WO2024018654A1 - 表面層、光学部材、眼鏡、及び表面層形成用材料 - Google Patents

表面層、光学部材、眼鏡、及び表面層形成用材料 Download PDF

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WO2024018654A1
WO2024018654A1 PCT/JP2023/002999 JP2023002999W WO2024018654A1 WO 2024018654 A1 WO2024018654 A1 WO 2024018654A1 JP 2023002999 W JP2023002999 W JP 2023002999W WO 2024018654 A1 WO2024018654 A1 WO 2024018654A1
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Prior art keywords
group
surface layer
component
bond
moiety
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PCT/JP2023/002999
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English (en)
French (fr)
Japanese (ja)
Inventor
廣斗 沼澤
直之 河目
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Canon Optron Inc
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Canon Optron Inc
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Priority to JP2023549930A priority Critical patent/JP7507983B2/ja
Priority to CN202380036931.4A priority patent/CN119096169A/zh
Priority to DE112023003193.2T priority patent/DE112023003193T5/de
Publication of WO2024018654A1 publication Critical patent/WO2024018654A1/ja
Priority to JP2024098225A priority patent/JP2024120006A/ja
Priority to US18/912,949 priority patent/US20250035822A1/en
Anticipated expiration legal-status Critical
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    • 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
    • C09D123/00—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers
    • C09D123/02—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
    • C09D123/025—Copolymer of an unspecified olefine with a monomer other than an olefine
    • 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
    • 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
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts
    • G02C7/02—Lenses; Lens systems ; Methods of designing lenses
    • 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 disclosure relates to a surface layer with excellent workability and stain resistance, an optical member having the surface layer, and eyeglasses having the optical member.
  • the present disclosure also provides a surface layer forming material that forms a surface layer with excellent workability and antifouling properties, a surface layer formed using the surface layer forming material, an optical member having the surface layer, and
  • the present invention relates to eyeglasses having optical members.
  • Optical members such as anti-reflection films, optical filters, optical lenses, and eyeglass lenses generally have anti-reflection films formed of inorganic materials in order to suppress reflection of light.
  • Antireflection films made of inorganic materials have high surface free energy. Due to its high surface free energy, dirt such as fingerprints, sebum, sweat, and cosmetics often adhere to it when used by people. Further, there is a problem in that attached dirt is difficult to remove.
  • Patent Documents 1 and 2 propose techniques for imparting properties to the surface of an optical member that make it difficult for dirt to adhere to it and to easily remove it even if it does adhere.
  • optical members that have surfaces that have properties that prevent dirt from adhering to them and that are easy to remove even if they do (hereinafter, such performance is also referred to as "antifouling properties” or “antifouling properties”) Since the force is small and the surface is slippery, it is difficult to stably fix the optical member when processing the shape, making it difficult to process.
  • Patent Document 3 discloses that a resin made of an organic compound, inorganic oxide fine particles, and an organosilicon compound represented by a predetermined general formula or a hydrolyzate thereof are coated on an oil-repellent coat film.
  • a protective film is formed by the coating liquid contained as an active ingredient, and the composition ratio of resin made of an organic compound and inorganic oxide fine particles and the content of an organosilicon compound or its hydrolyzate expressed by a predetermined general formula.
  • a spectacle lens is disclosed in which by setting the amount within a predetermined range, even if an oil-repellent coating film is provided, it is possible to perform beading processing using the same holding method as conventional spectacle lenses.
  • each of the two or more types of silane compounds is used as a single component.
  • the highest dynamic friction coefficient value is set to 1.4 times or more of the lowest dynamic friction coefficient value of the lens surface formed as A spectacle lens is disclosed in which the lubricity of the lens surface can be reduced to the extent that it can be molded.
  • Patent Documents 3 and 4 are still not sufficient in terms of fixation during processing, and there is a desire for an antifouling surface that has both processing stability and antifouling properties. There is.
  • the present disclosure provides a surface layer that has both stability of fixation during processing and antifouling properties, an optical member having the surface layer, and eyeglasses. Further, the present disclosure provides a surface layer forming material that forms a surface layer that has both stability of fixation during processing and antifouling properties.
  • the surface layer of the present disclosure is a surface layer containing at least component A and component B,
  • the component A has a siloxane moiety containing a siloxane bond
  • Component B has an organic moiety having at least one bond selected from the group consisting of a saturated hydrocarbon bond, an unsaturated hydrocarbon bond, a carbon-oxygen double bond, and a carbon-nitrogen double bond, and the following general formula (3) R 3 -Y-R 4 (3)
  • An alkyl compound having the structure shown in The sites represented by Y are [C i H 2i-2 ] j1 , [C i H 2i ] j2 , [C 6 H 4 ] j3, [C i+1 H 2i-1 Cl] j4 , [C i H i Cl] j5 , [C 5 H 4 O 3 ] j 6 , [C 3 H 6 N] j 7 and [C 4 H 6 O 2 N] j 8 including, The i, j 1 , j
  • the surface layer forming material of the present disclosure is a surface layer forming material containing at least component A and component B
  • the component A has a siloxane moiety containing at least a siloxane bond
  • Component B has an organic moiety having at least one bond selected from the group consisting of a saturated hydrocarbon bond, an unsaturated hydrocarbon bond, a carbon-oxygen double bond, and a carbon-nitrogen double bond, and the following general formula (3) R 3 -Y-R 4 (3)
  • An alkyl compound having the structure shown in The sites represented by Y are [C i H 2i-2 ] j1 , [C i H 2i ] j2 , [C 6 H 4 ] j3, [C i+1 H 2i-1 Cl] j4 , [C i H i Cl] j5, [ C5H4O3 ] j6 , [ C3H6N ] j7 , and [ C4H6O2N ]j8 , at least one
  • the present disclosure it is possible to provide a surface layer that has both stability of fixation during processing and antifouling properties, and an optical member and eyeglasses having the surface layer. Further, the present disclosure can provide a surface layer forming material that forms a surface layer that has both stability of fixation during processing and antifouling properties.
  • Schematic diagram showing the configuration of the surface layer in the first embodiment Schematic diagram showing the configuration of the surface layer in the second embodiment
  • Schematic diagram showing the configuration of an optical member in a second embodiment A schematic diagram showing the configuration of an embodiment of eyeglasses using optical members
  • a surface layer according to the present disclosure an optical member having the surface layer, eyeglasses having the optical member, and a material for forming the surface layer according to the present disclosure will be described by citing preferred embodiments. Further, the present disclosure is not limited to the embodiments below.
  • the descriptions such as "XX to YY" and “XX to YY” expressing a numerical range mean a numerical range including the lower limit and upper limit, which are the endpoints, unless otherwise specified. Furthermore, when numerical ranges are described in stages, the upper and lower limits of each numerical range can be arbitrarily combined.
  • slippage is suppressed by keeping the frictional force high when a high load is applied to the surface layer of the base material or the optical member, and when processing the base material or the optical member, the base material or the optical member is Can be stably fixed.
  • the frictional force is low and antifouling properties can be exhibited.
  • a material for forming a surface layer that imparts the above characteristics to the surface layer.
  • component A contained in the surface layer a compound having a siloxane moiety containing a siloxane bond is selected.
  • component B a compound having an organic moiety having at least one bond selected from the group consisting of a saturated hydrocarbon bond, an unsaturated hydrocarbon bond, a carbon-oxygen double bond, and a carbon-nitrogen double bond.
  • Component A which has a siloxane moiety containing a siloxane bond, exhibits antifouling properties, but tends to have low frictional force when a load is applied.
  • a siloxane bond is a bond consisting of a silicon atom and an oxygen atom, and is represented by the following chemical formula (1).
  • Si-O-Si...(1) Since the rotational energy of the silicon-oxygen bond in the above formula (1) is as small as 0.8 kJ/mol or less, the silicon-oxygen bond is characterized by easy movement.
  • component B has an organic moiety having at least one bond selected from the group consisting of a saturated hydrocarbon bond, an unsaturated hydrocarbon bond, a carbon-oxygen double bond, and a carbon-nitrogen double bond. Therefore, compared to component A, it is less likely to deform under load and tends to have higher frictional force. Therefore, when a surface layer containing at least component A and component B comes into contact with an object and a high load is applied, component A deforms but component B hardly deforms. As a result, a high frictional force can be obtained by increasing the proportion of component B in contact with the object that contacts the surface layer.
  • component B has an organic moiety having at least one bond selected from the group consisting of an unsaturated hydrocarbon bond, a carbon-oxygen double bond, and a carbon-nitrogen double bond
  • the load is not applied. This is preferable because it is less likely to deform and has a higher frictional force.
  • the composition ratio of component B to component A in the surface layer within a predetermined range, high antifouling properties can be obtained when the surface layer and an object come into contact with each other under low load.
  • “Surface layer” refers to an interface that is in contact with a base material and in contact with a solid, liquid, or gas. That is, in this specification, the “surface layer” is the surface of a base material, and this specification also discloses a base material having this surface. Any material can be used as the base material as long as it is solid and can form the base layer 12, surface layer 13, intermediate layer 14, or hard coat layer 15, which will be described later. Glass, ceramic, resin, etc. Alternatively, it is preferably a film made of metal, glass, resin, or the like.
  • the optical member is an optical member including a base material having the above-mentioned surface layer.
  • Examples of the optical member include optical filters, optical lenses, eyeglass lenses, photographic lenses, display cover glasses, display touch panels, and various films.
  • the glasses are glasses that have the optical member described above.
  • the glasses include all devices worn around the eyes, and are not limited to normal vision correction glasses, but include fancy glasses, protective goggles, head-mounted displays, sunglasses, smart glasses, and the like.
  • Component A has a siloxane moiety containing a siloxane bond.
  • the siloxane moiety containing the siloxane bond is preferably at least one moiety selected from the group consisting of a dimethylsiloxane moiety, a diphenylsiloxane moiety, a methylphenylsiloxane moiety, a methylhydrogensiloxane moiety, and a phenylhydrogensiloxane moiety. , a dimethylsiloxane site, a diphenylsiloxane site, and a methylphenylsiloxane site.
  • component A is, for example, the following general formula (2) R 1 -X-R 2 (2)
  • the site represented by X in formula (2) consists of any combination of at least one site selected from the sites shown in Table 1 below.
  • SiC 2 H 6 represents -Si(CH 3 ) 2 -
  • SiC 7 H 8 represents -Si(CH 3 ) Ph-
  • SiC 6 H 6 represents -SiHPh-
  • SiC 12 H 10 represents -Si(Ph) 2 -
  • SiCH 4 represents -Si(CH 3 )H-.
  • Ph represents a phenyl group.
  • m 1 , m 2 , m 3 , m 4 , and m 5 in Table 1 satisfy 2 ⁇ m 1 +m 2 +m 3 +m 4 +m 5 ⁇ 150.
  • a more preferable range of m 1 +m 2 +m 3 +m 4 +m 5 is 5 ⁇ m 1 +m 2 +m 3 +m 4 +m 5 ⁇ 120, and an even more preferable range is 10 ⁇ m 1 +m 2 +m 3 +m 4 +m 5 ⁇ 50.
  • m 1 , m 2 , m 3 , m 4 , and m 5 in Table 1 are each independently an integer of 0 or more. That is, m 1 , m 2 , m 3 , m 4 , and m 5 in Table 1 may be different values for each site.
  • m 1 , m 2 , m 3 , m 4 , and m 5 are 0, which means that each site listed in Table 1 is not included in the site indicated by X in formula (2). shows.
  • O in Table 1 represents oxygen constituting a siloxane bond.
  • R 1 and R 2 in general formula (2) are each independently a hydrolyzable group, a silanol group, a hydroxy group, a reactive organic group, an organic group containing a hydrolyzable group-containing silyl group, an alkylsilyl group, or A hydrogen atom is preferred.
  • hydrolyzable groups include alkoxy groups having 1 to 10 carbon atoms such as methoxy, ethoxy, propoxy, butoxy, alkoxyalkoxy groups having 2 to 10 carbon atoms such as methoxymethoxy and methoxyethoxy, and acetoxy groups.
  • Examples include acyloxy groups having 1 to 10 carbon atoms such as, alkenyloxy groups having 2 to 10 carbon atoms such as isopropenoxy, halogen groups such as chloro group, bromo group, and iodo group, and amino groups. Among these, methoxy, ethoxy, isopropenoxy, and chloro groups are preferred.
  • Examples of the reactive organic group include a methacrylic group, a carboxy group, an epoxy group, and a thiol group. Among these, methacrylic groups and carboxy groups are preferred.
  • the organic group containing a hydrolyzable group-containing silyl group is, for example, an organic group in which a hydrolyzable group is bonded directly or indirectly to a silicon atom.
  • hydrolyzable groups examples include alkoxy groups having 1 to 10 carbon atoms such as methoxy, ethoxy, propoxy, butoxy, alkoxyalkoxy groups having 2 to 10 carbon atoms such as methoxymethoxy and methoxyethoxy, and acetoxy groups.
  • examples include acyloxy groups having 1 to 10 carbon atoms such as, alkenyloxy groups having 2 to 10 carbon atoms such as isopropenoxy, halogen groups such as chloro group, bromo group, and iodo group, and amino groups.
  • the number of hydrolyzable groups in the organic group containing a hydrolyzable group-containing silyl group is preferably 1 to 3, more preferably 2 to 3, and still more preferably 3.
  • the organic group containing a hydrolyzable group-containing silyl group may have an alkylsilyl group described below. That is, examples of organic groups containing a hydrolyzable group-containing silyl group include trimethoxysilyl group, dimethoxymethylsilyl group, ethyldimethoxysilyl group, methoxydimethylsilyl group, diethylmethoxysilyl group, ethylmethoxymethylsilyl group, and triethoxysilyl group. group, diethoxyethylsilyl group, diethoxymethylsilyl group, ethoxydiethylsilyl group, ethoxyethylmethylsilyl group, and the like.
  • alkylsilyl group examples include alkylsilyl groups having 1 to 10 carbon atoms, and the number of carbon atoms in the alkylsilyl group is preferably 1 to 5, more preferably 1 to 3, and preferably 1. Particularly preferred.
  • the number of alkyl groups is preferably 1 to 3, more preferably 2 to 3, even more preferably 3. That is, examples of the alkylsilyl group include trimethylsilyl group, triethylsilyl group, ethyldimethylsilyl group, and diethylmethylsilyl group.
  • component A examples include, but are not limited to, the compounds shown in Table 2-1 and Table 2-2. Moreover, as component A, one type of compound having a siloxane moiety having a siloxane bond may be used alone, or two or more types may be used in combination. In Tables 2-1 and 2-2, SiC 2 H 6 represents -Si(CH 3 ) 2 -, SiC 7 H 8 represents -Si(CH 3 ) Ph-, and SiC 6 H 6 represents -Si(CH 3 ) Ph-.
  • SiC 12 H 10 represents -Si(Ph) 2 -
  • SiCH 4 represents -Si(CH 3 )H-
  • C 4 H 5 O 2 represents a methacrylic group.
  • Me represents a methyl group
  • Et represents an ethyl group
  • Ph represents a phenyl group.
  • Component B has an organic moiety having at least one bond selected from the group consisting of a saturated hydrocarbon bond, an unsaturated hydrocarbon bond, a carbon-oxygen double bond, and a carbon-nitrogen double bond.
  • component B has an organic moiety with an unsaturated hydrocarbon bond, and the unsaturated hydrocarbon bond is 1,2-polybutadiene, 1,4-polybutadiene, 1,2-polyisoprene, 1,4- It is derived from at least one compound selected from the group consisting of polyisoprene, 1,2-polychloroprene, and 1,4-polychloroprene.
  • the unsaturated hydrocarbon bond is derived from at least one compound selected from the group consisting of 1,2-polybutadiene and 1,2-polyisoprene.
  • the expression that the unsaturated hydrocarbon bond is derived from the above at least one compound means that the unsaturated hydrocarbon bond possessed by the organic moiety corresponds to the unsaturated hydrocarbon bond contained in the above at least one compound. shows.
  • component B has a polyolefin having an organic moiety in a side chain having at least one bond selected from the group consisting of an unsaturated hydrocarbon bond, a carbon-oxygen double bond, and a carbon-nitrogen double bond. This is also a preferred embodiment.
  • component B is, for example, represented by the following general formula (3) R 3 -Y-R 4 (3) It is an alkyl compound having the structure shown below.
  • R 3 -Y-R 4 (3) an alkyl compound having the structure shown below.
  • “an organic moiety having at least one bond selected from the group consisting of a saturated hydrocarbon bond, an unsaturated hydrocarbon bond, a carbon-oxygen double bond, and a carbon-nitrogen double bond” refers to the component
  • B is a compound having the structure represented by the above general formula (3), it is a moiety represented by Y in the above general formula (3).
  • the moiety represented by Y in the above general formula (3) is selected from the group consisting of a saturated hydrocarbon bond, an unsaturated hydrocarbon bond, a carbon-oxygen double bond, and a carbon-nitrogen double bond shown in Table 3. Contains one or more sites containing at least one selected bond. Furthermore, the saturated hydrocarbon bond, unsaturated hydrocarbon bond, carbon-oxygen double bond, and carbon-nitrogen double bond may have one or more bonds of any one type. , may have a combination of two or more types of bonds. In the table, C 6 H 4 represents a phenylene group.
  • i and j 1 , j 2 , j 3 , j 4 , j 5 , j 6 , j 7 and j 8 in Table 3 are 32 ⁇ i ⁇ (j 1 +j 2 +j 3 +j 4 +j 5 +j 6 +j 7 +j 8 ) ⁇ 750 is preferably satisfied, and 40 ⁇ i ⁇ (j 1 +j 2 +j 3 +j 4 +j 5 +j 6 +j 7 +j 8 ) ⁇ 180 is more preferably satisfied.
  • i in Table 3 is each independently an integer of 1 or more, and may be a different value for each site.
  • j 1 , j 2 , j 3 , j 4 , j 5 , j 6 , j 7 and j 8 in Table 3 are each independently an integer of 0 or more. That is, j 1 , j 2 , j 3 , j 4 , j 5 , j 6 , j 7 and j 8 in Table 3 may have different values for each site.
  • j 1 , j 2 , j 3 , j 4 , j 5 , j 6 , j 7 and j 8 are 0 if each moiety listed in Table 3 is Y in formula (3). Indicates that it is not included in the indicated region.
  • branching occurs in the middle of the molecular chain, saturated hydrocarbon bonds, unsaturated hydrocarbon bonds, carbon -
  • a side chain consisting of a site having at least one bond selected from the group consisting of an oxygen double bond and a carbon-nitrogen double bond may be present within the site indicated by Y.
  • C 5 H 4 O 3 refers to a bond formed by grafting maleic anhydride onto a part of the side chain of a polyolefin such as polyethylene or polypropylene.
  • C 3 H 6 N refers to a bond in which a part of the side chain of a polyolefin such as polyethylene or polypropylene is substituted with an amino group.
  • C 4 H 6 O 2 N refers to a bond in which a part of the side chain of a polyolefin such as polyethylene or polypropylene is substituted with an isocyanate group.
  • the moiety represented by Y in the above general formula (3) is selected from the group consisting of a saturated hydrocarbon bond, an unsaturated hydrocarbon bond, a carbon-oxygen double bond, and a carbon-nitrogen double bond shown in Table 4. It is preferable to include one or more sites containing at least one selected bond.
  • k 1 , k 2 , k 3 , k 4 , k 5 , k 6 , k 7 , k 8 , k 9 and k 10 in Table 4 are 8 ⁇ k 1 +k 2 +k 3 +k 4 +k 6 +k 7 +k It is preferable to satisfy 8 +k 9+ k 10 ⁇ 180, and more preferably to satisfy 40 ⁇ k 1 +k 2 +k 3 +k 4 +k 6 +k 7 +k 8 +k 9+ k 10 ⁇ 120.
  • k 1 , k 2 , k 3 , k 4 , k 5 , k 6 , k 7 , k 8 , k 9 and k 10 in Table 4 are each independently an integer of 0 or more.
  • k 1 , k 2 , k 3 , k 4 , k 5 , k 6 , k 7 , k 8 , k 9 and k 10 in Table 4 may have different values for each site.
  • k 1 , k 2 , k 3 , k 4 , k 5 , k 6 , k 7 , k 8 , k 9 and k 10 are 0 means that each moiety listed in Table 4 has the formula ( 3) Indicates that it is not included in the site indicated by Y.
  • branching occurs in the middle of the molecular chain, unsaturated hydrocarbon bonds, carbon-oxygen double bonds, and A side chain consisting of a moiety having at least one bond selected from the group consisting of carbon-nitrogen double bonds may be present within the moiety represented by Y.
  • component B is that any one or any combination of unsaturated hydrocarbon bonds, carbon-oxygen double bonds, and carbon-nitrogen double bonds are present on the side chain side. is preferred. More preferably, either an unsaturated hydrocarbon bond or a carbon-oxygen double bond, or any combination thereof, is present on the side chain side.
  • R 3 and R 4 in the above general formula (3) each independently represent a hydrolyzable group, a silanol group, a hydroxy group, a reactive organic group, an organic group containing a hydrolyzable group-containing silyl group, an alkylsilyl group or a hydrogen atom.
  • they are an organic group containing a hydrolyzable group-containing silyl group, a hydroxy group, and a hydrogen atom. More preferred is a hydroxy group or a hydrogen atom.
  • hydrolyzable groups include alkoxy groups having 1 to 10 carbon atoms such as methoxy, ethoxy, propoxy, butoxy, alkoxyalkoxy groups having 2 to 10 carbon atoms such as methoxymethoxy and methoxyethoxy, and acetoxy groups.
  • alkoxy groups having 1 to 10 carbon atoms such as methoxy, ethoxy, propoxy, butoxy, alkoxyalkoxy groups having 2 to 10 carbon atoms such as methoxymethoxy and methoxyethoxy, and acetoxy groups.
  • acyloxy groups having 1 to 10 carbon atoms such as, alkenyloxy groups having 2 to 10 carbon atoms such as isopropenoxy, halogen groups such as chloro group, bromo group, and iodo group, and amino groups.
  • methoxy, ethoxy, isopropenoxy, and chloro groups are preferred.
  • Examples of the reactive organic group include a methacrylic group, a carboxy group, an epoxy group, and a thiol group. Among these, methacrylic groups and carboxy groups are preferred.
  • the organic group containing a hydrolyzable group-containing silyl group is, for example, an organic group in which a hydrolyzable group is bonded directly or indirectly to a silicon atom.
  • Examples of hydrolyzable groups include alkoxy groups having 1 to 10 carbon atoms such as methoxy, ethoxy, propoxy, butoxy, alkoxyalkoxy groups having 2 to 10 carbon atoms such as methoxymethoxy and methoxyethoxy, and acetoxy groups.
  • Examples include acyloxy groups having 1 to 10 carbon atoms such as, alkenyloxy groups having 2 to 10 carbon atoms such as isopropenoxy, halogen groups such as chloro group, bromo group, and iodo group, and amino groups.
  • the number of hydrolyzable groups in the organic group containing a hydrolyzable group-containing silyl group is preferably 1 to 3, more preferably 2 to 3, and still more preferably 3.
  • the organic group containing a hydrolyzable group-containing silyl group may have an alkylsilyl group described below.
  • organic groups containing a hydrolyzable group-containing silyl group include trimethoxysilyl group, dimethoxymethylsilyl group, ethyldimethoxysilyl group, methoxydimethylsilyl group, diethylmethoxysilyl group, ethylmethoxymethylsilyl group, and triethoxysilyl group. group, diethoxyethylsilyl group, diethoxymethylsilyl group, ethoxydiethylsilyl group, ethoxyethylmethylsilyl group, and the like.
  • alkylsilyl group examples include alkylsilyl groups having 1 to 10 carbon atoms, and the number of carbon atoms in the alkylsilyl group is preferably 1 to 5, more preferably 1 to 3, and preferably 1. Particularly preferred.
  • the number of alkyl groups is preferably 1 to 3, more preferably 2 to 3, even more preferably 3. That is, examples of the alkylsilyl group include trimethylsilyl group, triethylsilyl group, ethyldimethylsilyl group, and diethylmethylsilyl group.
  • component B examples include the compounds shown in Table 5, but are not limited to these compounds.
  • one or more sites containing at least one bond selected from the group consisting of a saturated hydrocarbon bond, an unsaturated hydrocarbon bond, a carbon-oxygen double bond, and a carbon-nitrogen double bond are used as component B. These compounds may be used alone or in combination of two or more.
  • component B includes the compounds shown in Table 6, but are not limited to these compounds.
  • the compounds shown in Table 6 are alkyl compounds having either a saturated hydrocarbon bond, an unsaturated hydrocarbon bond, a carbon-oxygen double bond, or a carbon-nitrogen double bond, from d-1 to d- 4 is a modified polyolefin in which part of the side chain is replaced with a different site.
  • sites to be replaced include imino sites, vinyl sites, carboxylic acid sites, carboxylic anhydride sites, ketene sites, isocyanate sites, and the like.
  • composition ratio of component B to component A in the surface layer of the present disclosure is such that when the surface layer is measured using a micro-Raman spectrometer, P A is the peak intensity derived from component A, and P B is the peak intensity derived from component B. It is expressed as P B /P A , and can be expressed in the range of 0.04 to 3.00. Further, the composition ratio of component B to component A in the surface layer of the present disclosure can be adjusted by the mass ratio of component B to component A in the surface layer forming material of the present disclosure. The composition ratio is preferably 0.10 to 1.00, more preferably 0.20 to 0.60.
  • composition ratio of component B to component A is less than 0.04, antifouling properties will be exhibited, but the frictional force will not increase when a high load is applied during processing, and slipperiness will not be suppressed, making it difficult to process the base material. It becomes difficult. Furthermore, if the composition ratio of component B to component A is greater than 3.00, not only will the antifouling properties deteriorate, but also the frictional force will be high even under the load range that users use on a daily basis, making it difficult to wipe off dirt. There are some problems with ease of use, such as the cloth getting caught.
  • the composition ratio of component B to component A can be determined by the following method. First, a region of the surface layer to be measured with a micro Raman spectrometer is determined. The area is determined by the magnification of the objective lens attached to the device, the wavelength of the excitation laser, and the aperture diameter. Hereinafter, the determined area will also be referred to as a "measurement area.” Next, the measurement area is irradiated with excitation laser light and the generated scattered light is measured to obtain a Raman spectrum. The measurement conditions are as follows.
  • ⁇ Measurement device Micro Raman spectrometer manufactured by Thermo Fisher Scientific ⁇ Objective lens magnification: 10x ⁇ Excitation laser wavelength: 532 nm ⁇ Aperture diameter: 25 ⁇ m ⁇ Measurement area: 2 ⁇ m Among the peaks in the obtained Raman spectrum, the peak originating from the siloxane bond is defined as the peak originating from component A, and the peak intensity of the peak is defined as PA .
  • X be the frictional force measured when the load on the surface layer is 14 kgf and the friction speed is 2.5 mm/sec
  • the rate of change in frictional force expressed as (YX)/X ⁇ 100 is preferably 50% to 200%, more preferably 80% to 140%.
  • the rate of change can be controlled by the type of component A, the type of component B, and the composition ratio of component B to component A.
  • the surface layer of the present disclosure may contain any compound other than component A and component B as long as the effects of the present disclosure are not impaired.
  • FIG. 1 is a schematic diagram showing the structure of the surface layer in a first embodiment, and shows an example of a structure in which a base layer is formed on a base material and a surface layer is formed on the base layer.
  • a base layer 12 exists on a base material 11, and a surface layer 13 is formed on the base layer 12.
  • FIG. 1 is a simulated representation of a configuration having a surface layer, and does not represent the actual thicknesses of the base material 11, base layer 12, and surface layer 13 in accurate ratios.
  • the base material 11 may be any material as long as it is a solid material and can form the base layer 12, the surface layer 13, or the intermediate layer 14 or hard coat layer 15 described below, such as glass, ceramic, resin, metal, or glass. Examples include films made from resin and other materials.
  • the base material is capable of transmitting visible light or light of a specific wavelength.
  • the thickness of the base material is not particularly limited and can be set as appropriate depending on the application.
  • the base layer 12 is a layer that serves as a base for forming the surface layer 13 and improves the adhesion between the base material 11 and the surface layer 13.
  • a base layer 12 is formed on the base material 11, and a surface layer 13 is formed on the base layer 12.
  • the method for forming the base layer is not particularly limited, and examples thereof include a vapor deposition method, a dipping method, a coating method, a spray method, and a spin coating method.
  • the thickness of the base layer 12 is not particularly limited, but is 2 nm to 150 nm, preferably 5 nm to 125 nm.
  • the material forming the base layer 12 is preferably a substance that has hydroxyl groups on its surface. Examples include metal oxides such as SiO 2 and Al 2 O 3 that have hydroxy groups on their surfaces, and alkyl compounds that have hydroxy groups.
  • the surface layer 13 is a surface layer of component A and component B of the present disclosure.
  • the thickness of the surface layer 13 is not particularly limited, but is preferably 4 nm to 20 nm. When the thickness is 4 nm or more, sufficient antifouling properties are obtained, and when the thickness is 20 nm or less, transparency is good.
  • the method for forming the surface layer is not particularly limited, and examples include a vapor deposition method and a coating method. Further, examples of coating methods include spin coating, dip coating, bar coating, and spray coating.
  • a surface layer of component A and component B can be formed.
  • the surface layer is a vapor deposited layer.
  • the surface layer is a coating layer.
  • FIG. 2 is a schematic diagram showing the structure of a second embodiment of the surface layer, in which an intermediate layer is formed on a base material, a base layer is formed on the intermediate layer, and a base layer is formed on the base layer.
  • An example of a structure having a surface layer is shown below.
  • an intermediate layer 14 is formed on a base material 11, in which intermediate layers 14a and 14c having a low refractive index material and intermediate layers 14b and 14d having a high refractive index material are alternately laminated.
  • a surface layer 13 is formed on the base layer 12 provided on the intermediate layer 14.
  • FIG. 2 is a simulated representation of the structure of the surface layer, and does not represent the actual thicknesses of the base material 11, intermediate layer 14, base layer 12, and surface layer 13 in accurate ratios.
  • the odd-numbered intermediate layers 14a and 14c laminated from the base material 11 side are made of a low refractive index material, and the even-numbered intermediate layers 14b and 14d are laminated from a low refractive index material.
  • the base layer 12 is also made of a low refractive index material, is laminated on the intermediate layer 14, and exhibits an antireflection function together with the intermediate layer 14.
  • the intermediate layer 14 has four layers, and since the base layer 12 is formed on the intermediate layer 14d having a high refractive index material, the base layer 12 can be made of a low refractive index material. preferable.
  • the intermediate layer 14 has three layers and the base layer 12 is formed on the intermediate layer 14b having a high refractive index material, it is preferable that the base layer 12 is made of a low refractive index material. Further, the intermediate layer 14 is not limited to this embodiment, and layers made of medium refractive index materials may be laminated as appropriate.
  • Examples of the low refractive index material include SiO 2 (silicon dioxide), Al 2 O 3 -doped SiO 2 (alumina-doped silicon dioxide), and the like. However, the low refractive index material is not limited to these materials.
  • Examples of high refractive index materials include alumina-containing titanium oxide-lanthanum oxide mixed materials, titanium oxide, other mixed oxides containing titanium oxide as the main component, zirconium oxide, mixed materials containing zirconium oxide as the main component, niobium oxide, Examples include a mixed material containing niobium oxide as a main component, tantalum oxide, a mixed material containing tantalum oxide as a main component, tungsten oxide, and a mixed material containing tungsten oxide as a main component.
  • the high refractive index material is not limited to this.
  • the medium refractive index material include aluminum oxide, other mixed compounds containing aluminum oxide as a main component, magnesium oxide, other mixed compounds containing magnesium oxide as a main component, yttrium fluoride, and cerium fluoride.
  • the medium refractive index material is not limited to this.
  • the thickness of the intermediate layer 14 and each layer (14a, 14b, 14c, 14d in FIG. 2) constituting the intermediate layer 14 is 10 nm to 200 nm
  • the intermediate layer 14 can be constructed by laminating a required number of layers. Note that although the intermediate layer 14 in this embodiment has a four-layer configuration, the present disclosure is not limited to this at all, and the number of layers may be any number.
  • the intermediate layer 14 is provided as a part of the antireflection film formed by laminating the low refractive index layer and the high refractive index layer alternately, but the present disclosure does not include the intermediate layer 14. It is not limited in any way. For example, at least one layer having a function selected from other filters, mirrors, antistatic hard coats, anti-scratch hard coats, etc. may be formed between the base material 11 and the intermediate layer 14.
  • base material, base layer, and surface layer in the second embodiment of the surface layer can be the same as those in the first embodiment of the surface layer.
  • FIG. 3 is a schematic diagram showing the configuration of the optical member in the first embodiment.
  • This embodiment is an optical member that can be used for eyeglass lenses.
  • the optical member in FIG. 3 includes a base material 11 made of resin, a hard coat layer 15 for preventing scratches, an intermediate layer 14 having the antireflection function described in the second embodiment of the surface layer, and a base layer 12. and a surface layer 13 are provided.
  • the intermediate layer 14 the odd-numbered intermediate layer 14a laminated from the base material 11 side is made of a low refractive index material
  • the even-numbered intermediate layer 14b laminated is a two-layer layer made of a high refractive index material.
  • the structure is not limited to this, and the number of layers may be any number.
  • layers made of medium refractive index material may be laminated as appropriate.
  • the hard coat layer 15 for example, melamine resin, urethane resin, acrylic resin, a mixture of the above resins, a silane compound, etc. can be used.
  • the material used for the hard coat layer is not limited to this.
  • the optical member shown in the configuration in the first embodiment is not limited to spectacle lenses, and can be used for other known purposes.
  • FIG. 4 is a schematic diagram showing the configuration of the optical member in the second embodiment.
  • This embodiment is an optical member that can be used in an optical lens used in a camera or the like.
  • the optical member in FIG. 4 is provided with a base material 11 made of glass, an intermediate layer 14 having the antireflection function described in the second embodiment of the surface layer, a base layer 12, and a surface layer 13.
  • the intermediate layer 14 the odd-numbered intermediate layer 14a laminated from the base material 11 side is made of a low refractive index material
  • the even-numbered intermediate layer 14b laminated is a two-layered layer made of a high refractive index material.
  • the structure is not limited to this, and the number of layers may be any number.
  • optical member shown in the configuration of the second embodiment is not limited to those used in optical lenses for cameras, but can also be used in optical filters, touch panels for displays, various films, and the like.
  • FIG. 5 is a schematic diagram showing the configuration of an embodiment of eyeglasses using the optical member of the present disclosure.
  • the present embodiment is composed of a spectacle lens 31, which is the optical member of the present disclosure described above, and a spectacle frame 32.
  • the surface layer forming material of the present disclosure is a surface layer forming material containing at least component A and component B,
  • the component A has a siloxane moiety containing at least a siloxane bond
  • Component B has an organic moiety having at least one bond selected from the group consisting of a saturated hydrocarbon bond, an unsaturated hydrocarbon bond, a carbon-oxygen double bond, and a carbon-nitrogen double bond, and the following general formula (3) R 3 -Y-R 4 (3)
  • An alkyl compound having the structure shown in The sites represented by Y are [C i H 2i-2 ] j1 , [C i H 2i ] j2 , [C 6 H 4 ] j3, [C i+1 H 2i-1 Cl] j4 , [C i H i Cl] j5, [ C5H4O3 ] j6 , [ C3H6N ] j7 , and [ C4H6O2N ]j8 , at least
  • the surface layer forming material according to the present disclosure will be explained.
  • Component A and component B constituting the surface layer forming material of the present disclosure are the same as component A and component B constituting the surface layer of the present disclosure.
  • the mass ratio of component A to component B in the surface layer forming material of the present disclosure is such that when the mass of component A is 1, the mass of component B is in the range of 0.04 to 3.00. That is, the mass ratio of component B to component A in the surface layer forming material is 0.04 to 3.00.
  • the mass ratio is preferably 0.10 to 1.00, more preferably 0.20 to 0.60.
  • the surface layer formed using the surface layer forming material exhibits antifouling properties, but the processing of the base material or optical member having the surface layer is Sometimes, when a high load is applied, the frictional force does not increase and the slipperiness is not suppressed, making it difficult to process the base material or optical member.
  • the mass ratio of component B to component A is greater than 3.00, the frictional force will be high even in the range of loads that users use on a daily basis, and the surface layer formed using the surface layer forming material will be Not only does the antifouling property deteriorate, but the cloth also gets stuck when wiping away dirt, making it difficult to use.
  • the mass ratio of component B to component A in the surface layer forming material can be determined using liquid chromatography mass spectrometry. Alternatively, it can also be determined using the values of the mass of component A and the mass of component B, which were weighed on a balance when producing the material for forming the surface layer.
  • the surface layer forming material according to the present disclosure is not particularly limited as long as the mass ratio of component B to component A in the surface layer forming material is in the range of 0.04 to 3.00, and may contain other materials. You can also do it.
  • the material for forming the surface layer may be solid or liquid. For example, it is also possible to dissolve component A and component B in an organic solvent such as hexane or toluene to form a liquid solution.
  • the surface forming material is a liquid, the surface layer can be formed by a coating method.
  • the surface forming material may contain an organic solvent.
  • Organic solvents are not particularly limited, but include, for example, ketone solvents such as acetone and methyl ethyl ketone; ether solvents such as dimethyl ether, diethyl ether, and tetrahydrofuran; aromatic hydrocarbon solvents such as benzene, toluene, chlorobenzene, and xylene; and isohexane ( At least one solvent selected from the group consisting of aliphatic hydrocarbon solvents such as 2-methylpentane), 3-methylpentane, 2,2-dimethylbutane and 2,3-dimethylbutane, n-hexane, heptane, and cyclohexane. can be mentioned.
  • the content of the organic solvent is not particularly limited, but can be, for example, 50 to 150 parts by mass, when the total content of component A and component B in the surface layer forming material is 100 parts by mass.
  • Example 1 (Preparation of surface layer forming material)
  • the compound (A-3) listed in Table 2-1 as Component A and the compound (a-3) listed in Table 5 as Component B were combined in a mass ratio of Component B to Component A of 0.20.
  • the mixture was mixed in a metal container to obtain Surface Layer Forming Material 1.
  • a base layer 12 made of SiO 2 and having a thickness of 10 nm was formed on a 3 mm thick borosilicate glass serving as the base material 11 by a vapor deposition method using a vacuum vapor deposition apparatus (dome diameter ⁇ 900 mm, vapor deposition distance 890 mm).
  • the thickness of the base layer 12 was measured using spectroscopic ellipsometry (manufactured by JA WOOLLAM - ESM300).
  • a surface layer 13 of the present disclosure made of the surface layer forming material 1 is formed on the base layer 12 by a vapor deposition method using a vacuum vapor deposition apparatus (dome diameter ⁇ 900 mm, vapor deposition distance 890 mm), The member was manufactured.
  • the thickness of the surface layer 13 was measured using spectroscopic ellipsometry (manufactured by JA WOOLLAM - ESM300) and was found to be 10 nm.
  • the composition ratio of component B to component A in the obtained surface layer was measured using a micro-Raman spectrometer, it was found to be 0.20, which is the same as the mass ratio of component B to component A in the surface layer forming material.
  • the structure of the obtained optical member is similar to the structure of the optical member having the surface layer of the present disclosure shown in FIG.
  • the frictional force of the surface layer was measured according to the following method.
  • a device for measuring the frictional force an automatic friction and wear analysis device Triboster 500 manufactured by Kyowa Interface Science Co., Ltd. was used.
  • a rubber pad (lens blocking pad manufactured by 3M) cut to 2 mm 2 was used as a contact for measuring the frictional force, and the frictional force was measured by bringing the rubber pad into contact with the surface layer of the optical member.
  • the test was conducted by adjusting the applied load of the device so that the load applied to the surface layer was 14 kgf and 70 kgf.
  • the friction speed was 2.5 mm/sec.
  • Table 7-1 The results are shown in Table 7-1.
  • the antifouling properties of the surface layer of the produced optical member were evaluated according to the following method. As indicators of antifouling properties, evaluation was performed based on the following criteria, using the ink repellency of the highlighter pen and the ease of wiping it off. The results are shown in Table 7-1.
  • evaluation criteria A: After attaching the pen tip to the surface layer, the ink becomes spherical and repelled over 1 to 5 seconds, and can be wiped off with lint paper.
  • B After the pen tip was attached to the surface layer, the ink was not repelled even after 5 seconds and could not be wiped off unless rubbed strongly with lint paper.
  • Examples 2 to 214 The compounds listed in Tables 2-1 and 2-2 used as component A, the compounds listed in Tables 5 and 6 used as component B, and the composition ratio of component B to component A after surface layer formation. , Table 7-2, Table 8-1 and Table 8-2, respectively, were prepared in the same manner as in Example 1 except for the following changes: After producing a material for forming a surface layer, a base layer and a surface layer were formed to produce an optical member having a surface layer according to the present disclosure. Further, in the same manner as in Example 1, frictional force and antifouling performance were evaluated. The results are shown in Table 7-1, Table 7-2, Table 8-1 and Table 8-2. In addition, in Examples 2 to 214, similarly to Example 1, the composition ratio of component B to component A in the obtained surface layer and the mass ratio of component B to component A in the surface layer forming material were the same. was.
  • Example 215 The optical member (glass lens) produced in the same manner as in Example 5 was processed and attached to a commercially available frame to produce eyeglasses. As in Example 1, the frictional force and antifouling performance of the optical members of the manufactured glasses were evaluated. The results are shown in Table 7-1.
  • Example 216 (Preparation of surface layer forming material)
  • the compound (A-3) listed in Table 2-1 as Component A and the compound (a-3) listed in Table 5 as Component B were mixed in such a manner that the mass ratio of Component B to Component A was 0.30.
  • After mixing in a glass container so that Component A and Component B are present add isohexane (product name: isohexane, manufactured by Tokyo Kasei Kogyo Co., Ltd.) in an amount equal to the total weight of Component A and Component B.
  • the mixture was poured into a glass container, and the mixture in the glass container was stirred until component A and component B could no longer be visually confirmed to obtain surface layer forming material 2.
  • An optical member having a surface layer of the present disclosure is obtained by coating the surface layer forming material 2 on a borosilicate glass having a thickness of 3 mm, which is the base material 11, using a bar coater and drying it at 25° C. for 24 hours. was created. Further, in the same manner as in Example 1, frictional force and antifouling performance were evaluated. The results are shown in Table 7-1. In addition, in Example 216, as in Example 1, the composition ratio of component B to component A in the obtained surface layer and the mass ratio of component B to component A in the surface layer forming material were the same. .
  • Base material 12 Foundation layer 13 Surface layer 14 Intermediate layer 14a, 14c Intermediate layer having a low refractive index material 14b, 14d Intermediate layer having a high refractive index material 15 Hard coat layer 31 Eyeglass lens 32 Eyeglass frame

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Health & Medical Sciences (AREA)
  • Ophthalmology & Optometry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Eyeglasses (AREA)
  • Surface Treatment Of Optical Elements (AREA)
  • Laminated Bodies (AREA)
PCT/JP2023/002999 2022-07-22 2023-01-31 表面層、光学部材、眼鏡、及び表面層形成用材料 Ceased WO2024018654A1 (ja)

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DE112023003193.2T DE112023003193T5 (de) 2022-07-22 2023-01-31 Oberflächenschicht, optisches element, brille und material zur herstellung von oberflächenschicht
JP2024098225A JP2024120006A (ja) 2022-07-22 2024-06-18 表面層、光学部材、及び眼鏡
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