JP5693210B2 - Method for producing plastic lens and plastic lens obtained from the method - Google Patents

Description

The present invention relates to a method for producing a plastic lens in which a hard coat layer film is formed on a plastic lens substrate, and at least an antireflection layer film is formed on the surface thereof. Furthermore, the present invention relates to a plastic lens formed by forming at least a hard coat layer film and an antireflection layer film on a plastic lens substrate.

  In recent years, as a material for optical lenses, particularly spectacle lenses, plastic substrates are mainly used instead of inorganic glass substrates. This is because the plastic substrate is superior in terms of lightness, impact resistance, processability, dyeability, etc., and the development and improvement of the plastic lens substrate as the second generation has been carried out. This is because the refractive index has been increased. However, these plastic substrates have the drawback of being easily damaged compared to inorganic glass substrates.

  In order to avoid this drawback, a silicone-based curable coating film (so-called hard coat layer film) is usually provided on the surface of an optical lens using a plastic substrate. Furthermore, when a plastic lens substrate having a high refractive index is used, in order to prevent light interference (this appears as interference fringes) between the lens substrate and the hard coat layer film, The layer film includes metal oxide fine particles, and a treatment is performed to match the refractive index with the refractive index of the lens. For example, Patent Document 1 discloses the use of composite oxide fine particles containing titanium oxide, zirconium oxide, antimony pentoxide and the like as the metal oxide fine particles.

  In addition, the present inventors have proposed in Patent Document 2 to use core-shell type metal oxide fine particles in which titanium oxide-based fine particles are used as core particles and the surface thereof is coated with antimony oxide. .

  Further, in an optical lens in which the hard coat layer film is provided on the surface of the plastic lens substrate and the antireflection layer film is further provided on the surface by a conventionally known vacuum vapor deposition method (so-called dry method), the temperature is relatively high. When this lens is left in an atmosphere, not only is it easy for cracks to occur in these coating films, but it also has the disadvantage of being easily cracked when an impact is applied to the lens.

  In order to solve this drawback, for example, in Patent Document 3, an antireflection layer film is formed by applying a coating composition containing an organosilicon compound and silica fine particles on the hard coat layer film, and further heat-curing the coating film. A method (so-called wet method) has been proposed. However, when an antireflection layer film is formed on the basis of this wet method, a long time is required for heat curing of the coating film, resulting in a problem that productivity and workability are lowered.

On the other hand, a method of applying a thermosetting coating composition or the like to the surface of a plastic substrate and irradiating a far infrared ray having a wavelength of 3 μm or more to the obtained coating film to cure the coating film is already common. Known to. For example, in Patent Document 4, a coating mainly composed of a partially hydrolyzed condensate of alkyltrialkoxysilane is applied to the surface of a plastic molded article, and further 0.1 to 100 cm away from the object to be coated. A surface curing method for a plastic molded article is disclosed in which a cured film is formed by radiating far infrared rays having a wavelength of 3 to 50 μm generated from a far infrared radiation element having a total radiation energy of 1.5 W / cm ² .

  However, such a conventionally known infrared curing method is used for curing a coating film (particularly, the antireflection layer film) formed on a plastic lens substrate such as a spectacle lens having a curved surface. When applied, there is a problem that unevenness of curing occurs on the surface or inside of the coating film. This is thought to be due to the fact that the difference in heat (irradiation intensity difference) occurs on the curved surface of the plastic lens substrate because the irradiation intensity received by the object is inversely proportional to the square of the distance from the far-infrared irradiation source. It is done.

JP-A-5-264806 JP 2009-197078 A JP 2006-146131 A Japanese Examined Patent Publication No. 63-17294

  The present invention has been made in view of the above-described problems in the prior art, and a laminated coating film composed of a hard coat layer film and an antireflection layer film on a plastic substrate can be cured in a relatively short time without unevenness. It is an object of the present invention to provide a plastic lens manufacturing method capable of manufacturing a plastic lens excellent in heat resistance and impact resistance.

  As a result of intensive studies aimed at solving the above-mentioned problems, the present inventors have obtained a coating composition for forming a specific hard coat layer film on a plastic lens substrate. The coated film is pre-cured under specific conditions, and a specific anti-reflective coating composition is applied to the surface of the coated film. As a result, the present invention was completed.

The method for producing a plastic lens according to the present invention includes:
In a method for producing a plastic lens, in which a hard coat layer film is formed on a plastic lens substrate, and an antireflection layer film is further formed on the surface thereof,
(1) A step of applying a hard coat layer film-forming coating composition containing an organosilicon compound (A), metal oxide fine particles and a polycarboxylic acid compound on a plastic lens substrate,
(2) A step of pre-curing the coating film by heat-treating the coating film obtained in the step (1) under a temperature condition of 60 to 110 ° C. for 5 to 30 minutes,
(3) A step of applying a coating composition for forming an antireflection layer film containing an organosilicon compound (B) and silica-based fine particles to the surface of the precured coating film obtained in the step (2), and (4 ) It is characterized by including the process of irradiating the laminated coating film obtained at the said process (3) with the far infrared rays which have a wavelength of 3-20 micrometers for 5 to 30 minutes, and hardening this laminated coating film.

The organosilicon compounds (A) and (B) are preferably an organosilicon compound represented by the following general formula (I) and / or a hydrolyzate thereof.
R ¹ _a R ² _b Si (OR ³ ) _{4- (a + b)} (I)
(In the formula, R ¹ is an alkyl group having 1 to 6 carbon atoms, an organic group having 8 or less carbon atoms containing a vinyl group, an organic group having 8 or less carbon atoms containing an epoxy group, and 8 carbon atoms containing a methacryloxy group. The following organic group, an organic group having 1 to 5 carbon atoms containing a mercapto group or an organic group having 1 to 5 carbon atoms containing an amino group, R ² is an alkyl group having 1 to 3 carbon atoms, an alkylene group, A cycloalkyl group, a halogenated alkyl group or an aryl group, R ³ is an alkyl group having 1 to ³ carbon atoms, an alkylene group or a cycloalkyl group, a is an integer of 0 or 1, b is 0, 1 Or an integer of 2.)

  The metal oxide fine particles are oxidized of at least one metal element selected from titanium, iron, zinc, tungsten, tin, tantalum, zirconium, antimony, niobium, indium, cerium, silicon, aluminum, yttrium, lead and molybdenum. Preferably, the fine particles are composite fine particles or complex oxide fine particles.

  Further, the metal oxide fine particles are at least one metal element selected from titanium, iron, zinc, tungsten, tin, tantalum, zirconium, antimony, niobium, indium, cerium, silicon, aluminum, yttrium, lead and molybdenum. A core-shell type in which the surface of a core particle composed of oxide fine particles or composite oxide fine particles is coated with an oxide or composite oxide of at least one metal element selected from silicon, zirconium, antimony, tin and aluminum The metal oxide fine particles are preferred.

The polycarboxylic acid compound is preferably a polycarboxylic acid or a polycarboxylic anhydride.
Further, in the polycarboxylic acid compound, the weight of the polycarboxylic acid compound is represented by X, and the amount of the organosilicon compound (A) contained in the hard coat layer film-forming coating composition is converted to SiO ₂ When the weight determined on the basis is represented by Y, it is contained in the coating composition for forming a hard coat layer film in such a ratio that the weight ratio (X / Y) is 5/100 to 45/100. It is preferable.

The silica-based fine particles are preferably hollow silica-based fine particles having an average particle diameter of 40 to 100 nm and having cavities inside.
It is preferable to include a step (3a) of pre-curing the coating film by further heat-treating the coating film obtained in the step (3) under a temperature condition of 60 to 110 ° C. for 3 to 30 minutes. .
Moreover, it is preferable to include a step (3b) of applying a water-repellent coating treatment coating composition further containing a fluorine compound or a hydrolyzate thereof to the surface of the precured coating film obtained in the step (3a). .

Furthermore, the fluorine compound is preferably a fluorosilane compound having a hydrolyzable group.
Moreover, it is preferable to perform the irradiation of the far infrared rays in the step (4) using a far infrared ceramic heater so that the surface temperature of the laminated coating film becomes 70 to 130 ° C.

Further, it is preferable to further provide a primer layer film between the plastic lens substrate and the hard coat layer film.
Furthermore, it is preferable that the primer layer film is obtained by applying a primer layer film-forming coating composition containing an organic resin compound and metal oxide fine particles onto the plastic lens substrate and curing it.

The first plastic lens according to the present invention is:
(1) A coating composition for forming a hard coat layer film containing an organosilicon compound (A), metal oxide fine particles and a polycarboxylic acid compound is applied onto a plastic lens substrate, and (2) the resulting coating film. Is heated for 5 to 30 minutes under a temperature condition of 60 to 110 ° C. to pre-cure the coating film. (3) On the surface of the obtained pre-cured coating film, an organosilicon compound (B ) And a coating composition for forming an antireflection layer film containing silica-based fine particles, and (4) the obtained laminated coating film is irradiated with far infrared rays having a wavelength of 3 to 20 μm for 5 to 30 minutes. The laminated coating film is cured to form a hard coat layer film and an antireflection layer film on the plastic lens substrate.

The second plastic lens according to the present invention is:
(1) A coating composition for forming a hard coat layer film containing an organosilicon compound (A), metal oxide fine particles and a polycarboxylic acid compound is applied onto a plastic lens substrate, and (2) the resulting coating After heat-treating the film under a temperature condition of 60 to 110 ° C. for 5 to 30 minutes to perform pre-curing of the coating film, (3) an organosilicon compound ( B) and a coating composition for forming an antireflection layer film containing silica fine particles, (3a) the obtained coating film was heat-treated at a temperature of 60 to 110 ° C. for 3 to 30 minutes, After preliminary curing of the coating film, (3b) a coating composition for water repellent coating treatment containing a fluorine compound or a hydrolyzate thereof is applied, and (4) 3-20 μm is applied to the obtained laminated coating film. Irradiation with far infrared rays having a wavelength of 5 to 30 minutes, By curing the layered coating film, the hard coat layer film on a plastic lens substrate, and characterized by being obtained by forming an antireflection layer film and the water-repellent coating layer film.

  The plastic lens preferably further comprises a primer layer film between the plastic lens substrate and the hard coat layer film.

  A method for producing a plastic lens according to the present invention, that is, a specific hard coat layer film-forming coating composition containing an organosilicon compound (A), fine metal oxide particles and a polycarboxylic acid compound is applied onto a plastic lens substrate. The coating film thus obtained is pre-cured by heat treatment under a temperature condition of 60 to 110 ° C. for 5 to 30 minutes, and further comprises a coating composition for forming an antireflection layer film containing an organosilicon compound (B) and silica-based fine particles In a method for producing a plastic lens, a laminated coating film obtained by applying a product on the pre-cured coating film is irradiated with far infrared rays having a specific wavelength of 3 to 20 μm for 5 to 30 minutes to cure the laminated coating film. According to the present invention, a laminated coating film composed of a hard coat layer film and an antireflection layer film can be formed on the plastic substrate in a relatively short time without unevenness of curing. And impact resistance superior plastic lens can be produced.

Furthermore, according to the production method of the present invention, a laminated coating film excellent in adhesion, scratch resistance, abrasion resistance, weather resistance, and fading resistance can be easily formed on a plastic lens substrate.
The hard coat layer film-forming coating composition containing a polycarboxylic acid compound can be formed in a relatively short time without uneven curing on a plastic lens substrate having a curved surface. Using the composition, it is obtained by applying the antireflection layer film-forming coating composition before the coating film obtained by applying the composition (that is, the coating film for hard coat layer film) is completely cured. Irradiation of the far-infrared rays to the multilayer coating film (that is, the coating film for the hard coat layer film and the coating film for the antireflection layer film) and the main curing of the coating film for the hard coat layer film and the coating for the antireflection layer film This is because the curing (main curing) with the film is efficiently performed.

  In addition, although the reason for such an effect is not necessarily verified at present, the polycarboxylic acid compound contained in the pre-cured coating film for hard coat layer film is irradiated Absorption of infrared vibrational energy causes thermal vibration, and as a result, the temperature of the laminated coating film (particularly, the coating film for the antireflection layer) formed on the curved surface of the plastic lens substrate is It can be considered to be almost uniform.

  As described above, the plastic lens according to the present invention has excellent heat resistance, impact resistance, adhesion, scratch resistance, abrasion resistance, weather resistance, fading resistance, etc. It can be suitably used as a plastic lens.

  In addition to the above characteristics, the plastic lens having the surface of the plastic lens subjected to a water-repellent coating treatment with a fluorine-based compound has excellent characteristics in water resistance and hot water resistance. Furthermore, the plastic lens in which a primer layer film is provided between the plastic lens base material and the hard coat layer film constituting the plastic lens is more excellent in impact resistance than the above. have.

Hereinafter, a method for producing a plastic lens according to the present invention and a plastic lens obtained from the method will be specifically described.
The pure water used in the method of the present invention refers to ion-exchanged water, and the ultrapure water is obtained by further removing impurities contained in pure water, and the impurity content is 0.01 μg / L or less. Means things.

[Plastic lens manufacturing method]
The method for producing a plastic lens according to the present invention is a method for producing a plastic lens in which a hard coat layer film is formed on a plastic lens substrate, and an antireflection layer film is further formed on the surface thereof.
(1) A step of applying a hard coat layer film-forming coating composition containing an organosilicon compound (A), metal oxide fine particles and a polycarboxylic acid compound on a plastic lens substrate,
(2) A step of pre-curing the coating film by heat-treating the coating film obtained in the step (1) under a temperature condition of 60 to 110 ° C. for 5 to 30 minutes,
(3) A step of applying a coating composition for forming an antireflection layer film containing an organosilicon compound (B) and silica-based fine particles to the surface of the precured coating film obtained in the step (2), and (4 ) A step of irradiating the laminated coating film obtained in the step (3) with far infrared rays having a wavelength of 3 to 20 μm for 5 to 30 minutes to cure the laminated coating film.
Next, each of these steps will be described as follows.

Process (1)
[Application of coating composition for forming hard coat layer film]
In this step, a hard coat layer film-forming coating composition containing an organosilicon compound (A), metal oxide fine particles and a polycarboxylic acid-based compound is applied onto a plastic lens substrate.

  The plastic lens substrate can be used without particular limitation as long as its refractive index is 1.49 to 1.80, preferably 1.60 to 1.74. These include various plastic lenses processed and manufactured using polystyrene resins, aliphatic allyl resins, aromatic allyl resins, polycarbonate resins, polythiourethane resins, polythioepoxy resins, etc. A substrate can be mentioned. In addition, any of these can be used as long as they are manufactured as plastic lens base materials (for example, including test supplies) regardless of whether they are currently on the market. is there.

As the coating composition for forming a hard coat layer film, a composition containing an organosilicon compound (A), metal oxide fine particles and a polycarboxylic acid compound is used.
Here, the organosilicon compound (A) is preferably an organosilicon compound represented by the following general formula (I) and / or a hydrolyzate thereof.

R ¹ _a R ² _b Si (OR ³ ) _{4- (a + b)} (I)
(In the formula, R ¹ is an alkyl group having 1 to 6 carbon atoms, an organic group having 8 or less carbon atoms containing a vinyl group, an organic group having 8 or less carbon atoms containing an epoxy group, and 8 carbon atoms containing a methacryloxy group. The following organic group, an organic group having 1 to 5 carbon atoms containing a mercapto group or an organic group having 1 to 5 carbon atoms containing an amino group, R ² is an alkyl group having 1 to 3 carbon atoms, an alkylene group, A cycloalkyl group, a halogenated alkyl group or an aryl group, R ³ is an alkyl group having 1 to ³ carbon atoms, an alkylene group or a cycloalkyl group, a is an integer of 0 or 1, b is 0, 1 Or an integer of 2.)

  Specific examples of the organosilicon compound (A) include tetraethoxysilane, methyltrimethoxysilane, vinyltrimethoxysilane, γ-methacryloxypropyltrimethoxysilane, trimethylchlorosilane, α-glucidoxymethyltrimethoxysilane. , Α-glycidoxyethyltrimethoxysilane, β-glycidoxyethyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, γ-glycidoxypropylmethyldimethoxysilane , Γ-glycidoxypropylmethyldiethoxysilane, β- (3,4-epoxycyclohexyl) -ethyltrimethoxysilane, β- (3,4-epoxycyclohexyl) -ethyltriethoxysilane, γ-aminopropyltrimethoxy Silane, γ-aminopropyltri Examples include ethoxysilane, N-β (aminoethyl) -γ-aminopropylmethyldimethoxysilane, N-β (aminoethyl) -γ-aminopropylmethyldiethoxysilane. Among these, in the method of the present invention, tetraethoxysilane, methyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropylmethyldiethoxysilane, β- (3,4-epoxycyclohexyl)- It is preferable to use ethyltrimethoxysilane or the like. These organosilicon compounds may be used in a mixture of not only one type but also two or more types.

Further, the organosilicon compound (A) is preferably contained in the hard coat layer film-forming coating composition in an amount of 10 to 35% by weight, preferably 15 to 30% by weight on the basis of SiO ₂ conversion. Here, when the content of the organosilicon compound (A) is less than 10% by weight in terms of SiO _{2, the} hard coat layer film-forming coating composition containing the organosilicon compound is used as a plastic lens substrate. When applied on top, the adhesion between the resulting coating film and the plastic lens substrate is undesirably reduced. In addition, when the content of the organosilicon compound (A) is more than 35% by weight on the basis of SiO ₂ conversion, the content of the metal oxide fine particles described below is relatively reduced. The coating film obtained by applying the coating composition for forming a hard coat layer film containing (hard coat layer film) may have poor scratch resistance or it may be difficult to form a coating film having a high refractive index. Therefore, it is not preferable.

  The metal oxide fine particles are manufactured for the purpose of coating on a plastic lens substrate regardless of whether they are currently commercially available, and have a refractive index of 1.52 to 2.70, preferably 1. If it is a thing of 60-2.60, it can be used without a restriction | limiting in particular.

  These metal oxide fine particles include at least one metal element selected from titanium, iron, zinc, tungsten, tin, tantalum, zirconium, antimony, niobium, indium, cerium, silicon, aluminum, yttrium, lead and molybdenum. And oxide fine particles and composite oxide fine particles.

  Further, oxide fine particles or composite oxidation of at least one metal element selected from titanium, iron, zinc, tungsten, tin, tantalum, zirconium, antimony, niobium, indium, cerium, silicon, aluminum, yttrium, lead and molybdenum Core / shell type metal oxide fine particles, etc., in which the surface of the core particles composed of fine particles is coated with an oxide or composite oxide of at least one metal element selected from silicon, zirconium, antimony, tin and aluminum Can be mentioned. Among these, when it is necessary to produce a plastic lens having a high refractive index and excellent in light resistance, weather resistance, etc., the core / core core coated with the composite oxide on the surface of titanium-containing core particles is used. It is preferable to use shell-type titanium metal oxide fine particles. Further, the core particles of the titanium-based metal oxide fine particles may have an anatase type crystal structure, or may have a rutile type crystal structure. Further, these metal oxide fine particles may be used in a mixture of not only one type but also two or more types.

  However, as the metal oxide fine particles, it is desirable to use those having an average particle size measured based on a dynamic light scattering method in the range of 7 to 60 nm, preferably 8 to 30 nm. Here, if the average particle diameter of the metal oxide fine particles is less than 7 nm, when the metal oxide fine particles are dispersed in an aqueous solution at a high concentration, the viscosity of the water-dispersed sol tends to remarkably increase. In addition, if the average particle diameter is more than 60 nm, light scattering on the particle surface increases, and as a result, the turbidity of the water-dispersed sol containing the metal oxide fine particles may increase. It is not preferable.

  In addition, the refractive index of the metal oxide fine particles varies depending on the type of metal element contained in the metal oxide fine particles and its configuration (for example, core-shell type particles), and the like, and is currently available on the market. The refractive index of the fine particles is generally in the range of 1.52 to 2.70. Therefore, it is preferable to use the plastic lens base material appropriately selected from those that match or substantially match the refractive index of the plastic lens substrate.

  The water-dispersed sol containing the metal oxide fine particles needs to be used in advance in a solvent replacement step or the like to prepare an organic solvent-dispersed sol when preparing the hard coat layer film-forming coating composition. There are many cases. In this case, the surface of the metal oxide fine particles is treated with a surface treatment agent such as an organosilicon compound such as a silane coupling agent or an amine compound in order to hydrophobize the surface of the metal oxide fine particles before being subjected to the solvent replacement step. It is common to keep it. Therefore, the metal oxide fine particles used in the present invention may be particles that have been subjected to a surface treatment using a surface treatment agent such as an organosilicon compound or an amine compound as described above.

In addition, the metal oxide fine particles (including those subjected to surface treatment) are included in the hard coat layer film forming coating composition in terms of MO _x (where M is a metal. The particles surface-treated with the silicon compound contain 10 to 70% by weight, preferably 15 to 60% by weight of the surface-treated substance in MO _x , that is, including the weight converted to SiO ₂ . It is preferable. Here, when the content of the metal oxide fine particles is less than 10% by weight in terms of MO _x , the metal oxide fine particles are relatively less than the content of the organosilicon compound (A). A coating film (hard coat layer film) obtained by applying the coating composition for forming a hard coat layer film containing fine particles becomes poor in scratch resistance or difficult to form a coating film having a high refractive index. This is not preferable. Further, when the content of the metal oxide fine particles is more than 70% by weight in terms of MO _{x, the} hard coat layer film-forming coating composition containing the metal oxide fine particles is formed on a plastic lens substrate. When applied, the adhesion between the resulting coating film and the plastic lens substrate may be reduced, or cracks may occur on the coating film surface when the coating film is cured, which is not preferable.

  The polycarboxylic acid compound is preferably a polycarboxylic acid or a polycarboxylic anhydride. Specific examples include polycarboxylic acids such as adipic acid, itaconic acid, malic acid, and benzenetetracarboxylic acid, and polycarboxylic acid anhydrides such as trimellitic anhydride, pyromellitic anhydride, and hexahydrophthalic anhydride. Of these, benzenetetracarboxylic acid, trimellitic anhydride, pyromellitic anhydride, itaconic acid and the like are preferably used from the viewpoint of excellent scratch resistance.

  Here, as described above, the polycarboxylic acid-based compound forms far infrared rays having a wavelength of 3 to 20 μm on the plastic lens substrate having a curved surface in the step (4) described later. When the laminated coating film (the coating film surface is also curved in the same manner as the plastic lens substrate) is irradiated, unevenness in curing occurs in the laminated coating film (particularly, the coating film for forming the antireflection layer). Since it has an effect of preventing the occurrence, it is an indispensable component in the coating composition for forming a hard coat layer film used in the present invention.

The polycarboxylic acid compound represents the weight of the polycarboxylic acid compound as X, and the amount of the organosilicon compound (A) contained in the hard coat layer film-forming coating composition is converted to SiO ₂ When the weight determined on the basis (hereinafter sometimes simply referred to as “SiO ₂ equivalent weight”) is represented by Y, the weight ratio (X / Y) is 5/100 to 45/100, preferably 10/100. It is preferably contained in the coating composition for forming a hard coat layer film at a ratio of ˜40 / 100. Here, if the weight ratio is less than 5/100, the time for pre-curing the coating film obtained by applying the hard coat layer film-forming coating composition may become longer, When the laminated coating obtained by applying a coating composition for forming an antireflection layer film on the coating is cured by irradiating far-infrared rays, the laminated coating (particularly for forming an antireflection layer film) is used. Unevenness of curing is likely to occur in the coating film), which is not preferable. Moreover, since the pot life of the said coating composition for hard-coat layer film formation will fall that the said weight ratio is larger than 45/100, it is unpreferable.

In addition, since the polycarboxylic acid-based compound also functions as a curing agent for a coating film obtained by applying the coating composition for forming a hard coat layer film, the hard coat layer is not necessarily an indispensable component. In the coating composition for film formation, it is further represented by the general formula M (CH ₃ COCHCOCH ₃ ) _n (where M is a metal element, n is an integer corresponding to the valence of M). Acetylacetone metal chelate compounds, metal alkoxides such as titanium alkoxide and zirconium alkoxide, alkali metal organic carboxylates such as sodium acetate and potassium acetate, perchloric acids such as lithium perchlorate and magnesium perchlorate, nitrogen such as imidazole and dicyandiamide It preferably contains a curing catalyst selected from the containing compounds. Among these, in the said coating composition for hard-coat layer film formation, it is preferable to use an acetylacetone metal chelate compound.

Here, the curing catalyst varies depending on the type and content of the organosilicon compound contained in the hard coat layer film-forming coating composition, and also the type and content of the polycarboxylic acid compound. Represents the weight ratio (V / Y) when the weight of the curing catalyst (MO _x equivalent weight) is represented by V and the content of the organosilicon compound (A) (SiO ₂ equivalent weight) is represented by Y. Is preferably added to the coating composition for forming a hard coat layer film at a ratio of 1/100 to 20/100, preferably 2/100 to 15/100.

  Further, in the coating composition for forming a hard coat layer film, a surfactant as a leveling agent or bluing that occurs when a plastic lens is used in an environment where ultraviolet rays fall as necessary is avoided. And a polyfunctional epoxy compound described in Japanese Patent No. 3203142 may be included.

  Here, examples of the surfactant include silicone surfactants such as polyoxyalkylene dimethylpolysiloxane, and fluorine surfactants such as perfluoroalkylcarboxylates and perfluoroalkylethylene oxide adducts. Can do. Among these, in the coating composition for forming a hard coat layer film used in the present invention, it is preferable to use a silicone-based surfactant from the viewpoint of reducing environmental load.

Moreover, as said ultraviolet absorber, a benzophenone type ultraviolet absorber, a benzotriazole type ultraviolet absorber, etc. can be used.
Furthermore, it is desirable that the coating composition for forming a hard coat layer film contains an organic solvent for dispersing the above components. Specifically, alcohols such as methanol, ethanol and propanol, ketones such as methyl ethyl ketone and acetyl acetone, esters such as ethyl acetate and butyl acetate, cellosolves such as ethyl cellosolve and butyl cellosolve, ethers such as propylene glycol monomethyl ether Etc. Among these, it is preferable that an organic solvent selected from methanol, propanol, propylene glycol monomethyl ether, and the like is included from the viewpoint of leveling property and evaporation rate.
However, the organic solvent is an organic solvent mixed with the organosilicon compound (A) at the time of preparing the hard coat layer film-forming coating composition and the organic solvent used at the time of preparing the organic solvent-dispersed sol of the metal oxide fine particles. It is desirable to use the solvent as it is. The organic solvents may be of different types as long as they are compatible, but it is preferable to use the same solvents as much as possible.

Furthermore, the organic solvent may be contained in such a ratio that the solid content in the coating composition for forming a hard coat layer film is 15 to 55% by weight, preferably 20 to 50% by weight. preferable. Here, the solid content refers to, among the components of the content of the organic silicon compound (A) (SiO ₂ in terms of weight), including particles subjected to the metal oxide fine particles (surface treatment .)) (In terms of MO _x equivalent weight), and further, the hard weight is the sum of the contents (in terms of MO _x equivalent weight) of the curing catalyst (if it is a metal-containing catalyst) added as necessary. It means a value obtained by dividing the total weight of the coating composition for forming a layer film by 100.
Here, if the solid content contained in the coating composition for forming a hard coat layer film is less than 15% by weight, a coating film having a sufficient film thickness cannot be obtained. If the solid content is more than 55% by weight, the pot life is likely to be lowered, which is not preferable.

  Next, a method for preparing the coating composition for forming a hard coat layer film will be specifically described. However, since the preparation method described here shows one aspect thereof, the coating composition for forming a hard coat layer film used in the present invention is not limited to those obtained from these preparation methods.

  (A) When the metal oxide fine particles are present in the form of a water-dispersed sol, the water-dispersed sol is subjected to an ultrafiltration device or the like, and water contained in the water-dispersed sol is methanol, propanol, propylene It is desirable to prepare an organic solvent-dispersed sol containing the metal oxide fine particles by replacing the solvent with an organic solvent such as glycol monomethyl ether. In this case, the metal oxide fine particles are preferably contained in the organic solvent-dispersed sol in an amount of 10 to 40% by weight.

  (B) Next, the organic solvent dispersion sol containing the metal oxide fine particles and the organosilicon compound (A) are mixed. As mentioned above, the organosilicon compound (A) used here is preferably an organosilicon compound represented by the following general formula (I) and / or a hydrolyzate thereof.

R ¹ _a R ² _b Si (OR ³ ) _{4- (a + b)} (I)
(In the formula, R ¹ is an alkyl group having 1 to 6 carbon atoms, an organic group having 8 or less carbon atoms containing a vinyl group, an organic group having 8 or less carbon atoms containing an epoxy group, and 8 carbon atoms containing a methacryloxy group. The following organic group, an organic group having 1 to 5 carbon atoms containing a mercapto group or an organic group having 1 to 5 carbon atoms containing an amino group, R ² is an alkyl group having 1 to 3 carbon atoms, an alkylene group, A cycloalkyl group, a halogenated alkyl group or an aryl group, R ³ is an alkyl group having 1 to ³ carbon atoms, an alkylene group or a cycloalkyl group, a is an integer of 0 or 1, b is 0, 1 Or an integer of 2.)
In addition, specific examples of the organosilicon compound (A) are as described above.

  (C) Here, the organosilicon compound (A) is previously mixed with an organic solvent such as methanol, propanol, propylene glycol monomethyl ether, and an acid and water as a hydrolysis catalyst are added to the mixture. After the hydrolysis of the organosilicon compound (A), it is preferable to mix with the organic solvent dispersion sol of the metal oxide fine particles (hereinafter sometimes simply referred to as “organic solvent dispersion sol”). However, the organic silicon compound (A) is mixed with the organic solvent-dispersed sol and then added with an acid and water as a hydrolysis catalyst (if water remains in the organic solvent-dispersed sol, It is not always necessary to add water.) And may be hydrolyzed.

  In addition, it is preferable to perform hydrolysis of the said organosilicon compound (A) over 1 to 48 hours on 5-30 degreeC temperature conditions, stirring. Moreover, after performing the said hydrolysis, stirring may be stopped and this liquid mixture may be aged on the temperature conditions of -20-0 degreeC over 1 to 7 days.

Thus, the precursor of the coating composition for forming a hard coat layer film is prepared by mixing the organosilicon compound (A) and the organic solvent-dispersed sol. The amount of (A) (weight converted to SiO ₂ ) is represented by Y, and the amount of metal oxide fine particles (including surface-treated particles) contained in the organic solvent-dispersed sol (MO _x converted weight) It is preferable that the weight ratio (Y / W) is 30/70 to 90/10, preferably 35/65 to 80/20. Here, if the weight ratio is less than 30/70, as described above, the adhesion to the substrate or other coating film may be lowered, and the weight ratio is 90/70. If it is more than 10, it is not preferred because the refractive index of the coating film and the scratch resistance on the coating film surface may be lowered.

  (D) Next, the polycarboxylic acid compound is mixed in the obtained mixed liquid and sufficiently stirred. Furthermore, stirring may be stopped and the mixed solution may be aged for 1 to 7 days under a temperature condition of -20 to 0 ° C.

  Moreover, you may add the said surfactant, the said ultraviolet absorber, etc. in the said liquid mixture, stirring, when mixing the said polycarboxylic acid type compound as needed. In this case, the polycarboxylic acid compound, the surfactant, the ultraviolet absorber, and the like may vary depending on their physical properties, but may be mixed in the mixed solution as they are, or dissolved in the organic solvent. Or you may mix after dispersing.

Thereby, the coating composition for hard-coat layer film formation used by this invention is prepared.
The hard coat layer film-forming coating composition thus obtained is obtained by using a conventionally known coating method selected from a dipping method, a spin coating method, a spray coating method, an inkjet coating method, etc. It can be applied onto a substrate.

Process (2)
[Pre-hardening of hard coat layer film]
In this step, the coating film formed on the plastic lens substrate in the step (1) is subjected to a heat treatment for 5 to 30 minutes at a temperature of 60 to 110 ° C., and the coating film is pre-cured. .

  Here, the preliminary curing of the coating film means a state where the coating film is not completely cured, and more specifically, the coating film is dry to the touch (can be confirmed to be dry by touching with a finger). Means the state.

  Moreover, as a method of performing this preliminary curing, although not particularly limited thereto, (1) the coating film formed on the plastic lens substrate is exposed to a hot air atmosphere or a circulating hot air atmosphere, Alternatively (2) there is a method of irradiating the coating film with far infrared rays.

  The heat treatment for pre-curing the coating film is desirably performed for 5 to 30 minutes under the condition that the surface temperature of the coating film is 60 to 110 ° C. Here, the heat treatment based on the method of (1) is performed by exposing the coating film in a hot air atmosphere or a circulating hot air atmosphere having thermal energy capable of imparting the surface temperature for 5 to 30 minutes, Moreover, it is preferable to perform the heat processing based on the method of said (2) by irradiating the far infrared rays of the wavelength range 3-20 micrometers which have the thermal energy which can provide the said surface temperature for 5 to 30 minutes. Further, in this case, according to the latter method, since the above-mentioned polycarboxylic acid compound functioning as a curing agent is contained in the coating film, it is heated from the inside of the coating film, so there is no uneven curing. Pre-curing of the coating film can be completed in a relatively short time. Further, in some cases, the methods (1) and (2) may be used in combination, but in this step, it is important to keep the coating film in a pre-cured state.

  Here, when the heat treatment temperature is lower than 60 ° C., the coating film is insufficiently cured, and when the coating composition for forming an antireflection layer film is applied in the next step, both coating film components are mixed. If the heat treatment temperature is higher than 110 ° C., the plastic lens is likely to be thermally deformed, which is not preferable. Furthermore, if the heat treatment time is less than 5 minutes, the coating film is insufficiently cured. If the heat treatment time is more than 30 minutes, the coating film is cured too much, This is not preferable because adhesion to the antireflection layer film formed in the process is insufficient.

  Further, the thickness of the coating film thus obtained (that is, the hard coat layer film) varies depending on the solid content contained in the coating composition for forming a hard coat layer film, but is 1.0. It is desirable to be in the range of ˜5.0 μm, preferably 1.5 to 3.5 μm. Furthermore, the refractive index of the coating film (hard coat layer film) varies depending on the type and content of the metal oxide fine particles contained in the coating composition for forming the hard coat layer film. The refractive index when fully cured is 1.52 to 1.80, preferably 1.55 to 1.78. However, for the refractive index of this coating film (hard coat layer film), if the refractive index does not match the refractive index of the plastic lens substrate used, interference vortices will appear on the surface of the resulting plastic lens, It is necessary to select the type of the metal oxide fine particles so that the refractive index of the plastic lens substrate matches or almost matches, and to appropriately adjust the content thereof.

Step (3)
[Application of coating composition for forming antireflection layer film]
In this step, a coating composition for forming an antireflection layer film containing an organosilicon compound (B) and silica-based fine particles is applied to the surface of the precured coating film obtained in the step (2).

As the coating composition for forming the antireflection layer film, a coating composition containing an organosilicon compound (B) and silica-based fine particles, preferably hollow silica-based fine particles is used.
Here, as the organosilicon compound (B), those similar to the organosilicon compound (A) can be used. That is, the organosilicon compound (B) is preferably an organosilicon compound represented by the following general formula (I) and / or a hydrolyzate thereof as in the case of the organosilicon compound (A).

R ¹ _a R ² _b Si (OR ³ ) _{4- (a + b)} (I)
(In the formula, R ¹ is an alkyl group having 1 to 6 carbon atoms, an organic group having 8 or less carbon atoms containing a vinyl group, an organic group having 8 or less carbon atoms containing an epoxy group, and 8 carbon atoms containing a methacryloxy group. The following organic group, an organic group having 1 to 5 carbon atoms containing a mercapto group or an organic group having 1 to 5 carbon atoms containing an amino group, R ² is an alkyl group having 1 to 3 carbon atoms, an alkylene group, A cycloalkyl group, a halogenated alkyl group or an aryl group, R ³ is an alkyl group having 1 to ³ carbon atoms, an alkylene group or a cycloalkyl group, a is an integer of 0 or 1, b is 0, 1 Or an integer of 2.)

  Specific examples of the organosilicon compound (B) include those described as specific examples of the organosilicon compound (A). Among these, tetraethoxysilane, methyltrimethoxysilane, γ-glycol are exemplified. Sidoxypropyltrimethoxysilane, β- (3,4-epoxycyclohexyl) -ethyltrimethoxysilane and the like are preferably used. In this case, the organosilicon compound (B) may be used by mixing not only one type but also two or more types.

Further, the organosilicon compound (B) is 0.5 to 5.5% by weight, preferably 1.0 to 4.5% by weight in terms of SiO _{2 in the} antireflection layer film forming coating composition. It is preferably included. Here, when the content of the organosilicon compound (B) is less than 0.5% by weight in terms of SiO _{2, the} antireflection layer film-forming coating composition containing the organosilicon compound is prepared as the preliminary composition. When applied on a cured coating film, the adhesion between the resulting coating film and the precured coating film (that is, the adhesion between the laminated coating films) decreases, and the scratch resistance becomes insufficient. Therefore, it is not preferable. Further, if the content of the organosilicon compound (B) is more than 5.5% by weight in terms of SiO ₂ , the content of the hollow silica-based fine particles described below is relatively reduced. Since the anti-reflective performance of the coating film (namely, anti-reflective layer film) obtained by apply | coating the said coating composition for anti-reflective layer film formation containing a silicon compound deteriorates, it is unpreferable.

  As the silica-based fine particles, those having an average particle diameter of 5 to 100 nm, preferably 40 to 100 nm can be used without particular limitation. However, the refractive index of the silica-based fine particles is different in the value between the non-porous silica-based fine particles and the porous silica-based fine particles, but is generally in the range of 1.35 to 1.46. When the coating film (hard coat layer film) obtained by applying the coating liquid for film formation contains metal oxide fine particles having a high refractive index, the antireflection layer film containing the silica-based fine particles on the coating film In the antireflection performance of the coating film (antireflection layer film) obtained by applying the forming coating solution, a desired one may not be obtained.

Therefore, as the silica-based fine particles, it is preferable to use hollow silica-based fine particles having an average particle diameter in the range of 40 to 100 nm, preferably 50 to 90 nm, and having cavities inside. Here, if the average particle diameter is less than 40 nm, it may be difficult to obtain an antireflection layer film having a uniform thickness depending on the coating method or processing method employed, and the average particle diameter is more than 100 nm. In this case, the design of the antireflection layer film becomes difficult.

  In the present invention, “hollow silica-based fine particles having a cavity inside” refers to hollow silica-based fine particles having a cavity inside an outer shell (shell part) made of a silica-based inorganic oxide, and “cavity”. The term “spheroidal space formed inside the particle” or “deformed space” contains a gaseous substance such as air.

  The refractive index of the hollow silica-based fine particles having such a structure varies depending on the porosity (ratio occupied by cavities in the particles), but is generally in the range of 1.15 to 1.35. When oxide particles having a high refractive index are used, it is preferable to use hollow silica particles having a low refractive index.

  The outer shell (shell part) made of the silica-based inorganic oxide is a silica-based composite oxide composed of silicon and a metal element other than silicon, such as —O—Si—O—Al—O—Si—O—. Or a composite oxide such as Here, examples of the metal element other than silicon include aluminum, boron, titanium, zirconium, tin, cerium, phosphorus, antimony, molybdenum, zinc, tungsten, and the like. Since it is intended to form an antireflective layer film having a low refractive index, it is preferably selected from those that do not increase the refractive index of the hollow silica-based fine particles or give photocatalytic activity.

  Further, the hollow silica-based fine particles may be those in which a coating layer made of a silica component is provided on the surface thereof using an organosilicon compound having a hydrolyzing group or a silicic acid solution. Here, the organosilicon compound is not particularly limited, and examples thereof include alkoxysilanes such as tetramethoxysilane, tetraethoxysilane, and tetraisopropoxysilane.

  Such hollow silica-based fine particles may be produced by a conventionally known production method such as JP 2001-233611, JP 2004-203683, JP 2006-21938, and International Publication WO 2006/009132. Can be produced based on the method described in 1. above. Further, the hollow organic / inorganic hybrid fine particles described in JP-A-2009-242475 are produced, and the surface thereof is obtained by a surface treatment (silica-based component coating) with a silane coupling agent or the like. Also good.

In the coating solution for forming the antireflection layer film, as in the case of the coating composition for forming the hard coat layer film, the general formula M (CH ₂ COCH ₂ COCH ₃ ) _n (where M represents a metal) ) Acetylacetone metal chelate compounds, titanium alkoxides, zircoalkoxides and other metal alkoxides, alkali metal organic carboxylates such as sodium acetate and potassium acetate, perchloric acids such as lithium perchlorate and magnesium perchlorate, imidazole It preferably contains a curing catalyst selected from nitrogen-containing compounds such as dicyandiamide. Among these, it is preferable to use an acetylacetone metal chelate compound or the like in the antireflection film layer-forming coating composition.

Here, the curing catalyst, the varies depending on the type and content of the organic silicon compound contained in the antireflection layer film forming coating composition, the weight of the cured catalyze (MO _x in terms of weight) V When the content of the organosilicon compound (A) (weight converted to SiO ₂ ) is represented by Y, the weight ratio (V / Y) is 1/100 to 20/100, preferably 2/100 to It is preferable to add to the coating composition for forming an antireflection layer film at a ratio of 15/100.

  Further, in the coating composition for forming the antireflection film layer film, the polycarboxylic acid compound used at the time of preparing the coating composition for forming the hard coat layer film, that is, polycarboxylic acid, polycarboxylic acid anhydride, etc. May be included. As described above, this polycarboxylic acid compound not only functions as a curing catalyst, but also functions to avoid uneven curing of the laminated coating film (particularly, the antireflection layer film) that occurs during irradiation with far infrared rays. have. However, the latter function, i.e., the function of avoiding unevenness of curing, is exerted to the maximum when the polycarboxylic acid-based compound is contained in the pre-cured coating film (hard coating layer coating film). Therefore, the polycarboxylic acid-based compound is not necessarily contained in the coating composition for forming the antireflection film layer.

Furthermore, the antireflection layer film forming coating composition may contain a surfactant as a leveling agent, the ultraviolet absorber, or the like, if necessary.
Here, examples of the surfactant include silicone surfactants such as polyoxyalkylene dimethylpolysiloxane, and fluorine surfactants such as perfluoroalkylcarboxylates and perfluoroalkylethylene oxide adducts. Can do. Among these, in the coating composition for forming an antireflection layer film used in the present invention, it is preferable to use a silicone-based surfactant from the viewpoint of reducing environmental load.
Examples of the ultraviolet absorber include benzophenone ultraviolet absorbers, benzotriazole ultraviolet absorbers, and hindered amine light stabilizers.

  Furthermore, it is desirable that the coating composition for forming an antireflection layer film contains an organic solvent for dispersing the above components. Specifically, alcohols such as methanol, ethanol and propanol, ketones such as methyl ethyl ketone and acetylacetone, esters such as ethyl acetate and butyl acetate, cellosolves such as ethyl cellosolve and butyl cellosolve, ethers such as propylene glycol monomethyl ether Etc. Among these, it is preferable that an organic solvent selected from methanol, propanol, propylene glycol monomethyl ether, and the like is included from the viewpoint of leveling properties and drying speed.

  However, the organic solvent is the organic solvent mixed with the organosilicon compound (B) when preparing the coating composition for forming the antireflection layer film and the organic solvent used when preparing the organic solvent-dispersed sol of the hollow silica fine particles. It is desirable to use the solvent as it is. The organic solvents may be of different types as long as they are compatible, but it is preferable to use the same solvents as much as possible.

Further, the organic solvent has a solid content of 1.0 to 8.0% by weight, preferably 2.0 to 6.0% by weight, in the coating composition for forming an antireflection layer film. It is preferable to be included in such a ratio. Note that the solids content referred to here, among the components described above, wherein said organic silicon compound content of (B) (SiO ₂ in terms of weight), the content of the silica fine particles (MO _x in terms of weight), Further, the total weight of the curing catalyst (however, in the case of a metal-containing catalyst) added as necessary (MO _x equivalent weight) is divided by the total weight of the coating composition for forming the antireflection layer film. It means a value multiplied by 100.

  Here, when the solid content contained in the coating composition for forming an antireflection layer film is less than 1.0% by weight, it becomes difficult to obtain a coating film having a sufficient film thickness, If the solid content is more than 8.0% by weight, it is not preferable because control for forming a desired thin film becomes difficult.

  Next, a method for preparing the coating composition for forming the antireflection layer film will be specifically described. However, since the preparation method described here shows one embodiment, the coating composition for forming an antireflection layer film used in the present invention is not limited to those obtained from these preparation methods.

Hereinafter, a preparation method when “hollow silica-based fine particles” are used as the silica-based fine particles will be described.
(A) When the hollow silica-based fine particles are present in a water-dispersed sol state, the water-dispersed sol is subjected to an ultrafiltration device or the like, and the water contained in the water-dispersed sol is methanol, propanol, propylene It is desirable to prepare an organic solvent-dispersed sol containing the hollow silica-based fine particles by replacing the solvent with an organic solvent such as glycol monomethyl ether. In this case, the hollow silica-based fine particles are preferably contained in the organic solvent-dispersed sol in an amount of 5 to 30% by weight.

  (B) Next, the organosilicon compound (B) and the organic solvent are mixed and sufficiently stirred. Examples of the organic solvent used here include alcohols such as methanol, ethanol, and propanol, and ethers such as propylene glycol monomethyl ether. Among these, compatibility with the organosilicon compound (B) is good. From this point of view, it is preferable to use methanol, ethanol, propanol or the like.

Further, as described above, the organosilicon compound (B) is preferably an organosilicon compound represented by the following general formula (I) and / or a hydrolyzate thereof.
R ¹ _a R ² _b Si (OR ³ ) _{4- (a + b)} (I)
(In the formula, R ¹ is an alkyl group having 1 to 6 carbon atoms, an organic group having 8 or less carbon atoms containing a vinyl group, an organic group having 8 or less carbon atoms containing an epoxy group, and 8 carbon atoms containing a methacryloxy group. The following organic group, an organic group having 1 to 5 carbon atoms containing a mercapto group or an organic group having 1 to 5 carbon atoms containing an amino group, R ² is an alkyl group having 1 to 3 carbon atoms, an alkylene group, A cycloalkyl group, a halogenated alkyl group or an aryl group, R ³ is an alkyl group having 1 to ³ carbon atoms, an alkylene group or a cycloalkyl group, a is an integer of 0 or 1, and b is 0 1 or an integer of 2)

In this case, the organosilicon compound (B) and the organic solvent are mixed in such a manner that the organosilicon compound (B) is 30 to 95% by weight, preferably 50 to 80% by weight in terms of SiO _{2 in the} mixed solution. It is preferable to carry out such that it is included.

In addition, specific examples of the organosilicon compound (B) are as described above.
(C) Next, an acid and water as a hydrolysis catalyst are added to the mixed solution to hydrolyze the organosilicon compound (B) contained in the mixed solution. However, when the organosilicon compound (B) has already been hydrolyzed, this operation is not necessarily performed.

  Here, the hydrolysis of the organosilicon compound (B) is preferably performed over a period of 1 to 48 hours under a temperature condition of 5 to 30 ° C. while stirring the mixed solution. Moreover, after performing the said hydrolysis, stirring may be stopped and this liquid mixture may be aged on the temperature conditions of -20-0 degreeC over 1 to 7 days.

  (D) Next, the organic solvent-dispersed sol of the hollow silica-based fine particles is mixed in the liquid mixture obtained above and sufficiently stirred. Furthermore, after that, stirring may be stopped and the mixed solution may be aged for 1 to 7 days under a temperature condition of -20 to 0 ° C.

In this case, in the mixing of the organic solvent dispersion sol, the amount of hollow silica-based fine particles (weight in terms of MO _x ) contained in the organic solvent dispersion sol is represented by K, and the organosilicon compound ( When the amount of B) (weight in terms of SiO ₂ ) is represented by Y, the weight ratio (K / Y) is 10/90 to 70/30, preferably 20/80 to 60/40. It is preferable. Here, if the weight ratio is less than 10/90, the refractive index of the coating film does not decrease, so that a sufficient antireflection function cannot be obtained, and the weight ratio is more than 70/30. And the scratch resistance is not preferred.

Thereby, the coating composition for antireflection layer film formation used by this invention is prepared.
The antireflection layer film-forming coating composition thus obtained is prepared by using the previously known coating method selected from a dipping method, a spin coating method, a spray coating method, an inkjet coating method, and the like. It can apply | coat on a coating film.

Step (4)
[Curing of multilayer coating film by far infrared rays]
In this step, the laminated coating film obtained in the step (3) is irradiated with far infrared rays having a wavelength of 3 to 20 μm for 5 to 30 minutes to cure the laminated coating film.

  The curing of the laminated coating film performed here is the main curing of the coating film (hard coat layer film) preliminarily cured in the step (2) and the coating film (antireflection layer film) applied in the step (3). The main curing is efficiently performed at the same time.

  The far-infrared irradiation is performed by horizontally placing a plastic lens base material provided with the laminated coating film with a lens holder, and laminating the plastic lens base material from a far-infrared heater placed directly above and below the plastic lens base material. It is preferable to carry out at right angles to the coating surface. Here, it is preferable that the far-infrared heater has a structure that can adjust the wavelength range of far-infrared rays emitted from the far-infrared heater and that can move in the vertical direction.

  The distance between the far-infrared heater and the laminated coating surface on the plastic lens substrate is 5 to 40 cm, preferably 10 to 20 cm. However, the adjustment of this distance is preferably performed while appropriately selecting in consideration of the amount of energy radiated from the far infrared heater, the surface temperature of the laminated coating film, and the like.

  As the far-infrared heater, a commercially available far-infrared ceramic heater capable of emitting far-infrared rays having a wavelength of 3 to 20 μm can be used. In addition, in the far-infrared ceramic heater (SI type) manufactured by Sakaguchi Electric Heat Co., Ltd. used in the present invention, the relationship between the radiant heating temperature and the peak wavelength is approximately 200 ° C. on the catalog. It is described as 6.15 μm with respect to 500 ° C. and 3.75 μm with respect to 500 ° C.

  Further, as described above, far-infrared rays having a wavelength of 3 to 20 μm, preferably 3.5 to 15 μm are used for curing the laminated coating film. Here, if the far-infrared wavelength is less than 3 μm, the amount of vibration energy absorbed in the laminated coating film is reduced, and if the far-infrared wavelength is more than 20 μm, Since the amount of vibration energy radiated from is reduced, both of the laminated coating films are not sufficiently cured. Furthermore, it is desired that the irradiation time of the far infrared ray is appropriately selected from the range of 5 to 30 minutes, preferably 7 to 20 minutes. Here, if the irradiation time is less than 5 minutes, curing of the laminated coating film may be insufficient, and if the irradiation time is more than 30 minutes, The purpose, that is, the purpose of efficiently completing the curing of the laminated coating film in as short a time as possible cannot be achieved, which is not preferable.

  Regarding infrared rays, 0.75 to 2.5 μm may be referred to as near infrared rays, 2.5 to 4 μm as medium infrared rays, 4 to 25 μm as far infrared rays, and 25 to 1000 μm as super far infrared rays depending on the wavelength range. However, in the present invention, the wavelength region of 3 to 20 μm is referred to as “far infrared rays”.

  Thus, it is desirable that the surface temperature of the laminated coating film irradiated with far-infrared rays is in the range of 70 to 130 ° C, preferably 80 to 120 ° C. Here, if the surface temperature is lower than 70 ° C., it is not preferable because not only a long time is required for curing the laminated coating film but also the coating film may be insufficiently cured. In addition, if the surface temperature is higher than 130 ° C., the plastic lens base material may be deformed to damage the base material.

  When the far-infrared ray is irradiated on the laminated coating film under the above conditions, the laminated coating film (that is, the hard coat layer film coating film and the antireflection layer film coating film) is completely cured in a short time without unevenness of curing. It can be cured. The reason why such an effect can be exerted is that, as described above, at least a polycarboxylic acid compound such as polycarboxylic acid or polycarboxylic acid anhydride is contained in the pre-cured coating film. .

Furthermore, the laminated coating film thus obtained has not only excellent adhesion between the coating films, but also excellent properties such as heat resistance and impact resistance.
Moreover, depending on the case, before irradiating a far-infrared ray to the said laminated coating film, you may perform preliminary hardening of the coating film obtained by apply | coating the said coating composition for antireflection layer film formation. In this preliminary curing, as in the case of the hard coat layer film, the coating film is exposed to a hot air atmosphere or a circulating hot air atmosphere, and heat-treated at a temperature of 60 to 110 ° C. for 3 to 30 minutes. Can be done by. However, in the present invention, such preliminary curing is not necessarily performed.

  However, when a water repellent coating layer film is further formed on the surface of the coating film, the coating film is pre-cured and the resulting pre-cured coating film surface is formed on the surface of the water repellent coating layer film. It is preferable to apply a coating composition. The method for forming this water repellent coating layer film and others will be described in detail below.

  The thickness of the upper coating film (that is, the antireflection layer film) constituting the laminated coating film thus obtained varies depending on the required interference color, but is 0.07 to 0.13 μm, preferably 0.8. It is desirable to be in the range of 08 to 0.12 μm. Further, the refractive index of the coating film (antireflection layer film) varies depending on the refractive index of the silica-based fine particles contained in the coating composition for forming the antireflection layer film, the content thereof, etc. It is desirable to be in the range of ˜1.48, preferably 1.33 to 1.40. However, as for the refractive index of this coating film (antireflection layer film), an antireflection effect can be expected if there is a refractive index difference of 0.1 or more with the refractive index of the hard coat layer film constituting the laminated coating film. Therefore, the type of silica-based fine particles (for example, hollow silica-based fine particles) is selected so that the refractive index of the coating film is 0.1 or more, preferably about 0.15 to 0.2 lower than the refractive index of the hard coat layer film. While selecting, it is necessary to adjust the content appropriately. In the case of this coating film (antireflection layer film), the interference vortex does not appear even if the refractive index is different from the refractive index of the plastic lens substrate. .

As a result, a plastic lens having the characteristics according to the present invention is manufactured.
Next, the water repellent coating layer film forming step and the primer layer film forming step employed in the present invention as necessary will be described. However, the formation of the water repellent coating layer film and the primer layer film is not necessarily required in the present invention.

[Formation of water repellent coating layer film]
In this step, a water repellent coating layer film is further formed on the surface of the antireflection layer film.
More specifically, in this step, the coating film obtained in the step (3) is pre-cured by heat treatment for 3 to 30 minutes at a temperature of 60 to 110 ° C. It is preferable to form the water-repellent coat layer film by applying a coating composition for forming a water-repellent coat layer film further containing a fluorine-based compound or a hydrolyzate thereof on the film surface. Here, the preliminary curing of the coating film (antireflection layer film) means a state where the coating film is not completely cured, and more specifically, the coating film is dry to the touch (touched with a finger and dried). This means a state that can be confirmed. (In the second plastic lens described below, the pre-curing operation may be referred to as “step (3a)” and the coating operation may be referred to as “step (3b)”.)
The fluorine compound is not particularly limited, but it is preferable to use a fluorosilane compound having a hydrolyzable group. More specifically, the chemical formula CF ₃ (CF ₂ ) _n (CH ₂ ) ₂ Si (OC ₂ H ₅ ) ₃ (n = 2 to 16), (CH ₃ O) ₃ Si— (CH ₂ ) ₂ (CF ₂ ) Fluorine compounds represented by n (CH ₂ ) ₂ Si (OCH ₃ ) (n = 4 to 8) and the like, hydrolysates thereof, and the like. Among these, from the viewpoint of antifouling property, water repellency, etc., it is preferable to use the fluorine compound with n = 6 or more.

  The water-repellent coating layer film-forming coating composition preferably contains a fluorinated organic solvent for dispersing the fluorinated compound (including a hydrolyzate thereof). Specific examples include perfluorohexane, perfluoromethylcyclohexane, perfluoromethylcyclohexane, perfluoro-1,3-dimethylcyclohexane, and the like. Among these, it is preferable to use perfluorohexane from the viewpoint of wettability.

Furthermore, an organic solvent that can be mixed with the fluorine-containing organic solvent can be used in combination.
Moreover, it is preferable that the said water-repellent coating layer film-forming coating composition contains the said fluorine-type compound or its hydrolyzate in the range of 0.1 to 3 weight%.

Next, a method for forming the water repellent coating layer film will be described as follows.
As described above, the coating composition for forming a water-repellent coating layer film is a coating film (antireflection layer) preliminarily cured by heat treatment for 3 to 30 minutes at a temperature of 60 to 110 ° C. Is applied to the surface of the film using a conventionally known coating method selected from a dipping method, a spin coating method, a spray coating method, an inkjet coating method, and the like. In this case, when the coating composition for forming the water-repellent coating layer film is applied to the surface of the coating film (antireflection layer film) that has not been pre-cured using the dipping method, the coating composition for forming the water-repellent coating layer film is used. This is not preferable because the coating composition for forming an antireflection layer film applied on the base material melts into the pot containing the composition. Furthermore, it is not preferable to apply the coating using a spin coating method or the like because the coating composition for forming a water repellent coating layer film and the coating composition for forming an antireflection layer film are mixed.

  Here, the coating composition for forming the water-repellent coating layer film is composed of the amount of hydroxyl group (.OH) present on the surface of the coating film (antireflection layer film) and the fluorine-based compound contained in the coating composition. Since the adhesion amount varies depending on the type and amount, it is preferable to determine the application amount by experiment. It is preferable to apply at a pulling rate of minutes.

Thus, the coating film obtained by applying the coating composition for forming a water repellent coating layer film is cured by irradiating the coating film with far infrared rays under the conditions shown in the step (4). be able to. In this case, the coating film obtained by applying the coating composition for forming a water repellent coating layer film may be precured before irradiating far infrared rays. Here, the preliminary curing of the coating film (water repellent coating layer film) means a state in which the coating film is not completely cured, and more specifically, the coating film is dry to the touch (touched with a finger to dry). It means that it can be confirmed). In addition, pre-curing of this coating film exposes the said coating film to a hot-air atmosphere or a circulating hot-air atmosphere similarly to the case of the said antireflection layer film, and is 1 minute-5 minutes on 40-60 degreeC temperature conditions. It can be performed by heat treatment. However, in the present invention, such preliminary curing is not necessarily performed.

  The thickness of the coating film (water-repellent coat layer film) thus obtained varies depending on the solid content contained in the coating composition for forming the water-repellent coat layer film, but is in the range of 1 to 10 nm. It is preferable that it exists in.

  Thereby, the plastic lens which has a coating film excellent in water repellency is obtained. Furthermore, by applying this coating film, a plastic lens having excellent antifouling properties and scratch resistance can be obtained.

[Formation of primer layer film]
In this step, a primer layer film is further formed between the plastic lens substrate and the hard coat layer film. More specifically, the primer layer is formed by applying a primer layer film-forming coating composition containing an organic resin compound and metal oxide fine particles onto the plastic lens substrate and curing it. Is done by.

  Further, the organic resin compound used for preparing the primer layer film-forming coating composition includes a thermosetting organic resin and a thermoplastic organic resin, and more specifically, as follows. .

The thermosetting organic resin is preferably at least one selected from urethane resins, epoxy resins, and melamine resins.
Here, examples of the urethane-based resin include a reaction product of a block-type polyisocyanate such as hexamethylene diisocyanate and an active hydrogen-containing compound such as polyester polyol and polyether polyol, and the epoxy resin includes Examples include polyalkylene ether-modified epoxy resins and epoxy group-containing compounds in which a flexible skeleton (soft segment) is introduced into the molecular chain. Further, examples of the melamine resins include etherified methylol melamine, polyester polyol, and polyether polyol. And a cured product. Among these, it is preferable to use a urethane-based resin that is a cured product of a block type isocyanate and a polyol. Moreover, these thermosetting organic resins may use not only one type but also two or more types.

The thermoplastic organic resin is preferably at least one selected from acrylic resins, urethane resins, and ester resins.
Here, examples of the acrylic resin include an aqueous emulsion obtained from a (meth) acrylic acid alkyl ester monomer and a polymer emulsion obtained by copolymerizing the monomer with styrene, acrylonitrile and the like, and the urethane resin. As an example of the polyester resin, an aqueous emulsion obtained by reacting a polyol compound such as polyester polyol, polyether polyol, or polycarbonate polyol with a polyisocyanate is used. Further, as the ester resin, for example, a hard segment may be a polyester or a soft segment. Examples thereof include water-dispersed elastomers of multiblock copolymers using polyether or polyester. Among these, it is preferable to use a water-dispersed urethane resin obtained from polyester polyol or polyether polyol and polyisocyanate. Moreover, these thermoplastic organic resins may use not only one type but also two or more types.

  The metal oxide fine particles used for preparing the primer layer film-forming coating composition include those described in the preparation of the hard coat layer film-forming coating composition.

  More specifically, oxide fine particles of at least one metal element selected from titanium, iron, zinc, tungsten, tin, tantalum, zirconium, antimony, niobium, indium, cerium, silicon, aluminum, yttrium, lead and molybdenum And composite oxide fine particles, and further, a core-shell type metal oxide in which the surface of the fine particles is coated with an oxide or composite oxide of at least one metal element selected from silicon, zirconium, antimony, tin and aluminum Examples include fine particles. Further, these metal oxide fine particles may be used in a mixture of not only one type but also two or more types.

  Further, the metal oxide fine particles have a refractive index of 1.52 to 2.70, preferably 1.60 to 2.60, as in the preparation of the coating composition for forming a hard coat layer film. It is desirable to use those having an average particle size of 7 to 60 nm, preferably 8 to 30 nm.

  Further, when the metal oxide fine particles are present in the state of a water-dispersed sol, when preparing the primer layer film-forming coating composition, it is used in advance in a solvent substitution step or the like to obtain an organic solvent-dispersed sol. Is often necessary. In this case, the surface of the metal oxide fine particles is treated with a surface treatment agent such as an organosilicon compound such as a silane coupling agent or an amine compound in order to hydrophobize the surface of the metal oxide fine particles before being subjected to the solvent replacement step. It is desirable to keep it. Therefore, the metal oxide fine particles used here may be particles that have been surface-treated in advance using a surface treatment agent such as an organosilicon compound or an amine compound.

  Furthermore, it is desirable that the primer layer film-forming coating composition contains a solvent for dispersing the above components, that is, the organic resin compound and the metal oxide fine particles. Specific examples of such solvents include water, alcohols such as methanol, ethanol and propanol, ketones such as methyl ethyl ketone and acetyl acetone, esters such as ethyl acetate and butyl acetate, cellosolves such as ethyl cellosolve and butyl cellosolve, propylene And ethers such as glycol monomethyl ether. Among these, when using a thermosetting resin, ethyl cellosolve, butyl cellosolve, and propylene glycol monomethyl ether are preferable from the viewpoint of compatibility with the thermosetting resin, and when using a thermoplastic emulsion resin, From the viewpoint of the dispersibility of the plastic emulsion resin, it is preferable to use water or methanol. Moreover, this solvent may contain not only one type but also two or more types (for example, water and methanol) as long as they are compatible with each other.

  Here, the solvent varies depending on the type and content of the organic resin compound and the metal oxide fine particles, and also the desired thickness of the coating film (primer layer film), etc. The coating composition preferably contains 60 to 95% by weight.

  The mixing ratio of the organic resin compound and the metal oxide fine particles (including those subjected to surface treatment) depends on the type of the organic resin compound and the metal oxide fine particles, and also the desired coating film (primer layer film). ), The weight ratio (M / N) is 30/70 to 90/10, when the organic resin compound is represented by M and the metal oxide fine particles are represented by N. Preferably it is in the range of 40/60 to 80/20. Here, when the weight ratio is less than 30/70, when a coating composition for forming a primer layer film containing these components is applied onto a plastic lens substrate, the resulting coating film and the plastic This is not preferable because the adhesion to the lens substrate and, further, the hard coat layer film laminated on the coating film tends to deteriorate. In addition, when the weight ratio is more than 90/10, when a primer layer film-forming coating composition containing these components is applied on a plastic lens substrate, a coating film (primer layer film) obtained therefrom is used. ) Is not preferable because the refractive index may be lower than the desired value.

  In the primer layer film-forming coating composition, a silicone surfactant such as polyoxyalkylene dimethylpolysiloxane or a perfluoroalkylcarboxylic acid is used to improve wettability when applied to a plastic lens substrate. Fluorine surfactants such as acid salts and perfluoroalkylethylene oxide adducts may be included.

  Furthermore, the primer layer film-forming coating composition may contain a benzophenone-based UV absorber, a benzotriazole-based UV absorber, a hindered amine-based light stabilizer, and the like, if necessary.

  Next, a method for preparing the primer layer film-forming coating composition will be specifically described. However, since the preparation method described here shows one aspect thereof, the primer layer film-forming coating composition used in the present invention is not limited to those obtained from these preparation methods.

  (A) When the metal oxide fine particles are present in the form of a water-dispersed sol, the water-dispersed sol is subjected to an ultrafiltration device or the like, and water contained in the water-dispersed sol is methanol, propanol, propylene It is desirable to prepare an organic solvent-dispersed sol containing the metal oxide fine particles by replacing the solvent with an organic solvent such as glycol monomethyl ether. In this case, the metal oxide fine particles are preferably contained in the organic solvent-dispersed sol in an amount of 10 to 40% by weight.

  (B) Next, the organic solvent dispersion sol containing the metal oxide fine particles and the organic resin compound, that is, the thermosetting organic resin or the thermoplastic organic resin are mixed and sufficiently stirred.

Specific examples of the organic resin compound are as described above.
When the organic resin compound is, for example, a water-dispersed urethane elastomer, it can be mixed with the organic solvent-dispersed sol in the form of an aqueous dispersion. However, in the case of an organic resin compound that is not a water dispersion type, it is preferable that the organic resin compound is previously dissolved in an organic solvent and mixed with the organic solvent dispersion sol.

  Here, as the organic solvent, alcohols such as methanol, ethanol and propanol, ketones such as methyl ethyl ketone and acetyl acetone, esters such as ethyl acetate and butyl acetate, cellosolves such as ethyl cellosolve and butyl cellosolve, propylene glycol monomethyl ether Among them, it is preferable to use methanol, propanol, propylene glycol monomethyl ether, etc. from the viewpoints of evaporation rate and solubility.

In this case, the organic resin compound is preferably contained in the dispersion by 3 to 20% by weight.
Furthermore, you may add the said surfactant, the said ultraviolet absorber, etc. in the said coating composition for primer layer film formation as needed. In this case, the surfactant, the ultraviolet absorber, and the like may vary depending on their physical properties, but may be mixed in the mixed solution as they are, or after being dissolved or dispersed in the organic solvent. May be.

Thereby, the coating composition for primer layer film formation used by this invention is prepared.
Next, the method for forming the primer layer film will be described as follows.
The primer layer film-forming coating composition obtained above is formed on the plastic lens substrate using a conventionally known coating method selected from a dipping method, a spin coating method, a spray coating method, an ink jet coating method, and the like. Applied.

  Next, the coating film (primer layer film) formed on the plastic lens substrate needs to be cured by heat treatment for 3 to 30 minutes at a temperature of 60 to 110 ° C. It is preferable to keep the coating film in a pre-cured state. Here, the preliminary curing of the coating film means a state where the coating film is not completely cured, and more specifically, the coating film is dry to the touch (can be confirmed to be dry by touching with a finger). Means the state.

  In addition, as a method for pre-curing the coating film, as in the case of pre-curing the hard coat layer film coating film, (1) the coating film formed on the plastic lens substrate is heated in a hot air atmosphere or There are methods of exposing to a circulating hot air atmosphere or (2) irradiating the coating film with far infrared rays.

The thickness of the coating film (primer layer film) obtained in this manner varies depending on the solid content contained in the primer layer film-forming coating composition, but is preferably 0.3 to 3.0 μm, preferably Is preferably in the range of 0.5 to 2.0 μm. Furthermore, the refractive index of the coating film (primer layer film) varies depending on the type and content of the metal oxide fine particles contained in the hard coat layer film-forming coating composition, but the coating film is completely The refractive index when cured to 1.52 to 1.80, preferably 1.55 to 1.78 is desirable.
Thereby, the plastic lens which has the more outstanding impact resistance can be obtained.

[Plastic lens]
Next, the plastic lens according to the present invention will be described. However, it is not limited to what is described here if it is a plastic lens obtained from said manufacturing method.

  A first plastic lens according to the present invention comprises: (1) a coating composition for forming a hard coat layer film comprising an organic silicon compound (A), metal oxide fine particles and a polycarboxylic acid compound on a plastic lens substrate. (2) The obtained coating film was heat-treated at a temperature of 60 to 110 ° C. for 5 to 30 minutes to pre-cure the coating film. An antireflection layer film-forming coating composition containing an organosilicon compound (B) and silica fine particles is applied to the surface of the cured coating film, and (4) a wavelength of 3 to 20 μm is applied to the obtained multilayer coating film. The hard coat layer film and the antireflection layer film are formed on the plastic lens substrate by irradiating the far infrared ray having 5-30 minutes to cure the laminated coating film.

  The second plastic lens according to the present invention is: (1) a paint for forming a hard coat layer film comprising an organosilicon compound (A), metal oxide fine particles and a polycarboxylic acid compound on a plastic lens substrate. The composition was applied, (2) the obtained coating film was heat-treated for 5 to 30 minutes at a temperature of 60 to 110 ° C., and the coating film was pre-cured to obtain (3). A coating composition for forming an antireflection layer film containing an organosilicon compound (B) and silica fine particles is applied to the surface of the pre-cured coating film, and (3a) the obtained coating film is subjected to a temperature condition of 60 to 110 ° C. (3b) A coating composition for water repellent coating treatment containing a fluorine-based compound or a hydrolyzate thereof is applied, 4) A wave of 3 to 20 μm is applied to the obtained laminated coating film. A hard coat layer film, an antireflection layer film, and a water repellent coat layer film are formed on a plastic lens substrate by irradiating far infrared rays having 5 to 30 minutes to cure the laminated coating film. Is.

  As described above, the plastic lens substrate is appropriately selected from commercially available products or test supplies having a refractive index in the range of 1.49 to 1.80, preferably 1.60 to 1.74. Can be used. Various plastics processed and manufactured using polystyrene resins, aliphatic allyl resins, aromatic allyl resins, polycarbonate resins, polythiourethane resins, polythioepoxy resins, etc. There is a lens substrate.

  The coating composition for forming a hard coat layer film contains an organosilicon compound (A), metal oxide fine particles and a polycarboxylic acid compound, and details thereof are as described above. Furthermore, the details of the method for pre-curing a coating film obtained by applying such a coating composition for forming a hard coat layer film are as described above.

  Further, the pre-cured coating film (that is, hard coat layer film) thus obtained desirably has a film thickness in the range of 1.0 to 5.0 μm, preferably 1.5 to 3.5 μm. In addition, it is preferable that the refractive index (assuming that the coating film is completely cured) matches or substantially matches the refractive index of the plastic lens substrate.

  The coating composition for forming an antireflection layer film contains an organosilicon compound (B) and silica fine particles, and details thereof are as described above. Furthermore, the details of the method of curing the laminated coating film obtained by applying such a coating composition for forming an antireflection layer film are as described above.

  Further, the upper coating film (that is, the antireflection layer film) constituting the laminated coating film thus obtained has a thickness in the range of 0.07 to 0.13 μm, preferably 0.08 to 0.12 μm. It is desirable that the refractive index be lower than that of the hard coat layer film by 0.1 or more.

  In the second plastic lens described above, the coating composition for forming a water-repellent coat layer film contains a fluorine-based compound or a hydrolyzate thereof, and the details thereof are as described above. Furthermore, the details of the method for curing the coating film obtained by applying such a coating composition for forming a water repellent coating layer film are as described above.

Moreover, it is desirable that the uppermost layer coating film (that is, the water repellent coating layer film) constituting the laminated coating film thus obtained has a film thickness in the range of 1 to 10 nm.
The plastic lens according to the present invention thus obtained is provided with a multilayer coating film having no unevenness of curing on the surface, and the multilayer coating film has heat resistance, impact resistance, adhesion, scratch resistance, and scratch resistance. Excellent performance in abrasion, weather resistance, and fading resistance.

The second plastic lens subjected to the water repellent coating treatment has excellent characteristics in terms of water repellency and antifouling properties in addition to the above characteristics.
Moreover, it is preferable that the said plastic lens further provides a primer layer film | membrane between the said plastic lens base material and the said hard-coat layer film | membrane. Here, the primer layer film is a coating containing the organic resin compound (that is, at least one organic resin compound selected from the thermosetting organic resin and the thermoplastic organic resin) and the metal oxide fine particles. It is a cured film obtained by curing the film, and the film thickness is desirably in the range of 0.3 to 3.0 μm, preferably 0.5 to 2.0 μm.

  Note that the plastic lens provided with such a primer layer film has a performance superior in impact resistance as compared with the above.

[Measuring method]
Next, the measurement methods and evaluation test methods used in the examples and others of the present invention will be specifically described as follows.

(1) Average particle diameter of particles Solid content prepared by mixing 19.85 g of pure water with 0.15 g of an aqueous dispersion sol (solid content 20% by weight) of the metal oxide fine particles having a nano-sized particle size. A sample having a content of 0.15% was placed in a quartz cell having a length of 1 cm, a width of 1 cm, and a height of 5 cm, and an ultrafine particle size analyzer by dynamic light scattering method (model ELS-Z2 manufactured by Otsuka Electronics Co., Ltd.). ) To measure the particle size distribution of the particle group. In addition, the average particle diameter as used in the field of this invention shows the value computed by cumulant analysis of this measurement result. However, the average particle size of the particles obtained from the particle size distribution of the fine particles measured by the dynamic light scattering method using the ultrafine particle size analyzer is obtained from a TEM photograph of the fine particles taken with a transmission electron microscope. It was found that the average particle diameter of the obtained particles is about 3 times as large. Therefore, the average particle size of the fine particles defined in the present invention is different from the average particle size obtained by other measurement methods.

(2) Refractive Index of Particles A water-dispersed sol or organic solvent-dispersed sol containing the metal oxide fine particles is subjected to an evaporator to evaporate the dispersion medium, and then dried at a temperature of 120 ° C. to obtain a dry powder. Next, 2 to 3 drops of a standard solution reagent having a known refractive index is dropped on a glass substrate, and a dry powder of the metal oxide fine particles is mixed with the drop to prepare a mixed solution. This operation is performed using standard liquid reagents having various refractive indexes (Cargill standard refractive index liquid manufactured by MORITEX), and the refractive index of the standard liquid reagent when the mixed solution becomes transparent is the refractive index of the particles. And
Incidentally, this measuring method is suitable for measuring the refractive index of a particle group having a refractive index of 1.0 to 2.31.

(3) Appearance of coating film (test to observe the degree of interference fringes)
A fluorescent lamp “trade name: Mellow 5N” (manufactured by Toshiba Lighting & Technology Co., Ltd., a three-wavelength daylight white fluorescent lamp) is mounted in a box whose inner wall is black, and the light from the fluorescent lamp is formed on the sample substrate. Reflection is made on the surface of the coating film, and the generation of rainbow patterns (interference fringes) due to light interference is visually confirmed, and evaluated according to the following criteria.
S: There are almost no interference fringes.
A: Interference fringes are not noticeable.
B: Although interference fringes are observed, they are within an allowable range.
C: Interference fringes are conspicuous.
D: There are glaring interference fringes.

(4) Abrasion resistance test of coating film The surface of the laminated coating film formed on the sample substrate is manually rubbed with Bonstar Steel Wool # 0000 (manufactured by Nippon Steel Wool Co., Ltd.), and the degree of scratches is visually observed. Judge and evaluate according to the following criteria.
A: There is almost no scratch.
B: Some scratches enter.
C: There are considerable scratches.
D: Scratches appear on almost the entire surface of the rubbed area.

(5) Coating film reflection test (determination of antireflection properties)
USPM-RU manufactured by Olympus Optical Co., Ltd. was used to measure the reflectance in the visible light region, and the lowest reflectance (bottom reflectance) was used as the reflectance.

(6) Adhesion test of coating film The surface of the laminated coating film formed on the sample substrate is cut with a knife at intervals of 1 mm to form 100 squares of 1 mm square, and the cellophane adhesive tape is strong. After pressing, the plastic lens substrate is rapidly pulled in the direction of 90 degrees with respect to the in-plane direction of the plastic lens substrate, this operation is performed a total of five times, the number of squares that do not peel off is counted, and the following criteria are evaluated.
Good: The number of cells not peeled is 95 or more.
Bad: The number of cells not peeled is less than 95.

(7) Coating dyeing test (test to determine whether the coating is uniformly cured)
In a heat-resistant beaker, add 1 liter of hot water at a temperature of about 90 ° C., and add 3 g of a disperse dye (Dystar Japan Co., Ltd., Daianix Blue AC-E) and 1 g of a dispersant (Senca Co., Ltd., Semol WS100). Stir well. Next, the sample substrate (plastic lens) is immersed for 20 minutes while maintaining the temperature of the mixed solution at about 92 ° C. Next, after taking out the sample substrate and washing it with water, the degree of dyeing of the coating film is visually determined and evaluated according to the following criteria.
○: Dyed evenly or not at all.
(In other words, it shows a state where the coating film is uniformly cured.)
Δ: Dyeing is slightly uneven.
X: Dyeing is uneven.

(8) Water repellency test of coating film Using DM301 manufactured by Kyowa Interface Science Co., Ltd., the static contact angle was measured to evaluate water repellency.
Good: Contact angle of 100 ° or more Poor: Contact angle of less than 100 °

(9) Impact resistance test of coating film A steel ball having a weight of 17 g was dropped from the height of 127 cm onto the center part of the above-mentioned example substrate and comparative example substrate, and evaluated according to the following criteria.
Good: Not cracked Bad: Cracked.

(10) Pot life Various coating compositions used in the present invention (ie, hard coat layer film forming paint, antireflection layer film forming paint, top coat layer film forming paint, primer layer film forming paint, etc. Each of the compositions was placed in a beaker and stored for 4 weeks with stirring in a 10 ° C. temperature atmosphere. Furthermore, these coating compositions are applied onto a plastic lens substrate, and under the same conditions as those shown in the examples and comparative examples of the present invention, a primer layer film (however, formed if necessary) In addition, a laminated coating film was formed in the order of a hard coat layer film, an antireflection layer film, and a top coat layer film.

  Next, the scratch resistance test of each of the obtained laminated coating films was performed under the same conditions as in the “scratch resistance test of the coating film” shown in the above (4). That is, the surface of the laminated coating film was manually rubbed with Bonstar Steel Wool # 0000 (manufactured by Nippon Steel Wool Co., Ltd.), and the degree of the above-mentioned scratch was visually determined to perform the scratch resistance test. It was compared with the results obtained from time to time. As a result, when a result worse than the scratch resistance test result according to the above (4) is obtained, it means that there is a problem (or shortens) in pot life.

[Example]
Hereinafter, the present invention will be specifically described based on examples. However, the present invention is not limited to the scope described in these examples.

(1) Preparation of coating composition for hard coat layer film formation
[Preparation Example 1]
50 g of methanol (manufactured by China Essential Oil Co., Ltd.) was added to 100 g of γ-glycidoxypropyltrimethoxysilane (manufactured by Monmentive Performance Materials Japan GK), and 25 g of 0.01N hydrochloric acid was added dropwise with stirring. . Further, the γ-glycidoxypropyltrimethoxysilane was hydrolyzed by stirring for a whole day and night at room temperature.

  Next, in this mixed solution, 350 g of methanol dispersion “OPTRAIK 1130Z (S-7 / A8)” (manufactured by JGC Catalysts & Chemicals Co., Ltd.) containing core-shell type metal oxide fine particles, as a polycarboxylic acid compound 10 g of trimellitic anhydride (manufactured by Kishida Chemical Co., Ltd.), 2 g of acetylacetone aluminum (manufactured by Kishida Chemical Co., Ltd.) as a curing catalyst, 100 g of propylene glycol monomethyl ether (manufactured by Dow Chemical Japan Co., Ltd.) as an organic solvent, and leveling 0.5 g of a silicone surfactant (manufactured by Toray Dow Corning Co., Ltd., L-7001) as an agent was added, and the mixture was stirred overnight at room temperature. This prepared the coating composition for hard-coat layer film formation (henceforth "hard-coat coating material H1") used for an Example.

The metal oxide fine particle-containing dispersion “OPTRAIK 1130Z (S-7 · A8)” is a composite oxide fine particle containing titanium and zirconium (TiO ₂ / ZrO ₂ = 51. 19) core-shell type metal oxide fine particles having a surface coated with a composite oxide of silicon and zirconium (coating / nuclear particles = 4.88 based on oxide equivalent weight) Further, metal oxide fine particles having an average particle diameter of 9 μm, the surfaces of which are treated with tetraethoxysilane, are dispersed in methanol at a concentration of 30% by weight.

[Preparation Example 2]
90 g of γ-glycidoxypropyltrimethoxysilane (manufactured by Monmentive Performance Materials Japan GK) and 20 g of tetraethoxysilane (manufactured by Kishida Chemical Co., Ltd.) are added with 50 g of methanol (Chinese Essential Oil Co., Ltd.). While stirring, 40 g of 0.01N hydrochloric acid was added dropwise. Further, the γ-glycidoxypropyltrimethoxysilane and the tetraethoxysilane were hydrolyzed by stirring for a whole day and night at room temperature.

Next, 190 g of a methanol dispersion “OPTRAICK 1130Z (S-7 / A8)” (manufactured by JGC Catalysts & Chemicals Co., Ltd.) containing core-shell type metal oxide fine particles in this mixed solution, as a polycarboxylic acid compound 1,2,4,5 benzenetetracarboxylic acid (manufactured by Kishida Chemical Co., Ltd.) 15 g, dicyandiamide (manufactured by Kishida Chemical Co., Ltd.) 2 g as a curing catalyst, propylene glycol monomethyl ether (Dow Chemical Japan Co., Ltd.) as an organic solvent 100 g) and 0.5 g of a silicone-based surfactant (manufactured by Toray Dow Corning Co., Ltd., L-7001) as a leveling agent were added and stirred at room temperature all day and night. This prepared the coating composition for hard-coat layer film formation (henceforth "the hard-coat coating material H2") used for an Example.
The details of the metal oxide fine particle-containing dispersion “Optlake 1130Z (S-7 · A8)” are as described above.

[Preparation Example 3]
50 g of methanol (Chinese Essential Oil Co., Ltd.) was added to 100 g of γ-glycidoxypropyltrimethoxysilane (manufactured by Monmentive Performance Materials Japan GK), and 25 g of 0.01N hydrochloric acid was added dropwise with stirring. Further, the γ-glycidoxypropyltrimethoxysilane was hydrolyzed by stirring for a whole day and night at room temperature.

Next, in this mixed solution, 350 g of methanol dispersion “OPTRAIK 1130Z (S-7 / A8)” (manufactured by JGC Catalysts & Chemicals Co., Ltd.) containing core-shell type metal oxide fine particles, acetylacetone aluminum as a curing catalyst 2 g (manufactured by Kishida Chemical Co., Ltd.), 100 g of propylene glycol monomethyl ether (manufactured by Dow Chemical Japan Co., Ltd.) as an organic solvent, and a silicone surfactant (manufactured by Toray Dow Corning Co., Ltd., L) as a leveling agent -7001) 0.5g was added and it stirred at room temperature all day and night. This prepared the coating composition for hard-coat layer film formation (henceforth "hard-coat coating material C1") used for a comparative example. (That is, this hard coat paint C1 does not contain a polycarboxylic acid compound.)
The details of the metal oxide fine particle-containing dispersion “Optlake 1130Z (S-7 · A8)” are as described above.

[Preparation Example 4]
The hard coat layer film was stirred under the conditions described in Preparation Example 1 except that the amount of trimellitic anhydride added as the polycarboxylic acid compound in Preparation Example 1 was changed to 1 g, 7 g, 25 g, and 40 g, respectively. Each forming coating composition was prepared. As a result, the coating composition for forming a hard coat layer film used in the examples and comparative examples (hereinafter referred to as “hard coat paint C2”, “hard coat paint H3”, “hard coat paint H4” and “hard coat paint, respectively”). C3 ").

(2) Preparation of coating material for antireflection layer film formation
[Preparation Example 5]
40 g of tetraethoxysilane (manufactured by Kishida Chemical Co., Ltd.) and 50 g of isopropyl alcohol (manufactured by Kishida Chemical Co., Ltd.) were mixed, and 10 g of 0.1N hydrochloric acid was added dropwise with stirring. Furthermore, the tetraethoxysilane was hydrolyzed by stirring overnight at a temperature of 30 ° C.

  Next, 50 g of an organic solvent dispersion containing hollow silica-based fine particles “Thruria” (manufactured by JGC Catalysts & Chemicals Co., Ltd.) and 500 g of propylene glycol monomethyl ether are added to this mixed solution, and the mixture is stirred at a temperature of 30 ° C. overnight. Aged. Thereafter, 0.1 g of acetylacetone aluminum (made by Kishida Chemical Co., Ltd.) as a curing catalyst and 0.5 g of a silicone-based surfactant (L-7001 made by Toray Dow Corning Co., Ltd.) as a leveling agent were added, The mixture was cooled to a temperature of 10 ° C. and stirred for a whole day and night while maintaining the temperature. This prepared the coating composition for antireflection layer film formation (henceforth "antireflection coating AR1") used by an Example and a comparative example.

  The hollow silica-based fine particle-containing dispersion “Thruria” is obtained by dispersing hollow silica-based fine particles having cavities inside and having an average particle diameter of 60 nm in isopropyl alcohol at a concentration of 20% by weight.

[Preparation Example 6]
15 g of tetraethoxysilane (manufactured by Kishida Chemical Co., Ltd.), 5 g of methyltriethoxysilane (manufactured by Kishida Chemical Co., Ltd.) and 50 g of propylene glycol monomethyl ether (manufactured by Dow Chemical Japan Co., Ltd.) were mixed and stirred while stirring. 10 g of 1N hydrochloric acid was added dropwise. Furthermore, the tetraethoxysilane and the methyltriethoxysilane were hydrolyzed by stirring overnight at a temperature of 30 ° C.

  Next, 80 g of an organic solvent dispersion containing hollow silica-based fine particles “Thruria” (manufactured by JGC Catalysts & Chemicals Co., Ltd.) and 500 g of propylene glycol monomethyl ether (manufactured by Dow Chemical Japan Co., Ltd.) are added to this mixed liquid, and 30 The maturation was carried out by stirring overnight at a temperature of ° C. Thereafter, 0.1 g of acetylacetone aluminum (made by Kishida Chemical Co., Ltd.) as a curing catalyst and 0.5 g of a silicone-based surfactant (L-7001 made by Toray Dow Corning Co., Ltd.) as a leveling agent were added, The mixture was cooled to a temperature of 10 ° C. and stirred for a whole day and night while maintaining the temperature. This prepared the coating composition for antireflection layer film formation (henceforth "antireflection coating AR2") used by an Example and a comparative example.

  The details of the hollow silica-based fine particle-containing dispersion “Thruria” are as described above.

(3) Preparation of paint for water repellent coating treatment (paint for forming topcoat layer film)
[Preparation Example 7]
Fluorine compound of chemical formula CF ₃ (CF ₂ ) ₇ (CH ₂ ) ₂ Si (OC ₂ H ₅ ) ₃ (AY43-158E, manufactured by Toray Dow Corning Co., Ltd.) and fluorine-containing organic solvent (FR manufactured by Shin-Etsu Chemical Co., Ltd.) -THINNER) 500 g was mixed and stirred for 24 hours to prepare a water-repellent coating composition (hereinafter referred to as “water-repellent coating T1”).

(4) Preparation of coating composition for primer layer film formation
[Preparation Example 8]
122 g of commercially available polyurethane emulsion “Superflex 420” (Daiichi Kogyo Seiyaku Co., Ltd.), methanol dispersion containing core / shell type metal oxide fine particles “OPTRAIK 1120Z (S-7 · G)” (JGC) 250 g of Catalyst Chemicals Co., Ltd. and 480 g of methanol (Chinese Essential Oil Co., Ltd.) were added and stirred at room temperature for 1 hour.

  Next, 1.0 g of a silicone surfactant (manufactured by Toray Dow Corning Co., Ltd., L-7001) as a leveling agent was added to the mixed solution, and the mixture was stirred at room temperature all day and night. Thus, a primer layer film-forming coating composition (hereinafter referred to as “primer coating P1”) used in Examples and Comparative Examples was prepared.

The polyurethane emulsion “Superflex 420” is obtained by dispersing a water-dispersed urethane elastomer in water at a concentration of 32% by weight. The metal oxide fine particle-containing dispersion “OPTRAIK 1120Z (S-7 · G)” is a composite oxide fine particle containing titanium and zirconium (TiO ₂ / ZrO ₂ = 51. 19) core-shell type metal oxide fine particles having a surface coated with a composite oxide of silicon and zirconium (coating / nuclear particles = 4.88 based on oxide equivalent weight) In addition, metal oxide fine particles having an average particle diameter of 9 μm whose surface was treated with γ-glycidoxypropyltrimethoxysilane were dispersed in methanol at a concentration of 20% by weight.

(5) Pretreatment of plastic lens substrate
[Preparation Example 9]
From the commercially available products shown below, the plastic lens substrates of the number required for testing and evaluation in Examples and Comparative Examples were prepared.
(A) Plastic lens substrate A having a refractive index of 1.60 (this lens substrate is obtained by polymerizing a monomer having a product name “MR-8” manufactured by Mitsui Chemicals, Inc.)
(B) Plastic lens base material B having a refractive index of 1.67 (this lens base material is obtained by polymerizing a monomer having a product name “MR-7” manufactured by Mitsui Chemicals, Inc.)
Subsequently, these plastic lens substrates were etched by being immersed in an aqueous potassium hydroxide solution (KOH concentration: 10% by weight) maintained at a temperature of 40 ° C. for 2 minutes. Further, these lens base materials were taken out from the aqueous solution, washed with water, and then sufficiently dried.

[Example 1]
The plastic lens base material B (refractive index: 1.67) obtained in Preparation Example 9 is immersed in the pot containing the hard coat paint H1 obtained in Preparation Example 1, and the dipping method is used to further immerse the plastic lens base material B (refractive index: 1.67). The plastic lens substrate B was pulled up at a speed of 120 mm / min, and the hard coat paint H1 was applied to the surface of the substrate.

  Next, the plastic lens substrate B coated with the hard coat paint H1 is placed in a hot air circulating furnace (ST-120, manufactured by Espec Co., Ltd.) to which hot air at 100 ° C. is circulated and supplied. The coating film formed on B was heated in a temperature atmosphere of 100 ° C. for 10 minutes to pre-cure the coating film.

  Next, the plastic lens base material B having the precured coating film is immersed in the pot containing the antireflection coating AR1 obtained in Preparation Example 5, and the plastic lens is further dipped. The base material B was pulled up at a speed of 24 mm / min, and the antireflection paint AR1 was applied to the surface of the base material.

  Next, a far-infrared ceramic in which two plastic lens base materials B each having a laminated coating film in which the anti-reflection coating AR1 is applied on the coating film that has been pre-cured by applying the hard coating paint H1 are installed on the top and bottom. Placed between heaters (S-I type, manufactured by Sakaguchi Electric Heat Co., Ltd.), fixed horizontally, and left to dry in a room temperature atmosphere for 30 minutes, then formed on the plastic lens substrate B Far infrared rays were irradiated for 15 minutes from a direction perpendicular to the coated film surface. At this time, irradiation with far infrared rays was performed so that the surface temperature of the coating film was 110 ° C.

As a result, a plastic lens (hereinafter referred to as “plastic lens A-1”) having a laminated coating film composed of a hard coat layer film and an antireflection layer film on its surface was obtained.
Next, with respect to the obtained plastic lens A-1, based on the above measurement method, the appearance of the multilayer coating film formed on the plastic lens substrate (observation of interference vortex), scratch resistance, adhesion, antireflection Property, dyeability (uniform curing), water repellency and impact resistance were observed or measured. The results are shown in Table 1.

[Example 2]
The plastic lens substrate B (refractive index: 1.67) obtained in Preparation Example 9 is immersed in the pot containing the hard coat paint H1 obtained in Preparation Example 1, and the dipping method is used to further immerse the plastic lens base material B (refractive index: 1.67). The plastic lens substrate B was pulled up at a speed of 120 mm / min, and the hard coat paint H1 was applied to the surface of the substrate.

  Next, the plastic lens substrate B coated with the hard coat paint H1 is placed in a hot air circulating furnace (ST-120, manufactured by Espec Co., Ltd.) to which hot air at 100 ° C. is circulated and supplied. The coating film formed on B was heated in a temperature atmosphere of 100 ° C. for 10 minutes to pre-cure the coating film.

  Next, the plastic lens base material B having the precured coating film is immersed in the pot containing the antireflection coating AR1 obtained in Preparation Example 5, and the plastic lens is further dipped. The base material B was pulled up at a speed of 24 mm / min, and the antireflection paint AR1 was applied to the surface of the base material.

  Next, the plastic lens base material B coated with the antireflection coating AR1 is placed in a hot air circulating furnace (ST-120 manufactured by Espec Co., Ltd.) in which hot air of 80 ° C. is circulated and supplied. The coating film formed on B was heated at 80 ° C. for 10 minutes to pre-cure the coating film.

  Next, the plastic lens substrate B having the coating film preliminarily cured as described above is immersed in the pot containing the water repellent coating material T1 obtained in Preparation Example 7, and the plastic is further removed using a dipping method. The lens substrate B was pulled up at a speed of 200 mm / min, and the water repellent coating material T1 was applied to the surface of the substrate.

  Next, the plastic lens base material B coated with the water repellent coating material T1 is placed in a hot air circulating furnace (ST-120, manufactured by Espec Co., Ltd.) to which hot air of 80 ° C. is circulated and supplied. The coating film formed on the substrate B was heated for 10 minutes in a temperature atmosphere of 80 ° C. to preliminarily cure the coating film.

  Next, a plastic lens base material B having a laminated coating film in which the hard coat paint H1, the antireflection paint AR1, and the water repellent coat paint T1 are sequentially applied and pre-cured is placed in two up and down directions. Placed between the far-infrared ceramic heater (S-I type, manufactured by Sakaguchi Electric Heat Co., Ltd.) installed in the machine and fixed horizontally, and perpendicular to the coating film surface formed on the plastic lens substrate B Far-infrared rays were irradiated for 15 minutes from the direction. At this time, irradiation with far infrared rays was performed so that the surface temperature of the coating film was 110 ° C.

  As a result, a plastic lens (hereinafter referred to as “plastic lens A-2”) having a laminated coating film comprising a hard coat layer film, an antireflection layer film and a water repellent coat layer film on its surface was obtained.

  Next, with respect to the obtained plastic lens A-2, based on the above measurement method, the appearance of the laminated coating film formed on the plastic lens substrate (observation of interference vortex), scratch resistance, adhesion, antireflection Property, dyeability (uniform curing), water repellency and impact resistance were observed or measured. The results are shown in Table 1.

[Example 3]
The plastic lens substrate A (refractive index: 1.60) obtained in Preparation Example 9 is immersed in the pot containing the hard coat paint H2 obtained in Preparation Example 2, and the dipping method is used to further immerse the plastic lens base material A (refractive index: 1.60). The plastic lens substrate A was pulled up at a speed of 120 mm / min, and the hard coat paint H2 was applied to the surface of the substrate.

  Next, the plastic lens substrate A coated with the hard coat paint H2 is placed in a hot air circulating furnace (ST-120 manufactured by Espec Co., Ltd.) to which hot air of 100 ° C. is circulated and supplied. The coating film formed on A was heated in a temperature atmosphere of 100 ° C. for 10 minutes to pre-cure the coating film.

  Next, the plastic lens substrate A having the precured coating film is immersed in the pot containing the antireflection coating AR2 obtained in Preparation Example 6, and the plastic lens is further dipped. The substrate A was pulled up at a speed of 24 mm / min, and the antireflection coating AR2 was applied to the surface of the substrate.

  Next, the plastic lens substrate A coated with the anti-reflection coating AR2 is placed in a hot air circulating furnace (ST-120, manufactured by Espec Corp.) to which hot air of 80 ° C. is circulated and supplied. The coating film formed on A was heated in a temperature atmosphere of 80 ° C. for 10 minutes to pre-cure the coating film.

  Next, the plastic lens substrate A having the pre-cured coating film is immersed in the pot containing the water repellent coating material T1 obtained in Preparation Example 7, and the plastic is further removed using a dipping method. The lens substrate A was pulled up at a speed of 200 mm / min, and the water repellent coating material T1 was applied to the surface of the substrate.

  Next, the plastic lens substrate A coated with the water repellent coating material T1 is placed in a hot air circulating furnace (ST-120, manufactured by Espec Co., Ltd.) to which hot air of 80 ° C. is circulated and supplied. The coating film formed on the substrate A was heated for 10 minutes in a temperature atmosphere of 80 ° C. to pre-cure the coating film.

  Next, a plastic lens substrate A having a laminated coating film in which the hard coat paint H2, the antireflection paint AR2 and the water repellent coat paint T1 are sequentially applied and preliminarily cured is placed up and down. It is placed between the far-infrared ceramic heater (S-I type, manufactured by Sakaguchi Electric Heat Co., Ltd.) installed in the machine and fixed horizontally, and further perpendicular to the coating film surface formed on the plastic lens substrate A Far-infrared rays were irradiated from the direction for 20 minutes. The far-infrared irradiation at this time was performed so that the surface temperature of the coating film was 100 ° C.

  As a result, a plastic lens (hereinafter referred to as “plastic lens A-3”) having a laminated coating film comprising a hard coat layer film, an antireflection layer film and a water repellent coat layer film on its surface was obtained.

  Next, with respect to the obtained plastic lens A-3, based on the above measurement method, the appearance of the multilayer coating film formed on the plastic lens substrate (observation of interference vortex), scratch resistance, adhesion, antireflection Property, dyeability (uniform curing), water repellency and impact resistance were observed or measured. The results are shown in Table 1.

[Example 4]
The plastic lens base material B (refractive index: 1.67) obtained in Preparation Example 9 is immersed in the pot containing the primer coating P1 obtained in Preparation Example 8, and the plastic is further removed using a dipping method. The lens substrate B was pulled up at a speed of 120 mm / min, and the primer coating P1 was applied to the surface of the substrate.

  Next, the plastic lens substrate B coated with the primer coating P1 is placed in a hot air circulation furnace (ST-120, manufactured by Espec Co., Ltd.) in which hot air of 75 ° C. is circulated and supplied. The coating film formed above was heated in a temperature atmosphere of 75 ° C. for 10 minutes to pre-cure the coating film.

  Next, the plastic lens base material B having the precured coating film is immersed in the pot containing the hard coat paint H1 obtained in Preparation Example 1, and the plastic lens is further dipped. The base material B was pulled up at a speed of 120 mm / min, and the hard coat paint H1 was applied to the surface of the base material.

  Next, the plastic lens substrate B coated with the hard coat paint H1 is placed in a hot air circulating furnace (ST-120, manufactured by Espec Co., Ltd.) to which hot air at 100 ° C. is circulated and supplied. The coating film formed on B was heated in a temperature atmosphere of 100 ° C. for 10 minutes to pre-cure the coating film.

  Next, the plastic lens base material B having the precured coating film is immersed in the pot containing the antireflection coating AR1 obtained in Preparation Example 5, and the plastic lens is further dipped. The base material B was pulled up at a speed of 24 mm / min, and the antireflection paint AR1 was applied to the surface of the base material.

  Next, the plastic lens base material B coated with the antireflection coating AR1 is placed in a hot air circulating furnace (ST-120 manufactured by Espec Co., Ltd.) in which hot air of 80 ° C. is circulated and supplied. The coating film formed on B was heated at 80 ° C. for 10 minutes to pre-cure the coating film.

  Next, the plastic lens substrate B having the coating film preliminarily cured as described above is immersed in the pot containing the water repellent coating material T1 obtained in Preparation Example 7, and the plastic is further removed using a dipping method. The lens substrate B was pulled up at a speed of 200 mm / min, and the water repellent coating material T1 was applied to the surface of the substrate.

  Next, the plastic lens base material B coated with the water repellent coating material T1 is placed in a hot air circulating furnace (ST-120, manufactured by Espec Co., Ltd.) to which hot air of 80 ° C. is circulated and supplied. The coating film formed on the substrate B was heated for 10 minutes in a temperature atmosphere of 80 ° C. to preliminarily cure the coating film.

  Next, a plastic lens substrate having a multilayer coating film in which the primer coating P1, the hard coating H1, the antireflection coating AR1, and the water repellent coating T1 are sequentially applied and precured. B is placed between two far infrared ceramic heaters (Sakaguchi Electric Heat Co., Ltd., SI type) installed at the top and bottom, fixed horizontally, and further coated on the plastic lens substrate B. Far infrared rays were irradiated for 7 minutes from a direction perpendicular to the film surface. At this time, irradiation with far infrared rays was performed so that the surface temperature of the coating film was 120 ° C.

  As a result, a plastic lens (hereinafter referred to as “plastic lens A-4”) having a multilayer coating film composed of a primer layer film, a hard coat layer film, an antireflection layer film and a water repellent coat layer film was obtained.

  Next, with respect to the obtained plastic lens A-4, based on the above measurement method, the appearance of the laminated coating film formed on the plastic lens substrate (observation of interference vortex), scratch resistance, adhesion, antireflection Property, dyeability (uniform curing), water repellency and impact resistance were observed or measured. The results are shown in Table 1.

[比較例１]
調製例３で得られたハードコート用塗料Ｃ１（この塗料には、ポリカルボン酸化合物が含まれていない。）を入れたポット中に、調製例９で得られたプラスチックレンズ基材Ｂ（屈折率：１．６７）を浸漬し、さらにディッピング法を用いて該プラスチックレンズ基材Ｂを１２０ｍｍ/ｍｉｎの速度で引き上げて、該基材の表面に前記ハードコート用塗料Ｈ１を塗布した。

[Comparative Example 1]
In the pot containing the hard coat paint C1 obtained in Preparation Example 3 (this paint does not contain a polycarboxylic acid compound), the plastic lens substrate B obtained in Preparation Example 9 (refraction) Then, the plastic lens base material B was pulled up at a speed of 120 mm / min using a dipping method, and the hard coat paint H1 was applied to the surface of the base material.

  Next, the plastic lens substrate B coated with the hard coat paint C1 is placed in a hot air circulating furnace (ST-120, manufactured by Espec Co., Ltd.) to which hot air of 100 ° C. is circulated and supplied. The coating film formed on B was heated in a temperature atmosphere of 100 ° C. for 10 minutes to pre-cure the coating film.

  Next, the plastic lens base material B having the precured coating film is immersed in the pot containing the antireflection coating AR1 obtained in Preparation Example 5, and the plastic lens is further dipped. The base material B was pulled up at a speed of 24 mm / min, and the antireflection paint AR1 was applied to the surface of the base material.

  Next, the plastic lens base material B coated with the antireflection coating AR1 is placed in a hot air circulating furnace (ST-120 manufactured by Espec Co., Ltd.) in which hot air of 80 ° C. is circulated and supplied. The coating film formed on B was heated at 80 ° C. for 10 minutes to pre-cure the coating film.

  Next, the plastic lens substrate B having the coating film preliminarily cured as described above is immersed in the pot containing the water repellent coating material T1 obtained in Preparation Example 7, and the plastic is further removed using a dipping method. The lens substrate B was pulled up at a speed of 200 mm / min, and the water repellent coating material T1 was applied to the surface of the substrate.

  Next, the plastic lens base material B coated with the water repellent coating material T1 is placed in a hot air circulating furnace (ST-120, manufactured by Espec Co., Ltd.) to which hot air of 80 ° C. is circulated and supplied. The coating film formed on the substrate B was heated for 10 minutes in a temperature atmosphere of 80 ° C. to preliminarily cure the coating film.

  Next, a plastic lens base material B having a laminated coating film in which the hard coat paint C1, the antireflection paint AR1, and the water repellent coat paint T1 are sequentially applied and preliminarily cured is placed up and down two times. Placed between the far-infrared ceramic heater (S-I type, manufactured by Sakaguchi Electric Heat Co., Ltd.) installed in the machine and fixed horizontally, and perpendicular to the coating film surface formed on the plastic lens substrate B Far-infrared rays were irradiated for 15 minutes from the direction. At this time, irradiation with far infrared rays was performed so that the surface temperature of the coating film was 110 ° C.

  As a result, a plastic lens (hereinafter referred to as “plastic lens B-1”) having a laminated coating film comprising a hard coat layer film, an antireflection layer film and a water repellent coat layer film on its surface was obtained.

  Next, with respect to the obtained plastic lens B-1, based on the above measurement method, the appearance of the multilayer coating film formed on the plastic lens substrate (observation of interference vortex), scratch resistance, adhesion, antireflection Property, dyeability (uniform curing), water repellency and impact resistance were observed or measured. The results are shown in Table 2.

[Comparative Example 2]
The plastic lens base material B (refractive index: 1.67) obtained in Preparation Example 9 is immersed in the pot containing the hard coat paint H1 obtained in Preparation Example 1, and the dipping method is used to further immerse the plastic lens base material B (refractive index: 1.67). The plastic lens substrate B was pulled up at a speed of 120 mm / min, and the hard coat paint H1 was applied to the surface of the substrate.

  Next, the plastic lens substrate B coated with the hard coat paint H1 is placed in a hot air circulating furnace (ST-120, manufactured by Espec Co., Ltd.) to which hot air at 100 ° C. is circulated and supplied. The coating film formed on B was heated in a temperature atmosphere of 100 ° C. for 10 minutes to pre-cure the coating film.

  Next, the plastic lens base material B having the precured coating film is immersed in the pot containing the antireflection coating AR1 obtained in Preparation Example 5, and the plastic lens is further dipped. The base material B was pulled up at a speed of 24 mm / min, and the antireflection paint AR1 was applied to the surface of the base material.

  Next, the plastic lens base material B coated with the antireflection coating AR1 is placed in a hot air circulating furnace (ST-120 manufactured by Espec Co., Ltd.) in which hot air of 80 ° C. is circulated and supplied. The coating film formed on B was heated at 80 ° C. for 10 minutes to pre-cure the coating film.

  Next, the plastic lens substrate B having the coating film preliminarily cured as described above is immersed in the pot containing the water repellent coating material T1 obtained in Preparation Example 7, and the plastic is further removed using a dipping method. The lens substrate B was pulled up at a speed of 200 mm / min, and the water repellent coating material T1 was applied to the surface of the substrate.

  Next, the plastic lens base material B coated with the water repellent coating material T1 is placed in a hot air circulating furnace (ST-120, manufactured by Espec Co., Ltd.) to which hot air of 80 ° C. is circulated and supplied. The coating film formed on the substrate B was heated for 10 minutes in a temperature atmosphere of 80 ° C. to preliminarily cure the coating film.

  Next, a plastic lens substrate B having a laminated coating film in which the hard coat paint H1, the antireflection paint AR1, and the water repellent coat paint T1 are sequentially applied and pre-cured is applied at 110 ° C. Put into a hot air circulating furnace (ST-120, manufactured by Espec Co., Ltd.) to which hot air is circulated and heat the laminated coating film formed on the plastic lens substrate B for 15 minutes in a temperature atmosphere of 110 ° C. Then, the laminated coating film was cured. That is, here, the surface temperature of the coating film was set to be around 110 ° C. using hot air of 110 ° C. without using far infrared rays as a heat source for curing the laminated coating film.

  As a result, a plastic lens (hereinafter referred to as “plastic lens B-2”) having a laminated coating film comprising a hard coat layer film, an antireflection layer film and a water repellent coat layer film on its surface was obtained.

  Next, with respect to the obtained plastic lens B-2, based on the above measurement method, the appearance of the multilayer coating film formed on the plastic lens substrate (observation of interference vortex), scratch resistance, adhesion, antireflection Property, dyeability (uniform curing), water repellency and impact resistance were observed or measured. The results are shown in Table 2.

[Comparative Example 3]
The plastic lens substrate A (refractive index: 1.60) obtained in Preparation Example 9 is immersed in the pot containing the hard coat paint H2 obtained in Preparation Example 2, and the dipping method is used to further immerse the plastic lens base material A (refractive index: 1.60). The plastic lens substrate A was pulled up at a speed of 120 mm / min, and the hard coat paint H2 was applied to the surface of the substrate.

  Next, the plastic lens substrate A coated with the hard coat paint H2 is placed in a hot air circulation furnace (ST-120, manufactured by Espec Co., Ltd.) in which hot air of 120 ° C. is circulated and supplied. The coating film formed on A was heated in a temperature atmosphere of 120 ° C. for 20 minutes to cure the coating film. That is, here, the coating film (hard coat layer film) was fully cured.

  Next, the plastic lens substrate A having the above-cured coating film is immersed in the pot containing the antireflection coating AR2 obtained in Preparation Example 6, and the plastic lens is further dipped. The substrate A was pulled up at a speed of 24 mm / min, and the antireflection coating AR2 was applied to the surface of the substrate.

  Next, the plastic lens substrate A coated with the anti-reflection coating AR2 is placed in a hot air circulating furnace (ST-120, manufactured by Espec Corp.) to which hot air of 80 ° C. is circulated and supplied. The coating film formed on A was heated in a temperature atmosphere of 80 ° C. for 10 minutes to pre-cure the coating film.

  Next, the plastic lens substrate A having the pre-cured coating film is immersed in the pot containing the water repellent coating material T1 obtained in Preparation Example 7, and the plastic is further removed using a dipping method. The lens substrate A was pulled up at a speed of 200 mm / min, and the water repellent coating material T1 was applied to the surface of the substrate.

  Next, the plastic lens substrate A coated with the water repellent coating material T1 is placed in a hot air circulating furnace (ST-120, manufactured by Espec Co., Ltd.) to which hot air of 80 ° C. is circulated and supplied. The coating film formed on the substrate A was heated for 10 minutes in a temperature atmosphere of 80 ° C. to pre-cure the coating film.

  Next, a plastic lens substrate A having a multilayer coating film obtained by applying the hard coat paint H2, the antireflection paint AR2 and the water repellent coat paint T1 in this order, followed by main curing or preliminary curing, Placed between two far-infrared ceramic heaters (S-I type, manufactured by Sakaguchi Electric Heat Co., Ltd.) installed on the top and bottom and fixed horizontally, and further on the coating film surface formed on the plastic lens substrate A On the other hand, far-infrared rays were irradiated from a right angle direction for 3 minutes. The far-infrared irradiation at this time was performed so that the surface temperature of the coating film was 100 ° C. That is, here, the far-infrared irradiation amount was small.

  As a result, a plastic lens (hereinafter referred to as “plastic lens B-3”) having a laminated coating film comprising a hard coat layer film, an antireflection layer film and a water repellent coat layer film on its surface was obtained.

  Next, with respect to the obtained plastic lens B-3, based on the above measurement method, the appearance of the multilayer coating film formed on the plastic lens substrate (observation of interference vortex), scratch resistance, adhesion, antireflection Property, dyeability (uniform curing), water repellency and impact resistance were observed or measured. The results are shown in Table 2.

[Comparative Example 4]
The plastic lens base material B (refractive index: 1.67) obtained in Preparation Example 9 is immersed in the pot containing the primer coating P1 obtained in Preparation Example 8, and the plastic is further removed using a dipping method. The lens substrate B was pulled up at a speed of 120 mm / min, and the primer coating P1 was applied to the surface of the substrate.

  Next, the plastic lens substrate B coated with the primer coating P1 is placed in a hot air circulation furnace (ST-120, manufactured by Espec Co., Ltd.) in which hot air of 75 ° C. is circulated and supplied. The coating film formed above was heated in a temperature atmosphere of 75 ° C. for 10 minutes to pre-cure the coating film.

  Next, the plastic lens base material B having the precured coating film is immersed in the pot containing the hard coat paint H1 obtained in Preparation Example 1, and the plastic lens is further dipped. The base material B was pulled up at a speed of 120 mm / min, and the hard coat paint H1 was applied to the surface of the base material.

  Next, the plastic lens substrate B coated with the hard coat paint H1 is placed in a hot air circulation furnace (ST-120, manufactured by Espec Co., Ltd.) to which hot air of 65 ° C. is circulated and supplied. The coating film formed on B was heated in a temperature atmosphere of 65 ° C. for 7 minutes to pre-cure the coating film. That is, here, the preliminary curing of the coating film (hard coat layer film) was not sufficient.

  Next, the plastic lens base material B having the precured coating film is immersed in the pot containing the antireflection coating AR1 obtained in Preparation Example 5, and the plastic lens is further dipped. The base material B was pulled up at a speed of 24 mm / min, and the antireflection paint AR1 was applied to the surface of the base material.

  Next, the plastic lens base material B coated with the antireflection coating AR1 is placed in a hot air circulating furnace (ST-120 manufactured by Espec Co., Ltd.) in which hot air of 80 ° C. is circulated and supplied. The coating film formed on B was heated at 80 ° C. for 10 minutes to pre-cure the coating film.

  Next, the plastic lens substrate B having the coating film preliminarily cured as described above is immersed in the pot containing the water repellent coating material T1 obtained in Preparation Example 7, and the plastic is further removed using a dipping method. The lens substrate B was pulled up at a speed of 200 mm / min, and the water repellent coating material T1 was applied to the surface of the substrate.

  Next, the plastic lens base material B coated with the water repellent coating material T1 is placed in a hot air circulating furnace (ST-120, manufactured by Espec Co., Ltd.) to which hot air of 80 ° C. is circulated and supplied. The coating film formed on the substrate B was heated for 10 minutes in a temperature atmosphere of 80 ° C. to preliminarily cure the coating film.

  Next, a plastic lens substrate having a multilayer coating film in which the primer coating P1, the hard coating H1, the antireflection coating AR1, and the water repellent coating T1 are sequentially applied and precured. B is placed in a hot air circulating furnace (ST-120 manufactured by Espec Corp.) to which hot air of 120 ° C. is circulated and supplied, and the laminated coating film formed on the plastic lens substrate B is heated to a temperature of 120 ° C. The laminated coating film was cured by heating for 7 minutes in an atmosphere. That is, here, the surface temperature of the coating film was set to be around 120 ° C. using hot air at 120 ° C. without using far infrared rays as a heat source for curing the laminated coating film.

  As a result, a plastic lens (hereinafter referred to as “plastic lens B-4”) having a laminated coating film composed of a primer layer film, a hard coat layer film, an antireflection layer film and a water repellent coat layer film on its surface was obtained.

  Next, for the obtained plastic lens B-4, based on the above measurement method, the appearance of the laminated coating film formed on the plastic lens substrate (observation of interference vortex), scratch resistance, adhesion, antireflection Property, dyeability (uniform curing), water repellency and impact resistance were observed or measured. The results are shown in Table 2.

[実施例５〜６および比較例５〜６]
調製例４で得られたハードコート用塗料Ｃ２、ハードコート塗料Ｈ３、ハードコート塗料Ｈ４およびハードコート塗料Ｃ３をそれぞれ入れたポット中に、調製例９で得られたプラスチックレンズ基材Ｂ（屈折率：１．６７）を各１枚ずつ浸漬し、さらにディッピング法を用いて該プラスチックレンズ基材Ｂを１２０ｍｍ/ｍｉｎの速度で引き上げて、該基材の表面に前記ハードコート用塗料Ｃ２、Ｈ３、Ｈ４およびＣ３をそれぞれ塗布した。

[Examples 5-6 and Comparative Examples 5-6]
The plastic lens substrate B (refractive index) obtained in Preparation Example 9 was put in the pot containing the hard coat paint C2, hard coat paint H3, hard coat paint H4, and hard coat paint C3 obtained in Preparation Example 4, respectively. : 1.67) one by one, and using a dipping method, the plastic lens substrate B is pulled up at a speed of 120 mm / min, and the hard coat paints C2, H3, H4 and C3 were applied respectively.

  Next, a hot-air circulating furnace (manufactured by ESPEC Corp., ST-) in which hot air at 100 ° C. is circulated through each of the plastic lens base materials B each coated with the hard coat paints C2, H3, H4 and C3. 120), the coating film formed on the plastic lens substrate B was heated in a temperature atmosphere of 100 ° C. for 10 minutes to pre-cure the coating film.

  Next, the plastic lens base material B having the precured coating film is immersed in the pot containing the antireflection coating AR1 obtained in Preparation Example 5 one by one, and a dipping method is used. The plastic lens base material B was pulled up at a speed of 24 mm / min, and the antireflection coating AR1 was applied to the surface of the base material.

  Next, the plastic lens base material B coated with the antireflection coating AR1 is put in a hot air circulation furnace (Espec Corp., ST-120) in which hot air of 80 ° C. is circulated. The coating film formed on the plastic lens substrate B was heated for 10 minutes in a temperature atmosphere of 80 ° C., and the coating film was pre-cured.

  Next, the plastic lens base material B having the pre-cured coating film is dipped one by one in the pot containing the water repellent coating material T1 obtained in Preparation Example 7, and a dipping method is further performed. The plastic lens substrate B was pulled up at a speed of 200 mm / min, and the water repellent coating material T1 was applied to the surface of the substrate.

  Next, the plastic lens base material B coated with the water repellent coating material T1 is put into a hot air circulating furnace (Espec Corp., ST-120) in which hot air of 80 ° C. is circulated and supplied one by one. The coating film formed on the plastic lens substrate B was heated for 10 minutes in a temperature atmosphere of 80 ° C. to pre-cure the coating film.

  Next, a plastic lens base material having a laminated coating film in which the hard coat paint C2, H3, H4 or C3, the antireflection paint AR1, and the water repellent coat paint T1 are sequentially applied and precured. B is placed between two far infrared panel heaters (manufactured by Sakaguchi Electric Heating Co., Ltd., PH-100), one on each side, and fixed horizontally, and further formed on the plastic lens substrate B Far infrared rays were irradiated for 15 minutes from a direction perpendicular to the coated film surface. At this time, irradiation with far infrared rays was performed so that the surface temperature of the coating film was 110 ° C.

  As a result, four plastic lenses each having a laminated coating film comprising a hard coat layer film, an antireflection layer film and a water repellent coat layer film on the surface (hereinafter referred to as “plastic lens B -5 "," Plastic lens A-5 "," Plastic lens A-6 ", and" Plastic lens B-6 ").

  Next, the obtained plastic lens A-5 (Example 5), plastic lens A-6 (Example 6), plastic lens B-5 (Comparative Example 5) and plastic lens B-6 (Comparative Example 6) Based on the above measurement method, appearance of laminated coating film formed on plastic lens substrate (observation of interference vortex), scratch resistance, adhesion, antireflection, dyeability (uniform curing), water repellency And the impact resistance was observed or measured. The results are shown in Table 3.

Claims (15)

In a method for producing a plastic lens, in which a hard coat layer film is formed on a plastic lens substrate, and an antireflection layer film is further formed on the surface thereof,
(1) A step of applying a hard coat layer film-forming coating composition containing an organosilicon compound (A), metal oxide fine particles and a polycarboxylic acid compound on a plastic lens substrate,
(2) A step of pre-curing the coating film by heat-treating the coating film obtained in the step (1) under a temperature condition of 60 to 110 ° C. for 5 to 30 minutes,
(3) A step of applying a coating composition for forming an antireflection layer film containing an organosilicon compound (B) and silica-based fine particles to the surface of the precured coating film obtained in the step (2), and (4 ) A plastic comprising a step of irradiating the laminated coating film obtained in the step (3) with a far infrared ray having a wavelength of 3 to 20 μm for 5 to 30 minutes to cure the laminated coating film Lens manufacturing method. 2. The plastic lens according to claim 1, wherein the organosilicon compounds (A) and (B) are an organosilicon compound represented by the following general formula (I) and / or a hydrolyzate thereof. Method.
R ¹ _a R ² _b Si (OR ³ ) _{4- (a + b)} (I)
(In the formula, R ¹ is an alkyl group having 1 to 6 carbon atoms, an organic group having 8 or less carbon atoms containing a vinyl group, an organic group having 8 or less carbon atoms containing an epoxy group, and 8 carbon atoms containing a methacryloxy group. The following organic group, an organic group having 1 to 5 carbon atoms containing a mercapto group or an organic group having 1 to 5 carbon atoms containing an amino group, R ² is an alkyl group having 1 to 3 carbon atoms, an alkylene group, A cycloalkyl group, a halogenated alkyl group or an aryl group, R ³ is an alkyl group having 1 to ³ carbon atoms, an alkylene group or a cycloalkyl group, a is an integer of 0 or 1, b is 0, 1 Or an integer of 2.)   The metal oxide fine particles are oxidized of at least one metal element selected from titanium, iron, zinc, tungsten, tin, tantalum, zirconium, antimony, niobium, indium, cerium, silicon, aluminum, yttrium, lead and molybdenum. The method for producing a plastic lens according to claim 1, wherein the method is a fine product particle or a composite oxide fine particle.   The metal oxide fine particles are oxidized of at least one metal element selected from titanium, iron, zinc, tungsten, tin, tantalum, zirconium, antimony, niobium, indium, cerium, silicon, aluminum, yttrium, lead and molybdenum. Core-shell type metal in which the surface of a core particle composed of a fine particle or a complex oxide is coated with an oxide or complex oxide of at least one metal element selected from silicon, zirconium, antimony, tin and aluminum The method for producing a plastic lens according to claim 1, wherein the plastic lens is oxide fine particles.   The method for producing a plastic lens according to claim 1, wherein the polycarboxylic acid-based compound is a polycarboxylic acid or a polycarboxylic acid anhydride. The polycarboxylic acid-based compound represents the weight of the polycarboxylic acid-based compound as X, and the amount of the organosilicon compound (A) contained in the hard coat layer film-forming coating composition on the basis of SiO ₂ conversion. When the obtained weight is represented by Y, it is contained in the hard coat layer film-forming coating composition in such a ratio that the weight ratio (X / Y) is 5/100 to 45/100. The method for producing a plastic lens according to any one of claims 1 to 5.   The method for producing a plastic lens according to any one of claims 1 to 6, wherein the silica-based fine particles are hollow silica-based fine particles having an average particle diameter of 40 to 100 nm and having cavities therein. . Claim 1-7, wherein the irradiation of the far-infrared in step (4), the surface temperature of the multilayer coating film using a far-infrared ceramic heater and performing so that 70 to 130 ° C. The manufacturing method of the plastic lens of description. The method further includes a step (3a) of pre-curing the coating film by further heat-treating the coating film obtained in the step (3) under a temperature condition of 60 to 110 ° C. for 3 to 30 minutes. The manufacturing method of the plastic lens in any one of Claims 1-8 . It further includes a step (3b) of applying a water-repellent coating treatment coating composition containing a fluorine compound or a hydrolyzate thereof to the surface of the precured coating film obtained in the step (3a). The manufacturing method of the plastic lens of Claim 9 . The method for producing a plastic lens according to claim 10 , wherein the fluorine-based compound is a fluorosilane compound having a hydrolyzable group. 12. The plastic according to claim 1, further comprising a primer layer film containing an organic resin compound and metal oxide fine particles between the plastic lens substrate and the hard coat layer film. Lens manufacturing method. A plastic lens produced by the method according to claim 1, wherein a hard coat layer film and an antireflection layer film are formed on a plastic lens substrate. A plastic lens produced by the method according to claim 10 or 11, wherein a hard coat layer film, an antireflection layer film, and a water repellent coat layer film are formed on a plastic lens substrate. The plastic lens according to claim 13 or 14 , wherein a primer layer film is further provided between the plastic lens substrate and the hard coat layer film.