JP2013186349A - Optical element manufacturing method - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an optical element manufacturing method which can manufacture an optical element having a hard coat layer of a uniform thickness in a use area of a spectacle lens, without requiring time and effort.SOLUTION: The optical element manufacturing method includes: supplying a hard coat layer-forming material in a liquid state for forming a hard coat layer 4, with a concave curved surface 61 of a lens base material 6 oriented vertically upward, so as to cover the concave curved surface 61; inverting the concave curved surface 61 of the lens base material 6 to orient it vertically downward; and heating the hard coat layer-forming material to form the hard coat layer 4.

Description

  The present invention relates to a method for manufacturing an optical member.

For example, as a plastic lens used for spectacles or the like, a lens having a high refractive index has been actively researched and developed in recent years in order to realize a reduction in thickness.
A plastic lens is advantageous in that it is lighter and more workable than a conventional glass lens, and exhibits a relatively high strength against impact. On the other hand, it has a disadvantage that it is inferior in friction resistance and weather resistance than a glass lens due to its low hardness.

Therefore, in particular, when a plastic lens is applied to a spectacle lens, it is generally performed to form a cured film called a hard coat layer on the plastic lens.
Furthermore, when a plastic lens is applied to a spectacle lens, an antireflection layer is generally formed on the hard coat layer. However, if the refractive index difference between the antireflection layer and the hard coat layer is too large, interference fringes are formed. Therefore, a material having a high refractive index is required as a constituent material of the hard coat layer.

As a hard coat layer realizing such a high refractive index, for example, a hard coat layer formed using a hard coat material containing an organosilicon compound (silane coupling agent) and a metal oxide is known.
More specifically, after preparing a hard coat layer forming material containing an organosilicon compound or a hydrolyzate thereof and a metal oxide (composite oxide sol), and supplying the hard coat material onto a plastic lens A sol-gel method is known in which a hard coat layer is obtained by gelation by heating.

Moreover, in the spectacle lens provided with such a hard coat layer, the cause of the occurrence of the above-mentioned interference fringes may be that a hard coat layer having a non-uniform film thickness is formed. For this purpose, as shown in Patent Document 1, there has been proposed a method of forming a hard coat layer with a uniform film thickness in an eyeglass lens use region.
In the method described in Patent Document 1, a hard coat layer is formed in advance on a sample under a certain film formation condition, and the film thickness of the formed hard coat layer is used as a database. A relationship is obtained, and a hard coat layer is formed on the spectacle lens based on the obtained relationship.
However, in this method, in order to create a database showing the relationship between the film formation conditions and the film thickness, it is necessary to form a hard coat layer for a plurality of samples and obtain the relationship between the film formation conditions and the film thickness There is a problem that it takes time and labor.

JP 2000-33021 A

  An object of the present invention is to provide an optical member manufacturing method capable of manufacturing an optical member in which a hard coat layer having a uniform film thickness is formed in a use region of an eyeglass lens without requiring time and labor. It is in.

Such an object is achieved by the present invention described below.
The method for producing an optical member of the present invention includes:
With the curved concave surface of the lens base material vertically upward, supplying a hard coat layer forming material that forms a liquid for forming a hard coat layer so as to cover the curved concave surface;
Reversing the curved concave surface of the lens base material vertically downward;
Heating the hard coat layer forming material to form the hard coat layer.

  When the liquid hard coat layer forming material is applied with the curved concave surface vertically upward, and the lens substrate is inverted, the hard coat layer forming material flows down the curved concave surface. Thereby, the film thickness of the center part of the lens for which appropriate optical performance is required as spectacles becomes uniform. Therefore, it is possible to manufacture an optical member in which a hard coat layer having a uniform film thickness is formed in the eyeglass lens use region without requiring time and labor.

In the method of manufacturing an optical member of the present invention, after the reversing step, the hard coat layer forming material flows down the curved concave surface that is vertically downward, and stays at the edge of the curved concave surface, whereby the hard coat The layer is preferably formed with a thick film portion whose thickness is thicker at the edge than at the center.
Thereby, the optical member in which the hard coat layer having a uniform film thickness is formed in the use region of the spectacle lens can be manufactured without requiring time and labor.

In the method for producing an optical member of the present invention, the supplying is preferably performed using a spray coating method.
The spray coating method is suitable for forming a hard coat layer having a relatively thick film thickness, and further, a liquid hard coat layer forming material can be uniformly supplied to the curved concave surface that is directed vertically upward. .

In the method for producing an optical member of the present invention, the hard coat layer forming material is represented by the general formula (1): (R ¹ ) _n Si (X ¹ ) _4-n (in the general formula (1), R ¹ is polymerizable). An organic group having 2 or more carbon atoms having a functional group, X ¹ represents a hydrolyzable group, and n represents an integer of 1 or 2.) is dissolved in a solvent. It is preferable.
The method for producing an optical member of the present invention is more suitably applied when the hard coat layer forming material is a sol.
In the method for producing an optical member of the present invention, it is preferable that the hard coat layer has an average thickness at the center of 5.0 μm or more and 50 μm or less.
When a hard coat layer having a film thickness in such a range is formed, a thick film portion is particularly formed in the hard coat layer.

In the method for producing an optical member of the present invention, the lens base material includes a curved convex surface facing the curved concave surface,
Prior to the heating step, it is preferable that a hard coat layer forming material for forming the hard coat layer is supplied to the curved convex surface of the lens substrate.
Accordingly, an optical member in which a hard coat layer having a uniform film thickness is formed on both the curved concave surface and the curved convex surface in the use region of the spectacle lens can be manufactured without requiring time and labor.

It is a figure which shows 1st Embodiment which applied the optical member manufactured by the manufacturing method of the optical member of this invention to the spectacles lens. It is a longitudinal cross-sectional view for demonstrating 1st Embodiment of the manufacturing method of the spectacle lens to which the manufacturing method of the optical member of this invention is applied. It is a figure which shows 2nd Embodiment which applied the optical member manufactured by the manufacturing method of the optical member of this invention to the spectacles lens. It is a longitudinal cross-sectional view for demonstrating 2nd Embodiment of the manufacturing method of the spectacle lens to which the manufacturing method of the optical member of this invention is applied.

Hereinafter, the manufacturing method of the optical member of this invention is demonstrated in detail based on suitable embodiment shown to an accompanying drawing.
Hereinafter, a case where the optical member manufactured by the method for manufacturing an optical member of the present invention is applied to a spectacle lens attached to spectacles will be described as an example.
First, before describing the method for manufacturing an optical member of the present invention, a first embodiment of a spectacle lens manufactured by applying the method for manufacturing an optical member of the present invention will be described.

<First Embodiment>
1A and 1B show a first embodiment in which an optical member manufactured by the method for manufacturing an optical member of the present invention is applied to a spectacle lens ((a) a plan view, (b) A shown in FIG. 1 (a). -A line sectional view). In the following, the object side of the eyeglass lens in FIG. 1B (the side closer to the object that is relatively visible when the eyeglass lens is worn) is referred to as “upper”, and the eyeball side of the eyeglass lens (the eyeglasses) When the lens is worn, the side that is relatively close to the eyeball) is called “lower”. Further, in FIG. 1, for convenience of explanation, the size and thickness of members constituting the spectacle lens are schematically shown exaggerated, and the size and thickness of each member are larger than the actual size. Different.

As shown in FIG. 1, the spectacle lens 1 is a plastic lens attached to spectacles, and is formed so as to cover the lens base 6 having the curved concave surface 61 and the curved convex surface 62 and the curved concave surface 61 of the lens base 6. The hard coat layer 4 is provided.
In this embodiment, the lens substrate 6 is made of plastic, and has a base material 2 having a curved concave surface 21 and a curved convex surface 22, and a primer layer 3 formed so as to cover the curved concave surface 21 of the base material 2. doing.

The base material 2 is made of plastic and serves as a base material (base material) of the eyeglass lens 1.
As shown in FIG. 1, the base material 2 has a perfect circle shape in a plan view, the lower surface is configured by a curved concave surface 21, and the upper surface is configured by a curved convex surface 22. The curved convex surface 22 constitutes a transmission surface through which light is transmitted.

  Examples of the constituent material of the base material 2 include, for example, methyl methacrylate homopolymer, copolymer having methyl methacrylate and one or more other monomers as monomer components, diethylene glycol bisallyl carbonate homopolymer, diethylene glycol bisallyl carbonate, Copolymers containing one or more other monomers as monomer components, sulfur-containing copolymers, halogen-containing copolymers, polycarbonate, polystyrene, polyvinyl chloride, unsaturated polyester, polyethylene terephthalate, polyurethane, polythiourethane, Homopolymer of monomer having sulfide bond, copolymer having sulfide and one or more other monomers as monomer components, copolymer having polysulfide and one or more other monomers as monomer components, polydisulfide And one kind Copolymers thereof to the other monomer above monomer component.

When a material having a relatively high refractive index of about 1.6 or more is used as a constituent material of the base material 2, the eyeglass lens 1 is composed of the primer layer 3 and the hard coat layer as in this embodiment. 4, the spectacle lens 1 can be appropriately suppressed or prevented from generating interference fringes.
The primer layer 3 is formed so as to cover the curved concave surface 21 of the base material 2, and is thereby laminated between the base material 2 and the hard coat layer 4. This is to ensure the adhesion and to exhibit a function for improving the impact resistance of the base material 2.

In the present embodiment, the lower surface of the primer layer 3 is also provided so as to follow the shape of the curved concave surface 21 of the base material 2 and constitutes the curved concave surface 61.
Examples of the constituent material of the primer layer 3 include acrylic resins, melamine resins, urethane resins, epoxy resins, polyvinyl acetal resins, amino resins, polyester resins, polyamide resins, vinyl alcohol resins, styrene. And resin materials such as resin, silicone resin, and mixtures or copolymers thereof. Among these, urethane resins and polyester resins are preferable. Thereby, the adhesiveness of the base material 2 and the hard-coat layer 4, and the primer layer 3 can be improved.

The primer layer 3 may further contain a metal oxide in addition to the resin material. Thereby, the refractive index of the primer layer 3 can be made higher, and the primer layer 3 can have a refractive index of a desired height by setting the content thereof.
Although it does not specifically limit as a metal oxide, For example, the oxide of Si, Al, Sn, Sb, Ta, Ce, La, Fe, Zn, W, Zr, In, Ti is mentioned, Among such oxides These can be used alone or in combination of two or more. The metal oxide may be a sol made of metal oxide fine particles.

Moreover, although the average thickness of the primer layer 3 is not specifically limited, It is preferable that it is 300-1000 nm, and it is more preferable that it is 500-700 nm.
The formation of the primer layer 3 can be omitted depending on the combination of the base material 2 and the hard coat layer 4. That is, the lens base 6 can be constituted by the base material 2 alone.

The hard coat layer 4 is provided so as to cover the curved concave surface 61 which is the lower surface of the lens substrate 6 (primer layer 3), and has a function for improving the friction resistance and weather resistance of the base material 2. is there.
In this invention, since this hard-coat layer 4 is manufactured with the manufacturing method (sol-gel method) of the optical member of this invention mentioned later, the film thickness in the edge becomes thicker than the film thickness in the center part. That is, the thick film portion 5 having a thickness larger than that of the central portion is formed at the edge portion.

However, since the hard coat layer 4 is formed with a uniform film thickness in the center portion on the center side of the thick film portion 5 and the thick film portion 5 is formed outside the use region of the spectacle lens, It is possible to reliably prevent interference fringes from occurring in the use region.
The hard coat layer 4 is formed using a composition (hard coat material) containing an organosilicon compound (silane coupling agent) and a metal oxide.

The organic silicon compound is not particularly limited, for example, the general formula _{^{(1) :( R 1) n}} Si in (X _{1) 4-n} (general formula (1), ^{R 1} has a polymerizable functional group An organic group having 2 or more carbon atoms, X ¹ represents a hydrolyzable group, and n represents an integer of 1 or 2 is used. Thereby, the organic silicon compound with each other is to be crosslinked via a functional group R ¹ (coupling), the hard coat layer 4 is made to exhibit excellent abrasion resistance and weather resistance.

The details of the organosilicon compound represented by the general formula (1) will be described in a method for manufacturing a spectacle lens described later (a method for manufacturing an optical member of the present invention).
The metal oxide contained in the hard coat layer 4 is not particularly limited, and examples thereof include metal oxides such as Al, Ti, Sb, Zr, Si, Ce, Fe, In, and Sn. One or two or more of oxides can be used in combination. Among these, in _{particular, TiO 2, ZrO 2, CeO} 2, ZnO 2, SnO 2 and ITO - is preferably (indium tin composite oxide). By adopting a configuration in which these metal oxides are included in the hard coat layer 4, the refractive index of the hard coat layer 4 can be set to be relatively high. Therefore, the base material 2 having a high refractive index is used. It can also be applied.

  The average thickness at the center of the hard coat layer 4 is preferably set to 5.0 μm or more and 20 μm or less, more preferably 10 μm or more and 25 μm. Thereby, the hard coat layer 4 has excellent strength. Further, when forming the hard coat layer 4 having a film thickness in such a range, a thick film portion is formed in the hard coat layer 4 particularly in the method for manufacturing the eyeglass lens 1 described later.

When a material having a relatively high refractive index of about 1.6 or more is used as a constituent material of the base material 2, the eyeglass lens 1 is composed of the primer layer 3 and the hard coat layer as in this embodiment. 4, the spectacle lens 1 can be appropriately suppressed or prevented from generating interference fringes.
Further, an antireflection layer may be further formed so as to cover the hard coat layer 4.

As the antireflection layer, for _{example, SiO 2, SiO, ZrO 2} , TiO 2, TiO, Ti 2 O 3, Ti 2 O 5, Al 2 O 3, TaO 2, Ta 2 O 5, NbO, Nb 2 O ₃ , NbO ₂ , Nb ₂ O ₅ , CeO ₂ , MgO, Y ₂ O ₃ , SnO ₂ , MgF ₂ , and WO ₃ .
Such an antireflection layer can be formed by using, for example, a vacuum deposition method, an ion plating method, a sputtering method, or the like.

The average thickness of the antireflection layer is not particularly limited, but is preferably 50 to 150 nm, and more preferably 70 to 120 nm.
Furthermore, a water-repellent antifouling layer may be formed so as to cover the antireflection layer.
Such an antifouling layer can be obtained, for example, by forming a monomolecular film composed of an organosilicon compound containing fluorine on the antireflection layer.

As the organosilicon compound containing fluorine, general formula (2): R ² SiX ¹ ₃ (in general formula (2), R ² is an organic group having 1 or more carbon atoms containing fluorine, and X ¹ is hydrolyzed. Represents a decomposing group).
The antifouling layer is prepared, for example, by preparing an antifouling layer forming material in which a fluorine-containing organosilicon compound is dissolved in a solvent, and then applying the antifouling layer forming material onto the antireflection layer by using a coating method. After coating, it can be obtained by drying. Examples of the coating method include an ink jet method dipping method and a spin coating method.
The average thickness of the antifouling layer is not particularly limited, but is preferably 0.001 to 0.5 μm, and more preferably 0.001 to 0.03 μm.
The spectacle lens 1 as described above can be manufactured by the following spectacle lens manufacturing method by applying the optical member manufacturing method of the present invention.

  The method for producing an optical member of the present invention is a method for producing an optical member having a lens substrate having a curved concave surface and a hard coat layer formed so as to cover the curved concave surface. In a state where the concave surface is vertically upward, a supply process for supplying a hard coat layer forming material that forms a liquid for forming the hard coat layer to the curved concave surface using a coating method, and the lens substrate are turned upside down. A reversing step in which the curved concave surface is directed vertically downward, and a heating step of heating the hard coat layer forming material to form a hard coat layer.

Hereinafter, each process of manufacturing a spectacle lens by applying the method for manufacturing an optical member of the present invention will be described in detail.
FIG. 2 is a view (longitudinal sectional view) for explaining a first embodiment of a method for manufacturing a spectacle lens to which the method for manufacturing an optical member of the present invention is applied. Note that an arrow g in FIG. 2 indicates a vertical direction (direction in which gravity acts).

[A] First, the lens substrate 6 having the primer layer 3 formed on the curved concave surface (lower surface) 21 of the base material 2 is prepared.
The primer layer 3 is formed by, for example, preparing a primer layer forming material in which the constituent material of the primer layer 3 is dissolved in a solvent, and then applying the primer layer forming material onto the base material 2 using a coating method. Then, it can be performed by drying.
In addition, when the constituent material of the primer layer 3 does not melt | dissolve in a solvent, it can be set as the primer layer formation material which disperse | distributed the said constituent material.

  The solvent is not particularly limited. For example, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monopropyl ether acetate, ethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, Propylene glycol monopropyl ether acetate, propylene glycol monobutyl ether acetate, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dipropyl ether, ethylene glycol dibutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethyl Glycol dipropyl ether, diethylene glycol dibutyl ether, glycols such as propylene glycol dimethyl ether or propylene glycol diethyl ether and the like, can be used as these single solvent or a mixed solvent.

In addition, the primer layer forming material may include a polyoxyalkylene and polydimethylsiloxane copolymer or a polyoxyalkylene and fluorocarbon copolymer as a leveling agent.
Examples of the coating method used for forming the primer layer 3 include a dipping method, a spin coating method, and a spray method.
As described above, the lens substrate 6 having the curved concave surface 61 is prepared.

[B] Next, the hard coat layer 4 is formed so as to cover the curved concave surface 61 of the lens substrate 6 (primer layer 3).
[B-1] First, in a state where the curved concave surface 61 of the lens substrate 6 is vertically upward, a liquid hard coat layer forming material for forming a hard coat layer is applied to the curved concave surface 61 using a coating method. The liquid coating 41 is formed by supplying. (Supply process). “Vertical” means the direction in which gravity acts. That is, “vertically upward” means a relatively upper side in the direction in which gravity acts, and “vertically downward” means a relatively lower side in the direction in which gravity acts.

The hard coat layer forming material has the general formula (1): (R ¹ ) _n Si (X ¹ ) _4-n (in the general formula (1), R ¹ has 2 or more carbon atoms having a polymerizable functional group) An organic group, X ¹ represents a hydrolyzable group, and n represents an integer of 1 or 2. The organic silicon compound represented by (1) is dissolved in a solvent to form a liquid (sol). The method for producing an optical member of the present invention is more suitably applied when the hard coat layer forming material is a sol.
Examples of the organosilicon compound represented by the general formula (1) include those having an amino group as a polymerizable functional group, specifically, those represented by the following general formula (1A). .

(R ² ) _n Si (X ¹ ) _4-n (1A)
(In General Formula (1A), R ² represents a monovalent hydrocarbon group having 2 or more carbon atoms having an amino group, X ¹ represents a hydrolyzable group, and n represents an integer of 1 or 2.)

In the general formula (1A), R ² is a monovalent hydrocarbon group having 2 or more monovalent carbons having an amino group, such as γ-aminopropyl group, N-β (aminoethyl) -γ-aminopropyl group, N-phenyl-γ-aminopropyl group and the like can be mentioned.
Incidentally, in the general formula (1A), n represents an integer of 1 or 2, more R ² in the case (n = 2) in which R ² are a plurality may be the same or different from each other, a plurality of X ¹ may be the same as or different from each other.

Specific examples of the organosilicon compound represented by the general formula (1A) include, for example, γ-aminopropyltrimethoxysilane, γ-aminopropyldimethoxymethylsilane, γ-aminopropyltriethoxysilane, and γ-aminopropyldiethoxymethyl. Silane, N-β (aminoethyl) γ-aminopropyldimethoxymethylsilane, N-β (aminoethyl) γ-aminopropyltrimethoxysilane, N-β (aminoethyl) γ-aminopropyltriethoxysilane, N-β (Aminoethyl) γ-aminopropyldiethoxymethylsilane, N-phenyl-γ-aminopropyltrimethoxysilane, N-phenyl-γ-aminopropyldimethoxymethylsilane, N-phenyl-γ-aminopropyltriethoxysilane, N -Phenyl-γ-aminopropyldiethyl Amino-based silane coupling agent such as methylsilane and the like.
Furthermore, examples of the organosilicon compound represented by the general formula (1) include those having an isocyanate group as a polymerizable functional group, specifically, those represented by the following general formula (1B). Can be mentioned.

(R ³ ) _n Si (X ¹ ) _4-n (1B)
(In general formula (1B), R ³ represents a monovalent hydrocarbon group having 2 or more carbon atoms having an isocyanate group, X ¹ represents a hydrolyzable group, and n represents an integer of 1 or 2.)

In the general formula (1B), R ³ is a monovalent hydrocarbon group having 2 or more carbon atoms having an isocyanate group, such as an isocyanate methyl group, an α-isocyanatoethyl group, a β-isocyanatoethyl group, an α-isocyanatopropyl. Group, β-isocyanatopropyl group, γ-isocyanatopropyl group and the like.
In the general formula (1B), n represents an integer of 1 or 2, may be when there are a plurality of R ³ may have different plural R ³ is identical to each other, when plural X ¹ is The plurality of X ¹ may be the same as or different from each other.

Specific examples of the compound represented by the general formula (1B) include γ-isocyanatopropyltrimethoxysilane, γ-isocyanatopropyldimethoxymethylsilane, γ-isocyanatopropyltriethoxysilane, and γ-isocyanatopropyldiethoxymethyl. Examples thereof include isocyanate-based silane coupling agents such as silane.
Furthermore, examples of the organosilicon compound represented by the general formula (1) include those having an epoxy group as a polymerizable functional group, specifically, those represented by the following general formula (1C). Can be mentioned.

(R ⁴ ) _n Si (X ¹ ) _4-n (1C)
(In general formula (1C), R ⁴ represents a monovalent hydrocarbon group having 2 or more carbon atoms having an epoxy group, X ¹ represents a hydrolyzable group, and n represents an integer of 1 or 2.)

In the general formula (1C), R ⁴ is a monovalent hydrocarbon group having 2 or more carbon atoms having an epoxy group.
Incidentally, in the general formula (1C), n represents an integer of 1 or 2, it may be the case where R ⁴ have multiple or different plural R ⁴ are identical to one another, when plural X ¹ is The plurality of X ¹ may be the same as or different from each other.

  Specific examples of the compound represented by the general formula (1C) include, for example, glycidoxymethyltrimethoxysilane, glycidoxymethyltriethoxysilane, α-glycidoxyethyltrimethoxysilane, α-glycidoxyethyltri Ethoxysilane, β-glycidoxyethyltriethoxysilane, β-glycidoxypropyltrimethoxysilane, α-glycidoxypropyltrimethoxysilane, α-glycidoxypropyltriethoxysilane, β-glycidoxypropyltri Ethoxysilane, γ-glycidoxypropyltrimethoxysilane, (3,4-epoxycyclohexyl) methyltrimethoxysilane, γ-glycidoxypropylvinyldiethoxysilane, γ-glycidoxypropylphenyldiethoxysilane, δ- (3,4-epoxycyclohexyl ) Butyltriethoxysilane and the like.

In addition, the hard coat layer forming material can be used as a curing catalyst for accelerating hydrolysis and polycondensation reactions, and various solvents and interfaces for the purpose of improving wettability and improving smoothness when applied to a lens substrate. An activator or the like may be contained. Furthermore, ultraviolet absorbers, antioxidants, light stabilizers, and the like can be added to the hard coat layer forming material as long as they do not affect the physical properties of the hard coat layer.
Examples of the curing catalyst include inorganic acids such as hydrochloric acid, sulfuric acid, and nitric acid, and organic acids such as oxalic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, and lactic acid.

  Examples of the solvent used for the hard coat layer forming material, that is, the solvent for dissolving the organic silicon compound, include water, organic solvents, and mixed solvents thereof. Specifically, water such as pure water, ultrapure water, and ion exchange water, alcohols such as methanol, ethanol, isopropanol, n-butanol, and methyl isocarbinol, acetone, 2-butanone, ethyl amyl ketone, diacetone Ketones such as alcohol, isophorone, cyclohexanone, amides such as N, N-dimethylformamide, N, N-dimethylacetamide, diethyl ether, isopropyl ether, tetrahydrofuran, 1,4-dioxane, 3,4-dihydro-2H- Ethers such as pyran, glycol ethers such as 2-methoxyethanol, 2-ethoxyethanol, 2-butoxyethanol, ethylene glycol dimethyl ether, 2-methoxyethyl acetate, 2-ethoxyethyl acetate, 2-butoxy Glycol ether acetates such as tilacetate, methyl acetate, ethyl acetate, isobutyl acetate, amyl acetate, ethyl lactate, esters such as ethylene carbonate, aromatic hydrocarbons such as benzene, toluene, xylene, hexane, heptane, iso- Aliphatic hydrocarbons such as octane and cyclohexane, halogenated hydrocarbons such as methylene chloride, 1,2-dichloroethane, dichloropropane and chlorobenzene, sulfoxides such as dimethyl sulfoxide, N-methyl-2-pyrrolidone, N- Examples include pyrrolidones such as octyl-2-pyrrolidone.

  Further, the coating method for supplying the hard coat layer forming material to the curved concave surface 61 is not particularly limited. For example, the inkjet method, spin coating method, spray coating method, dip coating method, roll coating method, slit coater method, transfer Among them, the spray coating method is preferable (see FIG. 2A). The spray coating method is suitable for forming the hard coat layer 4 having a relatively thick film thickness as described above, and further, a curved concave surface in which a liquid hard coat layer forming material (sol) is directed vertically upward. 61 can be supplied uniformly.

[B-2] Next, as shown in FIG. 2B, the lens base 6 is turned upside down so that the curved concave surface 61 faces vertically downward (reversing step).
Here, after the supply of the hard coat layer forming material that forms a liquid to the curved concave surface 61 in the step [B-1], the curved concave surface 61 is maintained in a vertically upward state. Since the hard coat layer forming material flows down on the curved concave surface 61 and stays on the center side of the curved concave surface 61, when the hard coat layer is heated to form the hard coat layer in this state, the center of the curved concave surface 61 is formed. A thick film portion is formed in the portion.

  On the other hand, in the present invention, after the hard coat layer forming material is supplied, the lens base 6 is turned upside down so that the curved concave surface 61 faces vertically downward. Therefore, after the reversing step, the hard coat layer forming material flows down on the curved concave surface 61 that is vertically downward, and the hard coat layer forming material remains on the edge of the curved concave surface 61. Therefore, in this state, in the next step [B-3], the hard coat layer forming material is heated to form the hard coat layer 4, whereby the thick film portion 5 can be formed at the edge of the curved concave surface 61. .

  In this step, it is only necessary that the curved concave surface 61 be vertically downward. However, as shown in FIG. 2B, the height of the end surface 63 is the same at the edge in the left-right direction. Is preferred. That is, it is preferable that the tangent of the curved concave surface 61 is perpendicular to the vertical direction. Thereby, the thick film part 5 with a more uniform film thickness can be formed in a state of being unevenly distributed on the edge part of the curved concave surface 61.

[B-3] Next, as shown in FIG. 2C, the hard coat layer forming material is heated to form the hard coat layer 4 (heating step).
By heating the hard coat layer-forming material, hydrolyzable groups X ^1, wherein the organic silicon compound represented by the general formula (1) is possessed, gelled by siloxane oligomer is produced by hydrolysis and polycondensation reactions The hard coat layer 4 is formed by a so-called sol-gel method.

  When the hard coat layer 4 is formed by heating such a hard coat layer forming material, the curved concave surface 61 is directed vertically downward in the step [B-2]. Forming material remains. Therefore, in this step, by heating the liquid coating (hard coat layer forming material) 41, the hard coat layer 4 including the thick film portion 5 at the edge of the curved concave surface 61 is formed.

  In the manufacturing method of the optical member of the present invention, the hard coat layer 4 including the thick film portion 5 is formed at the edge of the curved concave surface 61 as described above. The hard coat layer 4 is formed with a sufficient thickness, and the thick film portion 5 is formed outside the use region of the spectacle lens. Therefore, it is possible to reliably prevent the occurrence of interference fringes in the eyeglass lens usage region.

As described above, according to the present invention, after the hard coat layer forming material is supplied to the curved concave surface 61, the lens substrate 6 is turned upside down so that the curved concave surface 61 faces vertically downward, and then the hard coat layer forming material is heated. Thus, the hard coat layer 4 having a uniform thickness can be formed in the use region of the eyeglass lens 1 by a relatively simple process of forming the hard coat layer 4.
Moreover, the method for heating the hard coat layer forming material is not particularly limited, but it is preferable to heat at the first heating temperature and then at the second heating temperature.

The first heating temperature is preferably set to about 90 to 110 ° C., more preferably about 100 ± 5 ° C.
The heating time at the first heating temperature is set to about 1 to 10 minutes, more preferably about 5 to 10 minutes.
The second heating temperature is preferably set to about 110 to 130 ° C, more preferably about 120 ± 5 ° C.

The heating time at the second heating temperature is set to about 1-2 hours, more preferably about 1.5 ± 0.2 hours.
Furthermore, the atmosphere during heating is not particularly limited, but is an oxygen-containing atmosphere or an inert gas atmosphere such as nitrogen gas.
By heating under the above conditions, the hydrolysis / polycondensation reaction can surely proceed, so that the hard coat layer 4 having excellent film strength can be formed.

Second Embodiment
Next, a second embodiment of the spectacle lens manufactured by applying the method for manufacturing an optical member of the present invention will be described.
FIGS. 3A and 3B show a second embodiment in which an optical member manufactured by the method for manufacturing an optical member of the present invention is applied to a spectacle lens ((a) a plan view, (b) A shown in FIG. 3 (a). FIG. 4 is a longitudinal sectional view for explaining a second embodiment of a method for manufacturing a spectacle lens to which the method for manufacturing an optical member of the present invention is applied. In the following, the upper side in FIGS. 3B and 4 is referred to as “upper”, and the lower side is referred to as “lower”. 3 and 4, for convenience of explanation, the size and thickness of members constituting the spectacle lens are schematically shown exaggerated, and the size and thickness of each member are actually Are very different.

Hereinafter, the spectacle lens 1 of the second embodiment will be described focusing on the differences from the spectacle lens 1 of the first embodiment, and the description of the same matters will be omitted.
In the eyeglass lens 1 shown in FIG. 3, a hard coat layer 4 ′ is further formed on the curved convex surface 62 of the lens substrate 6 that also has a primer layer 3 ′ formed so as to cover the curved convex surface 22 of the base material 2. The eyeglass lens 1 is the same as the eyeglass lens 1 shown in FIG.

That is, in the spectacle lens 1 of the second embodiment, the primer layer 3 and the primer layer 3 ′ are respectively formed on the curved concave surface 21 and the curved convex surface 22 of the base material 2, and further, the base material 2, the primer layer 3, and the primer A hard coat layer 4 and a hard coat layer 4 ′ are formed on the curved concave surface 61 and the curved convex surface 62 of the lens substrate 6 composed of the layer 3 ′, respectively.
And in both hard-coat layers 4 and 4 ', the thick film part 5 and 5' whose film thickness becomes thicker than a center part in the edge part is formed.

In the eyeglass lens 1 according to the second embodiment, the same effect as that of the first embodiment can be obtained. That is, it is possible to reliably prevent the occurrence of interference fringes in the eyeglass lens usage region.
In the eyeglass lens 1 of the second embodiment, in the step [A], the primer layers 3 and 3 ′ are formed on both the curved surfaces 21 and 22 of the base material 2 and the step [B -2], the lens base material 6 is turned upside down so that the curved concave surface 61 faces vertically downward, and then the hard coat layer forming material is supplied to the curved convex surface 62 using a coating method (convex surface supplying step). Can be manufactured.

That is, as shown in FIG. 4, prior to the step [B-3], the hard coat layer is formed on the curved convex surface 62 that is vertically upward of the lens substrate 6 having the base material 2 and the primer layers 3 and 3 ′. The spectacle lens 1 of the second embodiment can be manufactured by supplying the forming material using a coating method to form the liquid coating 41 ′.
As described above, when the hard coat layer forming material is supplied to the curved convex surface 62 with the curved concave surface 61 facing vertically downward, that is, the curved convex surface 62 facing vertically upward, the hard coat layer forming material flows down the curved convex surface 62 and curved. The hard coat layer forming material remains on the edge of the convex surface 62. Therefore, in this state, in [B-3], the hard coat layer forming material is heated to form the hard coat layer 4 ′, thereby forming the thick film portion 5 ′ at the edge of the curved convex surface 62. it can.

In addition, the dimension of each part is the same as that of the eyeglass lens 1 of the first embodiment.
The optical member is not limited to the eyeglass lens described in each of the embodiments, and can be applied to various lenses that transmit light. For example, the optical member can be applied to a lens included in a television, a projector, a computer display, or the like. it can.
As mentioned above, although the manufacturing method of the optical member of this invention was demonstrated, this invention is not limited to this.
For example, in the method for producing an optical member of the present invention, the order of the steps may be changed without being limited to the configuration of the embodiment. In addition, one or two or more arbitrary processes may be added, and unnecessary processes may be deleted.

1. Preparation of hard coat layer forming material In a stainless steel container, 46 parts by weight of 3-glycidoxypropyltrimethoxysilane (Momentive Performance Materials Japan GK, “TSL8350”), 42 parts by weight of 0.05N HCl Was added, and after sufficient stirring, 86 parts by weight of SiO ₂ sol (manufactured by JGC Catalysts & Chemicals, solid content 20%), silicone surfactant (“L7604” manufactured by Toray Dow Corning), 300 ppm, Fe catalyst 0.2 Part by weight and 0.8 part by weight of an Al-based catalyst were added and stirred sufficiently, and then MeOH was mixed and stirred so that the solid content was 25% to obtain a hard coat layer forming material.

2. Production of laminated body (glasses lens) (Example)
<1> First, as a lens base material, a plastic lens base material for eyeglasses with a refractive index of 1.67 (manufactured by Seiko Optical Products, “Seiko Super Sovereign (SSV)”) is prepared. A low-pressure mercury lamp (UV) was irradiated for 30 seconds on both the curved concave surface and the curved convex surface of the lens substrate.

<2> Next, in a state where the curved concave surface of the lens base material is set upward, an ultrasonic spray coat apparatus (“ExactaCoat” manufactured by Sono-tech Co., Ltd.) is used. The hard coat layer forming material adjusted in (1) was applied (supplied) from the upper side of the curved concave surface to form a coating film.
<3> Next, the lens base material is turned upside down, and the curved concave surface is repositioned downward, and thereafter, from the upper side of the curved convex surface turned upward, in the same manner as in the above step <2>. The hard coat layer forming material prepared in (1) was applied (supplied) to form a coating film.
<4> Next, the curved concave surface of the lens substrate and the curved concave surface of the lens substrate are dried by heating under the condition of 80 ° C. × 30 minutes with the curved concave surface facing downward (the curved convex surface facing upward). A lens with a hard coat of an example in which a hard coat layer was formed on both curved convex surfaces was obtained.

(Comparative example)
<1 ′> First, in the same manner as in the above step <1>, UV treatment was performed on both the curved concave surface and the curved convex surface of the lens substrate.
<2 ′> Next, in a state where the curved convex surface of the lens base material is set upward, an ultrasonic spray coat apparatus (“ExactaCoat” manufactured by Sono-tech Co., Ltd.) is used. The hard coat layer forming material adjusted in (1) was applied (supplied) from the upper side of the curved concave surface to form a coating film.

<3 ′> Next, the lens base material is turned upside down, and the curved convex surface is repositioned downward. Then, from the upper side of the curved concave surface that has turned upward, in the same manner as in the step <2 ′>, 1. The hard coat layer forming material prepared in (1) was applied (supplied) to form a coating film.
<4 '> Next, the curved concave surface of the lens base material is dried by heating the film with the curved convex surface facing downward (the curved concave surface facing upward) by heating at 80 ° C. for 30 minutes. The lens with the hard coat of the comparative example in which the hard coat layer was formed on both the curved convex surface was obtained.

3. Evaluation on the thickness of the hard coat layer About the lens with hard coat obtained in the examples and each comparative example, in the thickness direction, by using a microtome (Richert-Nissei ULTRACUT N), to create an observation cross section, The observation cross section was observed with a scanning electron microscope, and the film thickness of the hard coat layer formed on both the curved concave surface and the curved convex surface of the lens substrate was measured for the central portion and the edge portion, respectively.
In addition, the film thickness in the edge part of a hard-coat layer was taken as the film thickness in the position of 7 mm inside from the end surface of a lens.
The results are shown in Table 1.

As is apparent from Table 1, in the lens with a hard coat of the example, the hard coat layer is formed on both the curved convex surface side and the curved concave surface side from the center portion to the edge portion (position of 7 mm inside from the lens end surface). It was revealed that was formed with a uniform film thickness.
When the position closer to the end face than the position 7 mm on the inner side from the end face of the lens was observed, a thick film part having a thickness greater than that of the center part and the edge part was observed.

On the other hand, in the lens with the hard coat of the comparative example, the film thickness of the hard coat layer on both the curved convex surface side and the curved concave surface side is the center portion and the edge portion (at a position 7 mm inside from the end surface of the lens). It was uneven.
From the above, it was found that according to the method for manufacturing a lens with a hard coat of the example, a hard coat layer having a uniform film thickness can be formed in the use region of the lens without requiring time and labor.

  DESCRIPTION OF SYMBOLS 1 ... Glasses lens 2 ... Base material 21, 61 ... Curve concave surface 22, 62 ... Curve convex surface 3, 3 '... Primer layer 4, 4' ... Hard-coat layer 41, 41 '... Liquid film 5, 5' ... Thick film part 6 ... Lens substrate 63 ... End face

Claims (6)

A method of manufacturing an optical member,
With the curved concave surface of the lens base material vertically upward, supplying a hard coat layer forming material that forms a liquid for forming a hard coat layer so as to cover the curved concave surface;
Reversing the curved concave surface of the lens base material vertically downward;
And heating the hard coat layer forming material to form the hard coat layer.   After the reversing step, the hard coat layer forming material flows down the curved concave surface that is vertically downward and stays at the edge of the curved concave surface. The method for producing an optical member according to claim 1, wherein a thick film portion having a thick film thickness is formed at the portion.   The method of manufacturing an optical member according to claim 1, wherein the supplying is performed using a spray coating method. The hard coat layer forming material has the general formula (1): (R ¹ ) _n Si (X ¹ ) _4-n (in the general formula (1), R ¹ has 2 or more carbon atoms having a polymerizable functional group) An organic silicon compound represented by the formula: X ¹ represents a hydrolyzable group, and n represents an integer of 1 or 2. The organic silicon compound represented by the formula (1) is dissolved in a solvent. Manufacturing method of the optical member.   5. The method for producing an optical member according to claim 1, wherein the hard coat layer has an average thickness at a center portion of 5.0 μm or more and 50 μm or less. The lens substrate includes a curved convex surface facing the curved concave surface,
The optical member manufacturing method according to claim 1, further comprising supplying a hard coat layer forming material for forming the hard coat layer to the curved convex surface of the lens base prior to the heating step. Method.

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