合する以下の基:
-CH2O(CH2)2-、
-CH2O(CH2)3-、
-CF2O(CH2)3-、
-(CH2)2-、
-(CH2)3-、
-(CH2)4-、
-CONH-(CH2)2-、
-CONH-(CH2)3-、
-CONH-(CH2)4-、
-CO-(CH2)2-、
-CO-(CH2)3-、
-CO-(CH2)4-、
-CON(CH3)-(CH2)3-、
-CON(Ph)-(CH2)3-(式中、Phはフェニルを意味する)、または
であり、別のTのいくつかは、Si原子に結合する-(CH2)n”-(n”は2~6の整数)であり、存在する場合、残りは、それぞれ独立して、メチル基、フェニル基またはC1-6アルコキシ基である。
[式中:
R61は、それぞれ独立して、二価の炭化水素基を表し;
R62は、β価の有機基を表し;
βは、2~6の整数であり;
R63は、-O-R67(OR68)s(O-X1a-)tを表し;
R67は、γ価の有機基を表し;
γは、2~8の整数であり;
R68は、水素原子または炭素数1~6のアルキル基であり;
X1aは、二価の有機基であって、上記したX1aと同意義であり;
sは、0~6の整数であり;
tは、1~7の整数であり;
sとtの和は、γ-1である。]
で表される基である。
HO-(Ca’H2a’O)b’-OH
[式中:
a’は、b’を付して括弧でくくられた単位毎にそれぞれ独立して、1~6の整数であり;
b’は、各出現においてそれぞれ独立して、1~300の整数である。]
で表される化合物であり得る。当該ポリオールは、ブロックポリマーであっても、ランダムポリマーであってもよい。ポリオールを加えることにより、より優れた表面滑り性、摩擦耐久性、拭き取った後の指紋視認性を低下させる性能を得ることができる。
-(C4H8O)c’-(C3H6O)d’-(C2H4O)e’-
(式中:
c’、d’およびe’は、各出現においてそれぞれ独立して、0~300の整数、例えば1~300の整数、好ましくは5~200の整数、より好ましくは10~100の整数であり;
c’、d’およびe’の和は1~200であり、好ましくは5~200、より好ましくは10~100であり;
添字c’、d’またはe’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。)
で表される基である。
-(C4H8O)c’-
-(C3H6O)d’-、および
-(C2H4O)e’-
(式中、c’、d’およびe’は、それぞれ独立して、1~300の整数、好ましくは5~200の整数、より好ましくは10~100の整数である。)
から選択される基である。
樹脂としては、アクリル樹脂、ポリカーボネートが好ましい。
ポリテトラメチレングリコール(分子量650)6.5gをテトラヒドロフラン10gに溶解させ、水素化ナトリウム0.96gを加えた。アリルブロミド7.3gを滴下し、50度で3時間撹拌した。室温まで放冷した後、飽和塩化アンモニウム水溶液70mlをゆっくり加え、分液後上層を回収し、溶剤および未反応物を減圧留去した。得られたオイル状の生成物5gをトルエン10g、テトラメチルシクロテトラシロキサン3.6g、1,3-ジビニルー1,1,3,3-テトラメチルジシロキサン白金(0)錯体のキシレン溶液0.25g(Pt単体として5mgを含有)の混合溶液に滴下し、60度で3時間撹拌した。その後、溶剤および未反応物を減圧留去した。得られた化合物8.5g、トルエン10g、ビニルトリメトキシシラン8.3g、1,3-ジビニルー1,1,3,3-テトラメチルジシロキサン白金(0)錯体のキシレン溶液0.25g(Pt単体として5mgを含有)を混合し、60℃で5時間撹拌した。その後活性炭1gを加え室温で一晩撹拌した。活性炭を濾過した後、溶剤および未反応物を減圧留去したところオイル状の生成物13gを得た。1H-NMRより下記式に示される化合物であることを確認した。
滴下漏斗、撹拌機、温度計を備えた4ツ口フラスコにグリセリン2.0g、酢酸エチルを5g入れ撹拌し、撹拌混合し、系内を均一にした。次いで[OH]/[NCO]=3/2になるように3-(トリエトキシシリル)プロピルイソシアネート5.74g、および触媒としてのジ-n-ブチルスズジラウレート0.05gの混合物を滴下漏斗より滴下し、撹拌し室温にて12時間反応させた。FT-IRにて2260cm-1のイソシアネートのピーク消失を確認した後、3官能イソシアネートであるスミジュールN3300(住友化学社製)を[OH]/[NCO]=2/3の比率になるように3.56g秤量し、同重量の酢酸エチルに溶解させて滴下し、撹拌反応させ、イソシアネート基を有する4官能シラン化合物Aを得た。次いで得られたシラン化合物Aとポリテトラメチレングリコール(分子量650)を[OH]/[NCO]=2/1になるよう混合し、1分子当たり平均4個のシランを有する化合物2を得た。FT-IRにて2260cm-1のイソシアネートのピーク消失で反応の完了を確認した。
シラン化合物Aとポリテトラメチレングリコール(分子量650)を用い、[OH]/[NCO]=1/1の比率になるよう混合反応させ、1分子当たり平均8個のシラン分子を有する化合物3(代表的には、下記構造式を有する)を得た。FT-IRにて2260cm-1のイソシアネートのピーク消失で反応の完了を確認した。
滴下漏斗、撹拌機、温度計を備えた4ツ口フラスコにポリテトラメチレングリコール(分子量650)を10.0g、酢酸エチルを10.0g投入し、撹拌混合し、系内を均一にした。次いで、3-(トリエトキシシリル)プロピルイソシアネートを3.80g、および触媒としてのジ-n-ブチルスズジラウレート0.05gの混合物を滴下漏斗より滴下し、撹拌し室温にて12時間反応させ、化合物4を得た。FT-IRにて2260cm-1のイソシアネートのピーク消失で反応の完了を確認した。
実施例4
上記実施例1で得た化合物1を、濃度20wt%の酢酸エチル溶液になるよう調製し、表面処理剤を調製した。表面処理剤を化学強化ガラス(コーニング社製、「ゴリラ」ガラス、厚さ0.7mm)上に真空蒸着(圧力3.0×10-3Pa)した。化学強化ガラス1枚(55mm×100mm)あたり、表面処理剤2mg(即ち、実施例1の化合物1を0.4mg含有)を蒸着させた。その後、蒸着膜付き化学強化ガラスを、温度20℃および湿度65%の雰囲気下で24時間静置した。これにより、蒸着膜が硬化して、表面処理層が形成された。
実施例1の化合物に代えて、実施例2の化合物2を用いたこと以外は、実施例4と同様にして、表面処理剤を調製し、表面処理層を形成した。
実施例1の化合物に代えて、実施例3の化合物3を用いたこと以外は、実施例4と同様にして、表面処理剤を調製し、表面処理層を形成した。
実施例1の化合物に代えて、比較例1の化合物4を用いたこと以外は、実施例4と同様にして、表面処理剤を調製し、表面処理層を形成した。
・表面滑り性評価(動摩擦係数(COF)の測定)
上記の実施例4~6および比較例2にて基材表面に形成された表面処理層について、表面性測定機(Labthink社製 FPT-1)を用いて、摩擦子として紙を使用し、ASTM D4917に準拠し、動摩擦係数(-)を測定した。具体的には、表面処理層を形成した機材を水平配置し、摩擦子(2cm×2cm)を表面処理層の露出上面に接触させ、その上に200gfの荷重を付与し、その後、荷重を加えた状況で摩擦子を500mm/秒の速度で平衡移動させて動摩擦係数を測定した。結果を表1に示す。
上記の実施例4~6および比較例2にて基材表面に形成された表面処理層について、付着した指紋の視認性、拭取り性を評価した。具体的には、指紋を付着させた処理基材をアルミ金属板の上に載せ、暗室内で基材に対し60度の入射角で蛍光灯の光を当て、光源と逆側60度の角度から基材に付着した指紋の見え方を目視にて確認、以下3段階で評価した。
1:指紋付着部が全く見えない。
2:指紋付着部がわずかに見える。
3:指紋付着部が白くくっきり見える。
指紋付着試験後の基材をキムワイプにて、100gfの荷重で拭取り指紋の拭取れ具合を目視で確認、以下3段階で評価した。
1:2往復以内の拭取りで指紋が見えなくなった。
2:3~5往復の拭きとりで指紋が見えなくなった。
3:5往復でも指紋の跡が残った。
水およびn-ヘキサデカンの静的接触角を、接触角計(協和界面科学社製、「DropMaster」)を用いて、それぞれ1μLの液量で測定した。結果を表1に示す。
Claims (21)
- 下記一般式(A1)または(A2):
R1は、OR4を表し;
R4は、水素原子または炭素数1~20のアルキル基を表し;
PE1は、各出現においてそれぞれ独立して、式:
-(CaH2aO)b-
(式中:
aは、bを付して括弧でくくられた単位毎にそれぞれ独立して、1~6の整数であり;
bは、各出現においてそれぞれ独立して、1~200の整数である。)
で表される基であり;
Yは、各出現においてそれぞれ独立して、単結合または-CONH-R5-NHCOO-を表し;
R5は、各出現においてそれぞれ独立して、二価の有機基を表し;
nは、1~50の整数であり;
PE2は、単結合または上記-(CaH2aO)b-基を表し;
Xは、それぞれ独立して、単結合または2~10価の有機基を表し;
Raは、各出現においてそれぞれ独立して、-Z-SiR71 pR72 qR73 rを表し;
Zは、各出現においてそれぞれ独立して、酸素原子または2価の有機基を表し;
R71は、各出現においてそれぞれ独立して、Ra’を表し;
Ra’は、Raと同意義であり;
Ra中、Z基を介して直鎖状に連結されるSiは最大で5個であり;
R72は、各出現においてそれぞれ独立して、水酸基または加水分解可能な基を表し;
R73は、各出現においてそれぞれ独立して、水素原子または低級アルキル基を表し;
pは、各出現においてそれぞれ独立して、0~3の整数であり;
qは、各出現においてそれぞれ独立して、0~3の整数であり;
rは、各出現においてそれぞれ独立して、0~3の整数であり;
1つのRaにおいて、p、qおよびrの和は3であり;
Rbは、各出現においてそれぞれ独立して、水酸基または加水分解可能な基を表し;
Rcは、各出現においてそれぞれ独立して、水素原子または低級アルキル基を表し;
kは、各出現においてそれぞれ独立して、0~3の整数であり;
lは、各出現においてそれぞれ独立して、0~3の整数であり;
mは、各出現においてそれぞれ独立して、0~3の整数であり;
αを付して括弧でくくられた単位において、k、lおよびmの和は3であり;
αは、それぞれ独立して、1~9の整数であり;
ただし、1つのXに結合する(SiRa kRb lRc m)α中には、RbまたはR72を有するSi原子が、合計で2つ以上存在する。]
で表される化合物。 - Xが、それぞれ独立して、3~10価の有機基を表し、αが、それぞれ独立して、2~9の整数であることを特徴とする、請求項1に記載の化合物。
- kが1~3の整数であることを特徴とする、請求項1または2に記載の化合物。
- PE1およびPE2における-(CaH2aO)b-が、それぞれ独立して、式:
-(C4H8O)c-(C3H6O)d-(C2H4O)e-
(式中:
c、dおよびeは、それぞれ独立して、0~200の整数であり;
c、dおよびeの和は1~200であり;
添字c、dまたはe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。)
で表される基であることを特徴とする、請求項1~4のいずれか1項に記載の化合物。 - PE1およびPE2が、各出現においてそれぞれ独立して、
-(C4H8O)c-
-(C3H6O)d-、および
-(C2H4O)e-
(式中、c、dおよびeは、それぞれ独立して、1~200の整数である。)
から選択される基であることを特徴とする、請求項1~5のいずれか1項に記載の化合物。 - PE1およびPE2が、各出現においてそれぞれ独立して、式:
-(C4H8O)c-
(式中、cは、1~200の整数である。)
で表される基であることを特徴とする、請求項1~6のいずれか1項に記載の化合物。 - C4H8Oが、CH2CH2CH2CH2Oであり;
C3H6Oが、CH2CHCH3Oであり;
C2H4Oが、CH2CH2Oである
ことを特徴とする、請求項5~7のいずれか1項に記載の化合物。 - Xが、下記式:
-CONH-R61-R62(R61-NHCO-R63)β-1
[式中:
R61は、それぞれ独立して、二価の炭化水素基を表し;
R62は、β価の有機基を表し;
βは、2~6の整数であり;
R63は、-O-R67(OR68)s(O-X1-)tを表し;
R67は、γ価の有機基を表し;
γは、2~8の整数であり;
R68は、水素原子または炭素数1~6のアルキル基であり;
X1は、二価の有機基を表し;
sは、0~6の整数であり;
tは、1~7の整数であり;
sとtの和は、γ-1である。]
で表される基である、請求項1~9のいずれか1項に記載の化合物。 - PE1の数平均分子量が、500~10,000であることを特徴とする、請求項1~11のいずれか1項に記載の化合物。
- ガラス転移温度が、-70℃~40℃の範囲にあることを特徴とする、請求項1~12のいずれか1項に記載の化合物。
- 請求項1~13のいずれか1項に記載の式(A1)または式(A2)で表される少なくとも1種の化合物を含有する、表面処理剤。
- さらに溶媒を含む、請求項14に記載の表面処理剤。
- さらに下記式:
HO-(Ca’H2a’O)b’-OH
[式中:
a’は、b’を付して括弧でくくられた単位毎にそれぞれ独立して、1~6の整数であり;
b’は、各出現においてそれぞれ独立して、1~300の整数である。]
で表されるポリオールを含む、請求項14または15に記載の表面処理剤。 - n-ヘキサデカンに対する接触角が40°以下である表面処理層を形成することができる、請求項14~16のいずれか1項に記載の表面処理剤。
- 動摩擦係数が、0.30以下である表面処理層を形成することができる、請求項14~17のいずれか1項に記載の表面処理剤。
- 基材と、該基材の表面に、請求項14~18のいずれか1項に記載の表面処理剤より形成された層とを含む物品。
- 前記物品が光学部材である、請求項19に記載の物品。
- 前記物品がディスプレイまたはタッチパネルである、請求項19または20に記載の物品。
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TWI637977B (zh) * | 2015-06-12 | 2018-10-11 | 大金工業股份有限公司 | 表面處理劑 |
WO2022059961A1 (ko) * | 2020-09-21 | 2022-03-24 | 주식회사 쎄코 | 초박형 강도보강 코팅제용 화합물 이를 포함하는 강도보강 코팅제 |
Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01125390A (ja) * | 1987-11-10 | 1989-05-17 | Sagami Chem Res Center | 二官能性オリゴエチレンオキシド誘導体 |
JPH05255508A (ja) * | 1991-12-05 | 1993-10-05 | General Electric Co <Ge> | 紫外線硬化性エポキシシリコーン−ポリエーテルブロック共重合体 |
JPH0625262A (ja) * | 1992-04-23 | 1994-02-01 | Bayer Ag | 芳香族ポリカーボネートの熱安定化 |
JPH07179480A (ja) * | 1993-06-16 | 1995-07-18 | Osi Specialties Inc | 表面活性シロキサンコーテイング化合物およびコーテイング中でのそれらの使用 |
WO1997001565A1 (en) * | 1995-06-28 | 1997-01-16 | E.I. Du Pont De Nemours And Company | Molecular and oligomeric silane precursors to network materials |
JP2001131243A (ja) * | 1999-11-04 | 2001-05-15 | Shin Etsu Chem Co Ltd | 液状放射線硬化型樹脂組成物、光ファイバ用被覆材及び光ファイバ |
JP2005281143A (ja) * | 2004-03-26 | 2005-10-13 | Neos Co Ltd | アルコキシシラン化合物 |
JP2006274005A (ja) * | 2005-03-29 | 2006-10-12 | Dainippon Ink & Chem Inc | 光ファイバー被覆用樹脂組成物及びそれを用いた光ファイバー素線 |
JP2008044934A (ja) * | 2006-08-16 | 2008-02-28 | Samsung Sdi Co Ltd | シラン化合物、それを採用した有機電解液及びリチウム電池 |
JP2011068777A (ja) * | 2009-09-25 | 2011-04-07 | Shin-Etsu Chemical Co Ltd | ω末端にポリアルキレンオキシド基を有する片末端反応性オルガノポリシロキサン及びその製造方法。 |
JP2013076094A (ja) * | 2013-01-28 | 2013-04-25 | Asahi Glass Co Ltd | 硬化性組成物 |
JP2013124362A (ja) * | 2011-12-16 | 2013-06-24 | Dow Corning Toray Co Ltd | オルガノポリシロキサン−ポリオキシアルキレンブロック共重合体の製造方法 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1154853A (en) * | 1965-08-26 | 1969-06-11 | Gen Electric | Improvements in Curable Compositions |
WO1997007155A1 (fr) | 1995-08-11 | 1997-02-27 | Daikin Industries, Ltd. | Fluoropolymeres organiques au silicium et leur emploi |
CN103551076B (zh) | 2005-04-01 | 2016-07-06 | 大金工业株式会社 | 表面改性剂 |
WO2008121375A2 (en) * | 2007-03-29 | 2008-10-09 | Pacific Biosciences Of California, Inc. | Modified surfaces for immobilization of active molecules |
JP2013060354A (ja) | 2011-08-19 | 2013-04-04 | Central Glass Co Ltd | 耐指紋性被膜形成処理剤及び該被膜を有する耐指紋性ガラス |
WO2013180203A1 (ja) * | 2012-05-31 | 2013-12-05 | 株式会社カネカ | 複数の反応性ケイ素基を有する末端構造を有する重合体、およびその製造方法および利用 |
JP5936448B2 (ja) * | 2012-06-01 | 2016-06-22 | 関西ペイント株式会社 | 塗料組成物及び塗装物品 |
JP2014065827A (ja) | 2012-09-26 | 2014-04-17 | Dic Corp | トップコート剤ならびにそれを用いて得られたトップコート層を備えた表示装置及びタッチパネル |
FR3005052B1 (fr) | 2013-04-30 | 2015-04-17 | Oreal | Compose adapte au maquillage et/ou soin des ongles |
TWI637977B (zh) | 2015-06-12 | 2018-10-11 | 大金工業股份有限公司 | 表面處理劑 |
EP3348560A1 (en) * | 2017-01-16 | 2018-07-18 | Spago Nanomedical AB | Chemical compounds for coating of nanostructures |
-
2016
- 2016-06-08 TW TW105118323A patent/TWI644942B/zh active
- 2016-06-10 KR KR1020177035161A patent/KR102084634B1/ko active IP Right Grant
- 2016-06-10 CN CN201680033924.9A patent/CN107636001B/zh active Active
- 2016-06-10 WO PCT/JP2016/067418 patent/WO2016199908A1/ja active Application Filing
- 2016-06-10 JP JP2017523724A patent/JP6443547B2/ja active Active
- 2016-06-10 EP EP16807613.1A patent/EP3309165B1/en active Active
- 2016-06-10 US US15/735,268 patent/US10696788B2/en active Active
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01125390A (ja) * | 1987-11-10 | 1989-05-17 | Sagami Chem Res Center | 二官能性オリゴエチレンオキシド誘導体 |
JPH05255508A (ja) * | 1991-12-05 | 1993-10-05 | General Electric Co <Ge> | 紫外線硬化性エポキシシリコーン−ポリエーテルブロック共重合体 |
JPH0625262A (ja) * | 1992-04-23 | 1994-02-01 | Bayer Ag | 芳香族ポリカーボネートの熱安定化 |
JPH07179480A (ja) * | 1993-06-16 | 1995-07-18 | Osi Specialties Inc | 表面活性シロキサンコーテイング化合物およびコーテイング中でのそれらの使用 |
WO1997001565A1 (en) * | 1995-06-28 | 1997-01-16 | E.I. Du Pont De Nemours And Company | Molecular and oligomeric silane precursors to network materials |
JP2001131243A (ja) * | 1999-11-04 | 2001-05-15 | Shin Etsu Chem Co Ltd | 液状放射線硬化型樹脂組成物、光ファイバ用被覆材及び光ファイバ |
JP2005281143A (ja) * | 2004-03-26 | 2005-10-13 | Neos Co Ltd | アルコキシシラン化合物 |
JP2006274005A (ja) * | 2005-03-29 | 2006-10-12 | Dainippon Ink & Chem Inc | 光ファイバー被覆用樹脂組成物及びそれを用いた光ファイバー素線 |
JP2008044934A (ja) * | 2006-08-16 | 2008-02-28 | Samsung Sdi Co Ltd | シラン化合物、それを採用した有機電解液及びリチウム電池 |
JP2011068777A (ja) * | 2009-09-25 | 2011-04-07 | Shin-Etsu Chemical Co Ltd | ω末端にポリアルキレンオキシド基を有する片末端反応性オルガノポリシロキサン及びその製造方法。 |
JP2013124362A (ja) * | 2011-12-16 | 2013-06-24 | Dow Corning Toray Co Ltd | オルガノポリシロキサン−ポリオキシアルキレンブロック共重合体の製造方法 |
JP2013076094A (ja) * | 2013-01-28 | 2013-04-25 | Asahi Glass Co Ltd | 硬化性組成物 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2019044179A (ja) * | 2017-09-05 | 2019-03-22 | Agc株式会社 | 化合物、組成物、表面処理剤、物品および化合物の製造方法 |
WO2020066534A1 (ja) * | 2018-09-28 | 2020-04-02 | ダイキン工業株式会社 | 表面処理剤 |
JP2020090652A (ja) * | 2018-09-28 | 2020-06-11 | ダイキン工業株式会社 | 表面処理剤 |
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JPWO2016199908A1 (ja) | 2018-02-08 |
EP3309165A1 (en) | 2018-04-18 |
TWI644942B (zh) | 2018-12-21 |
KR102084634B1 (ko) | 2020-03-04 |
CN107636001B (zh) | 2020-11-03 |
EP3309165A4 (en) | 2019-03-06 |
JP6443547B2 (ja) | 2018-12-26 |
EP3309165B1 (en) | 2020-09-02 |
US20180171144A1 (en) | 2018-06-21 |
KR20180005681A (ko) | 2018-01-16 |
TW201708310A (zh) | 2017-03-01 |
US10696788B2 (en) | 2020-06-30 |
CN107636001A (zh) | 2018-01-26 |
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