JPH11133204A - Plastic lens with hardened film - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the plastic lens for thin eye glasses free from interference fringes due to the difference in reflective index between the base lens and the film and superior in abrasion resistance and resistance to chemicals and the like by forming the film obtained by coating the surface of a specified sulfur- containing urethane type plastic lens with a specified coating composition and hardening it. SOLUTION: The surface of the sulfur-containing urethane type plastic lens obtained by reaction of an A component with a B component is coated with the coating composition composed essentially of a C component and the like and hardened to form the film. The A component is one or more kinds of polyisocyanate compounds and the B component is a polythiol containing a compound having >=4 mercapto groups represented by the formula in which each of R<1> -R<4> is selected from among -H, -CH2 SH, -CH2 S-CH2 CH2 SH, or the like. The C component is fine particles having a particle diameter of 1-300 μm comprising a composite oxide of Ti, Si, and Zr in a colloidal dispersion.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a plastic lens with a cured film. Furthermore, the present invention relates to a plastic lens provided with an antireflection film on a cured film.

[0002]

2. Description of the Related Art Synthetic resin lenses, especially diethylene glycol bis (allyl carbonate) resin lenses, are superior to glass lenses in safety, workability, fashionability, and the like.
Due to the development of hard coat technology and hard coat + anti-reflection technology, it has spread rapidly. However, the refractive index of diethylene glycol bis (allyl carbonate) resin is 1.
50, which is lower than that of a glass lens, the near vision lens has a disadvantage that the outer peripheral portion is thicker than the glass lens. For this reason, in the field of synthetic resin spectacle lenses,
Technology development for reducing the thickness by using a high refractive index resin material has been actively performed. Technical proposals therefor include JP-A-59-133211, JP-A-63-46213, JP-A-2-270859, and JP-A-7-25.
No. 2207 proposes a high refractive index resin material having a refractive index of 1.60 or more.

On the other hand, plastic eyeglass lenses have a disadvantage that they are easily scratched, so that a method of providing a silicon-based hard coat film on the surface of a plastic lens is generally used. However, when the same method is applied to a high-refractive-index plastic lens, interference fringes occur due to a difference in the refractive index between the plastic lens and the coating film, resulting in poor appearance. As technical proposals for solving this problem, Japanese Patent Publication No. Sho 61-54331 and Japanese Patent Publication No. Sho 63
No. 37142, a colloidal dispersion of silicon dioxide fine particles used in a silicon-based coating composition is made of Al, Ti, Zr, Sn, Sb having a high refractive index.
A coating technique has been disclosed, for example, in which a colloidal dispersion of inorganic oxide fine particles is used. JP-A-1-301517 discloses a method for producing a composite sol of titanium dioxide and cerium dioxide, and JP-A-2-264902 discloses a composite inorganic oxide fine particle of Ti and Ce; -68901 discloses Ti,
A technique is disclosed in which fine particles obtained by treating a composite inorganic oxide of Ce and Si with an organosilicon compound are used in a coating composition.

In Japanese Patent Application Laid-Open Nos. Hei 5-331304, Hei 6-11601 and Hei 9-5501, a high refractive index coating film is applied to the surface of a specific high refractive index plastic lens. It is disclosed to obtain a high-quality plastic lens.

[0005]

SUMMARY OF THE INVENTION Among the aforementioned prior arts,
JP-A-59-133211, JP-A-63-462
No. 13, JP-A-2-270859, JP-A-7-70885
The high-refractive index resin materials disclosed in Japanese Patent Application Laid-Open No.-252207 and the like alone were insufficient in terms of durability, such as surface hardness and abrasion resistance, required as plastic lenses for spectacles.

[0006] Further, regarding the above-mentioned coating technique, Japanese Patent Publication No. 61-54331 and Japanese Patent Publication No. 63-37
No. 142, Al, Sb
When inorganic oxide fine particles are used, the refractive index as a coating film is limited, and it is impossible to completely suppress interference fringes for a lens substrate having a refractive index of 1.60 or more. Further, when inorganic oxide fine particles of Zr and Sn were used, their dispersibility was unstable, and when used in large amounts, a transparent film could not be formed. Furthermore, since the oxide of Ti has extremely poor weather resistance, the coating formed from TiO ₂ has a problem in terms of durability.

[0007] Further, in the coating composition using composite fine particles of titanium dioxide and cerium dioxide disclosed in JP-A-2-264902 and JP-A-3-68901,
Cerium dioxide is used as a composite for improving the weather resistance of titanium dioxide, but the resulting coating is still insufficient in terms of weather resistance. Further, since cerium dioxide has a yellow tint, the cured coating obtained from these composite sols was somewhat yellowish.

[0008] The plastic lenses having a cured film described in JP-A-5-331304, JP-A-6-11601, and JP-A-9-5501 are particularly excellent in heat resistance, weather resistance, falling ball strength and the like. It was inferior.

Accordingly, the present invention has been made to solve these problems, and an object of the present invention is to eliminate interference fringes caused by a difference in refractive index between a base lens and a coating film, and further to provide abrasion resistance, chemical resistance, and resistance to chemicals. An object of the present invention is to provide a plastic lens for thin eyeglasses excellent in various durability such as warm water, heat resistance, weather resistance and falling ball strength.

[0010]

Means for Solving the Problems The inventors of the present invention have made intensive studies to achieve the above object, and as a result, have found that the surface of a sulfur-containing urethane-based plastic lens obtained by reacting the following components A and B can be used. It was found that the object of the present invention was achieved by providing a coating film obtained by applying and curing a coating composition containing the following components C and D as main components, and completed the present invention. .

A component. One or more polyiso (thio) cyanate compounds.

B component. A polythiol containing at least a compound having four or more mercapto groups represented by the following general formula [1].

[0013]

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C component. A colloidal dispersion of fine particles of (i) titanium, (ii) silicon and (iii) zirconium, which has a particle diameter of 1 to 300 mμ, is composed of a composite oxide.

D component. General formula _{^{R 5 R 6 a Si (OR}} 7) 1 or more hydrolysates of organosilicon compounds represented by the _3-a and / or partial condensate.

(Where R ⁵ is (A) a carbon number of 1 to 6
Hydrocarbon group, an organic group having (i) a vinyl group or (c) a methacryloxy group, a mercapto group, an amino group or an epoxy group, R ⁶ represents a hydrocarbon group having 1 to 4 carbon atoms, R ⁷ Represents a hydrocarbon group having 1 to 8 carbon atoms, an alkoxyalkyl group or an acyl group, and a represents 0 or 1. Hereinafter, the present invention will be described in more detail.

Examples of the polyiso (thio) cyanate compound which is the component A for forming the plastic lens substrate include tolylene diisocyanate, diphenylmethane diisocyanate, polymeric diphenylmethane diisocyanate, tolidine diisocyanate, naphthalenediisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, Xylylene diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane diisocyanate, tetramethyl xylylene diisocyanate, tolylene diisothiocyanate, diphenylmethane diisothiocyanate, tolidine diisothiocyanate, naphthalene diisothiocyanate, hexamethylene diisothiocyanate, isophorone diisonate Thiocyanate, xy Diisothiocyanate, 2.5
-Bis (isocyanatomethyl) bicyclo [2.2.
1] heptane, 2.6-bis (isocyanatomethyl)
Bicyclo [2.2.1] heptane, 3.8-bis (isocyanatomethyl) tricyclo [5.2.1,02,
6] -decane, 3.9-bis (isocyanatomethyl)
Tricyclo [5.2.02,6] -decane, 4.8
-Bis (isocyanatomethyl) tricyclo [5.2.
1.02,6] -decane, 4.9-bis (isocyanatomethyl) tricyclo [5.2.02,6] -decane, polyiso (thio) such as dimer acid diisocyanate
Cyanate compounds and allophanate-modified, burette-modified, and isocyanurate-modified compounds of these compounds can be mentioned, and they can be used alone or as a mixture of two or more as needed.

Specific examples of the compound having four or more mercapto groups represented by the general formula [1] of the component B include:
The following compounds are mentioned.

[0019]

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[0020]

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[0021]

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[0022]

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[0023]

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By reacting the compound having four or more mercapto groups with the component A, a compound having a high refractive index and a well-balanced durability such as falling ball strength, heat resistance, dyeability, and weather resistance can be obtained. A urethane sulfate-based plastic lens can be obtained. Further, as the B component, one or more polythiol compounds other than the general formula [1] can be used in combination. Specific examples thereof include di (2-mercaptoethyl) ether, 1,2-ethanedithiol, Butanedithiol, ethylene glycol dithioglycolate, trimethylolpropane tris (thioglycolate), pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetrakis (3
-Mercaptopropionate), 1,2-dimercaptobenzene, xylylenedithiol, 4-mercaptomethyl-3,6-dithio-1,8-octanedithiol. Further, a polyol compound can be used in combination as the B component. The amount of the compound having four or more mercapto groups represented by the general formula [1] in the component B is preferably used in the range of 5% by weight to 100% by weight. This is because if the amount is less than 5% by weight, a plastic lens with a cured film which is excellent in various endurance qualities aimed at by the present invention cannot be obtained.

The molding of the plastic lens is carried out by injecting a mixture of the polyisocyanate compound of the component A and the polythiol compound of the component B into a lens molding mold composed of a glass mold and a gasket or a tape, followed by heat polymerization. You. At this time, the use ratio of the polyisocyanate compound and the polythiol compound must be such that the NCO / SH (functional group) molar ratio is within a range of usually 0.5 to 3.0, preferably 0.5 to 1.5. is there. In addition, an internal release agent, a chain extender, a crosslinking agent, a light stabilizer, an ultraviolet absorber, an antioxidant,
Coloring agents such as disperse dyes, oil-soluble dyes and pigments, bluing agents, reaction catalysts, and the like can be appropriately added to the mixture of the A component and the B component.

Next, a coating composition for forming a cured film will be described. The component C is obtained by dispersing fine particles composed of a composite oxide of (i) titanium, (ii) silicon and (iii) zirconium in a water or organic solvent in a colloidal state. Specific examples of the dispersion medium include:
Water, hydrocarbons, esters, ketones, alcohols, cellosolves, amines, organic carboxylic acids and the like can be used. Further, these dispersion media can be used as a mixture of two or more kinds. In the composite oxide fine particles, at least a part of the composite oxide may be hydrated or hydroxylated.

The composite oxide fine particles used in the present invention preferably have a particle diameter of 1 to 300 μm. This is 300mμ
When the particle size exceeds 1 m, the obtained film tends to become cloudy and opaque. Conversely, when the particle size is less than 1 mμ, the hardness of the obtained film is insufficient, the scratch resistance and the abrasion resistance are poor, and the refractive index is further increased. There is a tendency that the rate cannot be increased sufficiently.

As the composite form, titanium oxide is used as the core of the fine particles, and the surface thereof is coated with zirconium oxide and silicon oxide (hereinafter referred to as composite oxide fine particles (C-1)) or titanium oxide. Compound oxide fine particles composed of silicon oxide or titanium, composite oxide fine particles composed of silicon and zirconium oxide are used as nuclei, and the surface of the fine particles is coated with at least one oxide of silicon oxide and zirconium oxide. Complex oxide fine particles (hereinafter referred to as composite oxide fine particles (C-2)) are preferred.

The component (C-1) is described in detail below, and stable weather resistance can be secured in the case of such a composite form.

The refractive index of titanium oxide shows a value in the range of 2.2 to 2.7 depending on the crystal structure, and Al, Zr, Sn,
Higher than the refractive index of Sb oxide. However, the coating obtained by applying and curing a coating composition comprising a colloidal dispersion of titanium oxide and a silicon-based coupling agent as a main component has poor weather resistance and a decrease in adhesion between the substrate and the coating. And degradation of the film due to decomposition of vehicle components in the film.
This is considered to occur because titanium oxide absorbs and activates ultraviolet light of 230 to 320 nm. Therefore, activation of titanium oxide can be prevented by compounding titanium oxide and zirconium oxide. Further, the weather resistance of titanium oxide can be improved more than the composite of titanium oxide and cerium oxide. Furthermore, zirconium oxide has less coloring than cerium oxide and can make composite fine particles more colorless. In order to improve the weather resistance of titanium oxide in the two types of composite, the mixing ratio of titanium oxide and zirconium oxide is Z
rO ₂ / TiO ₂ (weight ratio) needs to be 0.05 or more. Further, when the zirconium oxide is too large, the refractive index is lowered. Therefore, the mixing ratio is preferably 10.0 or less. Further, by combining these two types with silicon oxide, it is possible to improve the hardness of the obtained film and the adhesion to the antireflection film. The mixing ratio of silicon oxide is preferably in the range of 5 to 80% by weight based on the total amount of the inorganic oxide. If the content is less than 5% by weight, the effect is insufficient, and if it is more than 80% by weight, the refractive index becomes considerably low.

The component (C-2) is described in detail below, and in such a composite form, stable weather resistance can be secured. As the composite form, fine particles having the following forms are preferable.

(1) Composite particles of titanium and silicon or titanium or silicon and zirconium, in which silicon atoms or silicon atoms and zirconium atoms are dissolved and uniformly dispersed in the crystal lattice of titanium oxide, are used as core particles. Composite oxide fine particles in which at least one oxide selected from silicon oxide and zirconium oxide is coated in one or more layers on the fine particles. Composite oxide fine particles (C-
The contents of titanium, silicon, and zirconium in 2) were determined by converting titanium, silicon, and zirconium to TiO ₂ and Si, respectively.
As a weight ratio in terms of O ₂ and ZrO ₂ , SiO ₂
/ TiO ₂ is 0.073 to 1.133, preferably 0.
09-0.400, ZrO ₂ / TiO ₂ 0.001
0.400, preferably 0.002 to 0.320. SiO ₂ / TiO ₂ of less than 0.073 and ZrO ₂ /
When TiO ₂ is less than 0.001, there is a possibility that a coating film having good weather resistance cannot be formed on the substrate from a coating solution containing the composite oxide fine particles (C-2), and conversely, SiO ₂ / Ti
In the case where O ₂ exceeds 1.133 and the case where ZrO ₂ / TiO ₂ exceeds 0.400, the refractive index of the composite oxide fine particles (C-2) becomes low, and thus the refractive index is sufficient. In order to obtain a high refractive index coating from a coating solution containing a composite oxide fine particle (C-2) which is not too high, a large amount of the composite oxide fine particle (C-2) is required, and a plastic lens with a high refractive index cured film is required. Can be economically disadvantageous.

The content of titanium, silicon and zirconium contained in the composite oxide core fine particles is determined by adding titanium, silicon and zirconium to TiO ₂ , SiO ₂ and Zr, respectively.
As a weight ratio in terms of O ₂ , SiO ₂ / TiO ₂
Is 0.053-0.429, and ZrO ₂ / TiO ₂ is 0.0
It is preferably from 01 to 0.300.

The above-mentioned composite oxide fine particles, including the composite oxide fine particles (C-1) and (C-2), have their surfaces treated with an organosilicon compound or an amine. preferable. When the surface of the composite oxide fine particles is modified by treatment with an organosilicon compound or an amine,
The dispersed state of the composite oxide fine particles in the coating liquid containing the composite oxide fine particles and the matrix such as the D component becomes stable for a long period of time. Further, the composite oxide fine particles whose surface is treated with an organosilicon compound or an amine has improved reactivity and affinity with a matrix such as D component,
As a result, the coating obtained from the coating liquid containing the composite oxide fine particles surface-treated with these has higher hardness, transparency, and scratch resistance than the coating obtained from the coating liquid containing the untreated composite oxide fine particles. Also excellent in nature. Further, the affinity between the composite oxide fine particles in the coating solution and the solvent is further improved as compared with the case where the composite oxide fine particles are not surface-treated.

The organosilicon compound used at this time has the formula: R ₃ SiX (R is an alkyl group, a phenyl group,
X represents an organic group having a vinyl group, a methacryloxy group, a mercapto group, an amino group, or an epoxy group, and X represents a hydrolyzable group. ), For example, trimethylsilane, dimethylphenylsilane, dimethylvinylsilane and the like. Alternatively, a bifunctional silane represented by R ₂ SiX ₂ , such as dimethylsilane, diphenylsilane, etc .; a trifunctional silane represented by RSix ₃ , such as methylsilane, phenylsilane, etc .; and a tetrafunctional silane represented by SiX ₄ Silanes, for example, tetraalkoxysilanes such as tetraethoxysilane. In the treatment, the hydrolyzable group may be untreated or hydrolyzed. Further, after the treatment, a state in which the hydrolyzable group has reacted with the —OH group of the fine particles is preferable, but there is no problem in stability even when a part remains.

Examples of the amine compound include ammonium or ethylamine, alkylamines such as triethylamine, isopropylamine and n-propylamine, aralkylamines such as benzylamine, alicyclic amines such as piperidine, monoethanolamine, triethanolamine and the like. Alkanolamines.

In order to modify the surface of the composite oxide fine particles with an organosilicon compound or an amine compound, for example, the composite oxide fine particles are mixed in an alcohol solution of these compounds,
After adding a predetermined amount of water and, if necessary, a catalyst, it is preferable to leave at room temperature for a predetermined time or to perform a heat treatment.

The surface of the composite oxide fine particles can also be modified by adding a hydrolyzate of these compounds and composite oxide fine particles to a mixed solution of water and alcohol and subjecting the mixture to heat treatment.

The amount of the organosilicon compound or amine compound used at this time is appropriately set according to the amount of hydroxyl groups present on the surfaces of the composite oxide fine particles.

The proportion of the composite oxide fine particles of the component C in the cured film is suitably from 10% by weight to 90% by weight, and it is necessary to adjust the coating composition so as to fall within this range. If the content is less than 10% by weight, the hardness of the cured film obtained is insufficient, and the refractive index of the film becomes low. If the content is 90% by weight or more, the adhesion between the substrate and the coating film is reduced, and the coating film after curing is cracked. Therefore, the use in the above range is preferable.

[0041] As the organic silicon compound formula is D component is represented by _{^{R 5 R 6 a Si (OR}} 7) 3-a, methyl trimethoxysilane, ethyl triethoxysilane, methyl triethoxysilane, phenyl tri Ethoxysilane, dimethyldimethoxysilane, phenylmethyldimethoxysilane,
Vinyltriethoxysilane, vinyltrimethoxysilane, vinyltris (β-methoxyethoxy) silane, γ
-Glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, γ-glycidoxypropylmethyldimethoxysilane, γ-glycidoxypropylmethyldiethoxysilane, β- (3.4-epoxycyclohexyl) Ethyltrimethoxysilane, γ-
Methacryloxypropyltrimethoxysilane, N-β
(Aminoethyl) γ-aminopropyltrimethoxysilane, N-β (aminoethyl) γ-aminopropylmethyldimethoxysilane, γ-aminopropyltriethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, γ-mercapto And propyltrimethoxysilane. These may be used alone or as a mixture of two or more. In addition, it is preferable that these are hydrolyzed in the absence of a solvent or in an organic solvent such as an alcohol in the presence of an acid. Further, the mixture may be mixed with the colloidal dispersion of composite oxide fine particles after hydrolysis, or may be mixed with the colloidal dispersion of composite oxide fine particles and then hydrolyzed. The proportion of the film component derived from the hydrolyzate of the organosilicon compound of the component D in the cured film is suitably from 10% by weight to 90% by weight. If the content is 10% by weight or less, the adhesion between the substrate and the coating film is reduced, and if it is 90% by weight or more, the adhesion of the antireflection film composed of an inorganic substance is reduced. The preparation of the coating composition is preferred.

The coating composition according to claim 1 comprises the above-mentioned components C and D as main components, and further has the following component E for the purpose of improving the performance of the coating solution and imparting functionality to the cured film. If necessary, one or more components selected from J components can be added.

The organosilicon compound represented by the general formula Si (OR ⁸ ) _{4 as the} component E can easily adjust the refractive index of the formed film while maintaining the transparency of the film, and further apply a coating solution. It is used for the purpose of accelerating the curing speed of a later film. By using the E component, the refractive index of the cured film can be appropriately changed according to the refractive index of the base lens, and even if the content of the composite oxide fine particles is reduced, the adhesion of the antireflection film is reduced. It is possible to get. Further, by using the tetrafunctional organosilicon compound represented by the E component as a coating composition, the curing speed at the time of forming a cured film is increased, and in particular, a base such as a sulfur-containing urethane-based lens from which a dye is easily removed from a fabric lens. When a film is formed on a material, the amount of the loss can be suppressed, and the change in color tone of the dyed lens before and after the film is formed can be reduced. Examples of the tetrafunctional silane compound include tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, tetraisopropoxysilane, tetrabutoxysilane, tetraphenoxysilane, tetraacetoxysilane, tetraallyloxysilane, tetrakis (2-methoxyethoxy) silane ,
Examples include tetrakis (2-ethylbutoxy) silane and tetrakis (2-ethylhexyloxy) silane. These may be used alone or as a mixture of two or more. In addition, it is preferable that these are hydrolyzed in the absence of a solvent or in an organic solvent such as an alcohol in the presence of an acid. The proportion of the coating component derived from the hydrolyzate of the tetrafunctional organosilicon compound of component E in the cured coating is preferably from 0% by weight to 50% by weight. This is 50
When the content is more than the weight%, cracks easily occur in the cured film.

F, Si, Al, Sn, Sb, T
a, at least one of colloidal dispersions of fine particles composed of oxides of elements selected from the group consisting of a, Ce, La, Fe, Zn, W, Zr and In and / or Si, Al, S
n, Sb, Ta, Ce, La, Fe, Zn, W, Zr,
A colloidal dispersion of fine particles composed of a composite oxide of two or more elements selected from the group consisting of In and Ti (excluding fine particles composed of a composite oxide of Ti, Zr and Si). One or more types are used to optimize the refractive index, adhesion, dyeability, heat resistance, and the like of the obtained coating film depending on the type of the base lens. These are specifically S
iO ₂ , Al ₂ O ₃ , SnO ₂ , Sb ₂ O ₅ , Ta ₂ O ₅ , CeO ₂ ,
Inorganic oxide fine particles such as La ₂ O ₃ , Fe ₂ O ₃ , ZnO, WO ₃ , ZrO ₂ , and In ₂ O ₃ are colloidally dispersed in water or an organic solvent. Alternatively, composite fine particles composed of two or more of these inorganic oxides are colloidally dispersed in water or an organic solvent. Examples of these composite oxides include titanium, cerium and silica composite oxides,
Examples include a composite oxide of titanium, iron and silica, a composite oxide of tin and tungsten, a composite oxide of tin and zinc, and a composite oxide of tin, titanium and zirconium. In any case, the particle diameter is preferably about 1 to 300 μm, and the kind applied to the coating composition of the present invention and the amount to be used are determined by the target film performance. Further, in order to enhance the dispersion stability in the coating liquid, it is also possible to use those obtained by treating the surface of fine particles with an organosilicon compound or an amine compound in the same manner as for the component C.

One or more components selected from the group consisting of polyfunctional epoxy compounds, polyhydric alcohols, polycarboxylic acids and polycarboxylic anhydrides, which are the G components, improve the dyeability of the coating film formed, or Used for the purpose of improving various durability. Polyfunctional epoxy compounds include (poly)
Ethylene glycol, (poly) propylene glycol,
Examples include diglycidyl ethers of difunctional alcohols such as neopentyl glycol, catechol, resorcinol, and alkylene glycol, and di- or triglycidyl ethers of trifunctional alcohols such as glycerin and trimethylolpropane. Polyhydric alcohols include (poly) ethylene glycol, (poly) propylene glycol, neopentyl glycol, catechol,
Examples include bifunctional alcohols such as resorcinol and alkylene glycol, or trifunctional alcohols such as glycerin and trimethylolpropane, and polyvinyl alcohol. Examples of the polycarboxylic acid include malonic acid, succinic acid, adipic acid, azelaic acid, maleic acid, orthophthalic acid, terephthalic acid, fumaric acid, itaconic acid, and oxaloacetic acid. Examples of the polycarboxylic anhydride include succinic anhydride, maleic anhydride, itaconic anhydride, 1.2-dimethylmaleic anhydride, phthalic anhydride, hexahydrophthalic anhydride, and naphthalic anhydride. The proportion of the coating component derived from the component E in the cured coating is from 0% by weight to 4%.
0% by weight is suitable. This is because if the content is 40% by weight or more, the adhesion between the cured film and the antireflection film made of an inorganic substance provided thereon is reduced.

The hindered amine compound of the H component is used for the purpose of improving the dyeability of the formed film. For example, bis (2,2,6,6, -tetramethyl-4-piperidyl) sebacate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, 1- [2-
[3- (3,5-Di-t-butyl-4-hydroxyphenyl) propionyloxy] ethyl] -4- [3-
(3,5-di-t-butyl-4-hydroxyphenyl)
Propionyloxy] -2,2,6,6-tetramethylpiperidine, 8-benzyl-7,7,9,9, -tetramethyl-3-octyl-1,3,8, -triazaspiro [4,5] Undecane-2,4-dione, 4-benzoyloxy-2,2,6,6-tetramethylpiperidine, 8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8 -Triazaspiro [4.5] decane-2,4-dione, dimethyl succinate 1- (2-
(Hydroxyethyl) -4-hydroxy-2,2,6,6
-Tetramethylpiperidine polycondensate, poly [[6-
(1,1,3,3-tetramethylbutyl) amino-1,
3,5-triazine-2,4-diyl] [(2,2,2
6,6-tetramethyl-4-piperidyl) imino] hexamethylene [(2,2,6,6-tetramethyl-4-
Piperidyl) imino]], N, N'-bis (3-aminopropyl) ethylenediamine-2,4-bis [N-butyl-N- (1,2,2,6,6-pentamethyl-4piperidyl) amino] -6-chloro-1,3,5-triazine condensate, bis (1,2- (3,5-di-t-butyl-4-hydroxybenzyl) -2-n-butylmalonate
2,2,6,6-pentamethyl-4-piperidyl) and the like. The upper limit of the amount used is desirably 3% by weight or less based on the solid content of the coating liquid. If the amount is more than 3% by weight, the hardness of the cured film, warm water resistance, etc. are undesirably reduced.

Component I is selected from the group consisting of amines, amino acids, metal acetylacetonates, metal salts of organic acids, perchloric acids or salts thereof, acids and metal chlorides.
More than one species is a curing catalyst used to promote the curing of silanol or epoxy groups. The use of these curing catalysts makes it possible to accelerate the film formation reaction. Specific examples thereof include amines such as n-butylamine, triethylamine, guanidine and biguanide; amino acids such as glycine; metal acetyls such as aluminum acetylacetonate, chromium acetylacetonate, titanyl acetylacetonate, and cobalt acetylacetonate. Acetonate, sodium acetate, zinc naphthenate, cobalt naphthenate, zinc octylate,
Metal salts of organic acids such as tin octylate, perchloric acids such as perchloric acid, ammonium perchlorate and magnesium perchlorate or salts thereof, acids such as hydrochloric acid, phosphoric acid, nitric acid, paratoluenesulfonic acid, or SnCl ₂ , AlCl ₃ , FeC
Metal chlorides that are Lewis acids such as l ₃ , TiCl ₄ , ZnCl ₂ , and SbCl ₃ can be used. These curing catalysts of the component I can be used by adjusting the type and amount of use according to the composition of the coating liquid and the like. The upper limit of the amount used is desirably 5% or less based on the solid content of the coating liquid. If the amount is more than 5%, the hardness of the cured film, the warm water resistance and the like are undesirably reduced.

The J component is an organosilicon compound represented by the following general formula [2].

[0049]

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(Where R ⁹ and R ¹⁰ represent a hydrocarbon group having 1 to 6 carbon atoms, R ¹¹ and R ¹² represent a hydrocarbon group or alkoxyalkyl group having 1 to 8 carbon atoms, and A represents a carbonate group or an epoxy group) Represents an organic group having a group, and b and c represent 0
Or represents 1. Here, specific examples of the organic group having a carbonate group or an epoxy group of A include the following.

[0051]

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[0052]

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[0053]

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[0054]

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[0055]

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[0056]

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[0057]

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[0058]

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[0059]

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[0060]

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The use of the J component can reduce or improve bumps and pinholes in the coating film. Generally, the coating operation on a plastic lens or the like is performed in a dustproof environment. However, if the dustproof degree is insufficient, the yield decreases. For this reason, the coating composition of the present invention is particularly effective in improving the yield under such an environment. When the H component is used, it is preferable to use it after hydrolysis in the absence of a solvent or in an organic solvent such as an alcohol in the presence of an acid. The proportion of the coating component derived from the hydrolyzate of the organosilicon compound as the component J in the cured coating is suitably from 3% by weight to 50% by weight. When the content is less than 3% by weight, the effect of improving the yield is insufficient, and when the content is more than 50% by weight, the abrasion resistance is reduced. Therefore, it is preferable to prepare the coating composition within this range.

The coating composition used in the present invention comprises:
A general organic solvent can be used for adjusting the solid content concentration and adjusting the liquid properties such as surface tension, viscosity, and evaporation speed. Specifically, solvents such as alcohols, ketones, cellosolves, and carboxylic acids are used alone or as a mixture.

The coating composition of the present invention may contain a small amount of a surfactant, an antistatic agent, an ultraviolet absorber, an antioxidant, a disperse dye, an oil-soluble dye,
Addition of a fluorescent dye / pigment, a photochromic compound or the like can also improve the applicability of the coating solution and the film performance after curing.

Further, in applying the coating composition of the present invention, the surface of the substrate is treated in advance with an alkali treatment, an acid treatment, a surfactant treatment, an inorganic or organic material, in order to improve the adhesion between the substrate lens and the film. It is effective to perform a polishing treatment, a primer treatment or a plasma treatment with fine particles.

As a coating / curing method, a coating is formed by applying a coating liquid by a dipping method, a spinner method, a spray method or a flow method and then drying by heating at a temperature of 40 to 200 ° C. for several hours. be able to. The thickness of the cured film is preferably from 0.5 to 30 μm. If the thickness is less than 0.5 μm, the resulting coating is not sufficiently abrasion-resistant, and if it exceeds 30 μm, cracks tend to occur in the coating.

As described above, the coating obtained by applying and curing the coating composition containing the components C and D on the surface of the sulfur-containing urethane-based plastic lens obtained by reacting the components A and B. By providing
There is no interference fringe due to the difference in the refractive index between the base lens and the coating, and a plastic lens for thin eyeglasses with excellent durability such as abrasion resistance, chemical resistance, warm water resistance, heat resistance, weather resistance, falling ball strength, etc. Obtainable. In addition, by adding one or more components selected from the components E to J to the coating composition, the performance of the coating composition and the resulting cured film can be improved.

Further, by providing a single-layer or multi-layer anti-reflection film made of an inorganic material on the above-mentioned plastic lens with a cured film, it is possible to reduce reflection and improve transmittance, thereby improving the function as a spectacle lens. Can be improved. As the inorganic substance, SiO, SiO ₂ , Si
₃ N _4, with a _{TiO 2, ZrO 2, Al 2} O 3, MgF 2, Ta 2 O 5 or the like, it is possible to form the anti-reflection film by a thin film formation method such as a vacuum deposition method.

[0068]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples.

Example 1 (1) Preparation of Plastic Lens Substrate 103 g of m-xylylene diisocyanate and a tetrafunctional mercapto compound represented by the following structural formula (A component, B component,
The mixing ratio of the component C is a molar ratio, A / B / C = 80/10 /
10)

[0070]

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100 g, dibutyltin dilaurate 0.1 g
02 g, internal mold release agent 0.15 g, 2- (5-methyl-2)
-Hydroxyphenyl) benzotriazole 0.09 g
Are mixed and thoroughly stirred, and then mixed under vacuum of 5 mmHg.
Degassing was performed for 0 minutes. Thereafter, the mixture is poured into a mold composed of a glass mold and a tape, kept at 40 ° C. for 7 hours, and then polymerized in a heating furnace in which the temperature is raised from 40 ° C. to 120 ° C. over 10 hours. The tape was removed to obtain a sulfur-containing urethane resin lens. The obtained lens had a refractive index of 1.66 and an Abbe number of 32.

(2) Preparation of coating composition In a flask equipped with a stirrer, 12.43 g of γ-glycidoxypropyltrimethoxysilane was added, and then 3.41 g of 0.05N hydrochloric acid was added and stirred for 30 minutes. did. Subsequently, 28.30 g of distilled water and a silicon-based surfactant (trade name “L-7604” manufactured by Nippon Unicar Co., Ltd.)
0.04 g, and a methanol-dispersed titanium dioxide-zirconium dioxide-silicon dioxide composite fine particle sol (Ti
O ₂ / ZrO ₂ / SiO ₂ = 68/17/15 (weight ratio), solid content concentration 20.5% by weight, a solid solution of TiO ₂ and SiO ₂ as a nucleus, and a nucleus of a solid solution of ZrO ₂ and SiO ₂ 55.85 g of the three-layered composite oxide particles coated and further coated with SiO ₂ ) were added in this order, and the mixture was sufficiently stirred. The mixture was allowed to stand at 0 ° C. for 24 hours for aging to obtain a coating composition.

(3) Formation of Cured Coating The sulfur-containing urethane-based resin lens produced by the above method was immersed in a 5% by weight aqueous solution of sodium hydroxide for 5 minutes, washed and dried, and adjusted in (2). Using a coating solution, coating was performed by a spin coating method. The spin-coating conditions were as follows: after applying the hard coat liquid during low rotation, spin-off was performed at a rotation speed of 2500 rpm and a rotation time of 1 second. After the application, the coating was temporarily baked at 120 ° C. for 30 minutes, cooled, applied to the remaining surface under the same conditions, and heated and cured at 120 ° C. for 3 hours to form a cured film. The thickness of the obtained film was 2.3 μm.

(4) Formation of Antireflection Film After the lens having the cured film formed by the above method is exposed to argon gas plasma of 200 W in vacuum for 30 seconds, the lens is formed from the lens side by vacuum evaporation. Five thin films of SiO ₂ , ZrO ₂ , SiO ₂ , ZrO ₂ , and SiO ₂ were formed toward the atmosphere. The optical film thickness of the formed anti-reflection film is about λ / 4 for SiO ₂ in order, and ZrO ₂ and SiO
₂ is about λ / 4, the next ZrO ₂ is about λ / 4, and the uppermost SiO ₂ is about λ / 4 (design wavelength λ is 5
10 nm).

The following performance evaluation tests were performed on the synthetic resin lenses obtained as described above, and the results are shown in Table 1. Appearance: The presence or absence of coloring of an unstained lens (white lens) was visually evaluated. Transmittance: The average transmittance of visible light of an unstained lens (white lens) was measured with a spectrophotometer. Interference fringes: Regarding the presence or absence of the occurrence of interference fringes, the light of a fluorescent lamp was reflected on the lens surface in a state where the background was blackened, and the occurrence of a rainbow pattern due to light interference was visually observed. The judgment was made as follows. ：: No rainbow pattern is observed. Δ: A slight rainbow pattern is observed. ×: A rainbow pattern is clearly observed. Scratch resistance: Load 1k with # 0000 steel wool
The state of the film after 10 reciprocations at g / cm ² was observed. A: Almost no damage. B: Slightly scratched. C: Many scratches are made. Adhesion: After immersion in hot water at 70 ° C for 2 hours, 11 parallel line-shaped scratches were made on the lens surface with a knife at 1 mm intervals vertically and horizontally each to make 100 squares, and after adhering and peeling cellophane tape, The number of squares remaining without peeling off the film was checked. Weather resistance: After exposure for 150 hours using a xenon long life fade meter (manufactured by Suga Test Instruments Co., Ltd.), the following evaluation was performed. i) Appearance: The presence or absence of coloring of an unstained lens (white lens) was visually evaluated. ii) Transmittance: After the test, the average transmittance of visible light of the unstained lens (white lens) was measured with a spectrophotometer. iii) Adhesion: A cross-cut tape test similar to that described above was performed on the exposed surface of the lens after the test.

Heat resistance The lens framed in a metal frame was placed in a constant temperature bath at 80 ° C. for 30 minutes and cooled to room temperature, and the degree of film cracking was examined. A: Almost no film crack. B: There are some film cracks. C: There are many film cracks.

(Example 2) (1) Preparation of plastic lens substrate Tetrathiol compound 45.81 represented by the following structural formula
g,

[0078]

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A mixture of 27.66 g of 4-mercaptomethyl-3,6-dithio-1,8-octanedithiol and 100 g of m-xylylene diisocyanate, 0.02 g of dibutyltin dilaurate, 0.15 g of an internal mold release agent,
After mixing 0.09 g of-(5-methyl-2-hydroxyphenyl) benzotriazole and stirring sufficiently, 5 m
Degassed for 60 minutes under mHg vacuum. Then, it is poured into a mold composed of a glass mold and a gasket,
After that, polymerization was carried out in a heating furnace in which the temperature was raised from 40 ° C. to 120 ° C. over 10 hours. After cooling, the glass mold and the gasket were removed to obtain a sulfur-containing urethane resin lens. The obtained lens had a refractive index of 1.66 and an Abbe number of 3.
It was 2.

(2) Preparation of coating composition Ethyl cellosolve 4 was placed in a flask equipped with a stirrer.
1.15 g, γ-glycidoxypropyltrimethoxysilane 38.44 g, and tetramethoxysilane 4.13 g were added in this order with stirring.
90 g was added and stirred for 30 minutes. Subsequently, a silicon-based surfactant (trade name “L-760” manufactured by Nippon Unicar Co., Ltd.)
4 ") and 0.04g further methyl cellosolve dispersed titanium dioxide - zirconium dioxide - silicon composite fine particle sol dioxide _{(TiO 2 / ZrO 2 / SiO} 2 = 68/17/15
(Weight ratio), solids concentration 20.5% by weight, TiO ₂ and Z
103.39 g of a composite oxide fine particle having a core of a solid solution of rO ₂ and SiO ₂ and the nucleus coated with SiO ₂ ) was added thereto, stirred sufficiently, left to stand at 0 ° C. for 24 hours and aged to obtain a coating composition. Was.

(3) Formation of Cured Film A cured film was formed on the above-mentioned sulfur-containing urethane resin lens substrate by applying and curing in the same manner as in Example 1 using the coating composition prepared by the above method. In addition, the film thickness of the obtained film is
It was 2.1 μm.

(4) Formation of Antireflection Film An antireflection film was formed on the lens having the cured film formed by the above method in the same manner as in Example 1. A performance evaluation test similar to that of Example 1 was performed on the synthetic resin lens obtained as described above, and the results are shown in Table 1.

Example 3 (1) Preparation of Plastic Lens Base Material Tetrathiol compound 65.12 represented by the following structural formula
g,

[0084]

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To a mixture of 18.4 g of 4-mercaptomethyl-3,6-dithio-1,8-octanedithiol, 100 g of m-xylylene diisocyanate, 0.02 g of dibutyltin dilaurate, 0.15 g of an internal mold release agent,
After mixing 0.09 g of-(5-methyl-2-hydroxyphenyl) benzotriazole and stirring sufficiently, 5 m
Degassed for 60 minutes under mHg vacuum. Then, it is poured into a mold composed of a glass mold and a gasket,
After that, polymerization was carried out in a heating furnace in which the temperature was raised from 40 ° C. to 120 ° C. over 10 hours. After cooling, the glass mold and the gasket were removed to obtain a sulfur-containing urethane resin lens. The obtained lens had a refractive index of 1.66 and an Abbe number of 3.
It was 2.

(2) Preparation of Coating Composition Methyl cellosolve 6 was placed in a flask equipped with a stirrer.
8.18 g, 13.12 g of γ-glycidoxypropyltrimethoxysilane, 27.58 g of γ-glycidoxypropylmethyldiethoxysilane, tetramethoxysilane 1
6.91 g were added in order with stirring, and then 18.02 g of 0.05 N hydrochloric acid was added and stirred for 30 minutes. continue,
Methanol dispersion of titanium dioxide - zirconium dioxide - silicon composite fine particle sol dioxide (TiO ₂ / ZrO ₂ / SiO
₂ = 64/16/20 (weight ratio), solid content concentration 30% by weight, a solid solution of TiO ₂ and SiO ₂ as a core
and rO ₂ and the surface of a composite particle having a coated fine particle structure of SiO ₂ solid solution is treated with dimethoxy diphenyl silane) 75.05G and glycerin diglycidyl ether (Nagase & Co., Ltd., trade name "Denacol EX
-313 ") 5.67 g, and 0.04 g of a silicon surfactant (trade name" L-7001 "manufactured by Nippon Unicar Co., Ltd.).
4g, magnesium perchlorate 0.471 as curing catalyst
After adding 3 g in this order and sufficiently stirring, the mixture was left to stand at 0 ° C. for 24 hours for aging to obtain a coating composition.

(3) Formation of a cured film The coating composition prepared by the above method was applied to the sulfur-containing urethane-based resin lens substrate by a dipping method at a pulling rate of 15 cm / min. After application,
The composition was cured at 120 ° C. for 3 hours to form a cured film. In addition, the film thickness of the obtained film was 2.1 μm. The cured plastic film-coated plastic lens was cured by using a commercially available plastic lens dye (Seiko Plux Amber D).
When dyeing was carried out in a dyeing bath at a temperature of 3 ° C. for 3 minutes, the total light transmittance was 58%, indicating good dyeability.

(4) Formation of Antireflection Film An antireflection film was formed on the lens having the cured film formed by the above method in the same manner as in Example 1. A performance evaluation test similar to that of Example 1 was performed on the synthetic resin lens obtained as described above, and the results are shown in Table 1.

Example 4 (1) Preparation of Plastic Lens Substrate Tetrathiol compound 56.18 represented by the following structural formula
g,

[0090]

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A mixture of 23.05 g of 4-mercaptomethyl-3,6-dithio-1,8-octanedithiol and 100 g of m-xylylene diisocyanate, 0.02 g of dibutyltin dilaurate, 0.15 g of an internal mold release agent,
After mixing 0.09 g of-(5-methyl-2-hydroxyphenyl) benzotriazole and stirring sufficiently, 5 m
Degassed for 60 minutes under mHg vacuum. Thereafter, the mixture is poured into a mold composed of a glass mold and a tape.
The polymerization was carried out in a heating furnace in which the temperature was raised from 40 ° C. to 120 ° C. over 10 hours, and after cooling, the glass mold and the tape were removed to obtain a sulfur-containing urethane resin lens. The obtained lens had a refractive index of 1.66 and an Abbe number of 32.

(2) Preparation of Coating Composition Bis (2,2,6,6) was added to the coating composition prepared in the same manner as in Example 3 as a hindered amine compound.
0.1 g of 6-tetramethyl-4-piperidyl) sebacate (trade name: SANOL LS-770, manufactured by Sankyo Co., Ltd.) was added, and ripening was performed in the same manner.

(3) Formation of Cured Film A cured film was formed on the above-mentioned sulfur-containing urethane resin lens substrate by applying and curing in the same manner as in Example 3 using the coating composition prepared by the above method. In addition, the film thickness of the obtained film is
It was 2.5 μm. When this lens was stained with the same dye as in Example 3, the total light transmittance was 4%.
2%, showing better dyeability than Example 3.

(4) Formation of Antireflection Film An antireflection film was formed on the lens having the cured film formed by the above method in the same manner as in Example 1. A performance evaluation test similar to that of Example 1 was performed on the synthetic resin lens obtained as described above, and the results are shown in Table 1.

Example 5 (1) Preparation of Coating Composition Methyl cellosolve 6 was placed in a flask equipped with a stirrer.
8.18 g, 13.12 g of γ-glycidoxypropyltrimethoxysilane and 27.58 g of γ-glycidoxypropylmethyldiethoxysilane are added in order with stirring, and then 8.41 g of 0.05N hydrochloric acid water is added. Stir for 30 minutes. Subsequently, 50.05 g of the same methanol-dispersed titanium dioxide-zirconium dioxide-silicon dioxide composite fine particle sol used in Example 3 and a methanol-dispersed tin oxide-tungsten oxide composite fine particle sol (solid content: 30% by weight, treated with triethylamine) 27.68 g, a silicon-based surfactant (trade name “L-
7001 ″) was added in this order, and the mixture was sufficiently stirred. The mixture was allowed to stand at 0 ° C. for 24 hours for aging to obtain a coating composition.

(2) Formation of a cured film The same sulfur-containing urethane resin lens base material as obtained in Example 1 was immersed in a 5% by weight aqueous solution of sodium hydroxide for 5 minutes, washed and dried, and then dried. Using the coating liquid prepared in (1), application was performed by a dipping method at a pulling rate of 12 cm / min. After application, the coating was cured at 120 ° C. for 3 hours to form a cured coating. In addition, the film thickness of the obtained film was 2.2 μm.

(3) Formation of Antireflection Film An antireflection film was formed on the lens having the cured film formed by the above method in the same manner as in Example 1. A performance evaluation test similar to that of Example 1 was performed on the synthetic resin lens obtained as described above, and the results are shown in Table 1.

Example 6 (1) Preparation of Coating Composition Methyl cellosolve 9 was placed in a flask equipped with a stirrer.
2.94 g, 20.55 g of γ-glycidoxypropyltrimethoxysilane, an organosilicon compound represented by the following structural formula

[0099]

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14.28 g were added in sequence with stirring, and then 8.65 g of 0.05N hydrochloric acid was added and stirred for 30 minutes. Subsequently, 63.98 g of the same methanol-dispersed titanium dioxide-zirconium dioxide-silicon dioxide composite fine particle sol used in Example 1 and glycerin diglycidyl ether (trade name "Denacol EX" manufactured by Nagase & Co., Ltd.)
-313 ") 10.66 g, silicone surfactant (trade name" L-7001 ", manufactured by Nippon Unicar Co., Ltd.) 0.0
After adding 4 g and 0.75 g of aluminum acetylacetonate as a curing catalyst in this order and sufficiently stirring, the mixture was left to stand at 0 ° C. for 24 hours for aging to obtain a coating composition.

(2) Formation of cured film The same sulfur-containing urethane resin lens substrate as obtained in Example 1 was immersed in a 5% by weight aqueous sodium hydroxide solution for 5 minutes, washed and dried, and then dried. Using the coating liquid prepared in (1), coating was performed by a dipping method at a pulling rate of 15 cm / min. After application, the coating was cured at 120 ° C. for 3 hours to form a cured coating. In addition, the film thickness of the obtained film was 2.3 μm. Note that this lens was used in Example 3.
When dyeing was carried out using the same dyeing agent as in the above, the total light transmittance was 49% and good dyeing properties were exhibited.

(3) Formation of Antireflection Film An antireflection film was formed on the lens having the cured film formed by the above method in the same manner as in Example 1. A performance evaluation test similar to that of Example 1 was performed on the synthetic resin lens obtained as described above, and the results are shown in Table 1.

Comparative Example 1 (1) Preparation of Plastic Lens Substrate 87 g of 4-mercaptomethyl-3,6-dithio-1,8-octanedithiol, 94 g of m-xylylenediisocyanate, 0.02 g of dibutyltin dilaurate, internal After 0.15 g of a release agent and 0.09 g of 2- (5-methyl-2-hydroxyphenyl) benzotriazole were mixed and sufficiently stirred, deaeration was performed under a vacuum of 5 mmHg for 60 minutes. Thereafter, the mixture is poured into a mold composed of a glass mold and a tape, and is maintained at 40 ° C. for 7 hours.
Polymerization was carried out in a heating furnace where the temperature was raised to 20 ° C. over 10 hours. After cooling, the glass mold and the tape were removed to obtain a sulfur-containing urethane resin lens. The obtained lens has a refractive index of 1.66,
Abbe number was 33.

(2) Formation of Cured Coating The sulfur-containing urethane-based resin lens produced by the above method was immersed in a 5% by weight aqueous solution of sodium hydroxide for 5 minutes, washed and dried, and adjusted in Example 1. Using the coating liquid, coating and curing were performed in the same manner as in Example 1.
In addition, the film thickness of the obtained film was 2.3 μm.

(3) Formation of antireflection film Example 1 was applied to a lens having a cured film formed by the above method.
An anti-reflection film was provided in the same manner as described above. A performance evaluation test similar to that of Example 1 was performed on the synthetic resin lens obtained as described above, and the results are shown in Table 1.

Comparative Example 2 (1) Preparation of Coating Composition Ethyl cellosolve 4 was placed in a flask equipped with a stirrer.
1.15 g, γ-glycidoxypropyltrimethoxysilane 38.44 g, and tetramethoxysilane 4.13 g were added in this order with stirring.
90 g was added and stirred for 30 minutes. Subsequently, 0.04 g of the same silicon-based surfactant used in Example 1 was further added, and methylcellosolve-dispersed titanium dioxide and cerium dioxide were added.
Silicon dioxide composite fine particle sol (TiO ₂ / CeO ₂ / SiO
₂ = 68/17/15 (weight ratio), solids concentration 20.5% by weight, tetramethoxysilane-treated product) 103.39 g), sufficiently stirred, left standing at 0 ° C. for 24 hours to ripen, and a coating composition was obtained. I got

(2) Formation of Cured Coating The same sulfur-containing urethane resin lens as prepared in Example 1 was immersed in a 5% by weight aqueous solution of sodium hydroxide for 5 minutes, washed and dried, and then dried. Using the coating liquid prepared in (1), coating was performed by a spin coating method. The application conditions and the curing conditions during spin coating were the same as in Example 1. The thickness of the obtained film was 2.2 μm.

(3) Formation of antireflection film Example 1 was applied to a lens having a cured film formed by the above method.
An anti-reflection film was provided in the same manner as described above. A performance evaluation test similar to that of Example 1 was performed on the synthetic resin lens obtained as described above, and the results are shown in Table 1.

[0109]

[Table 1]

[0110]

According to the present invention, it is possible to obtain a plastic lens with a cured film having an excellent appearance without interference fringes due to a difference in refractive index between the base lens and the coating. Further, it is possible to provide a thin spectacle plastic lens with a cured film which is particularly excellent in heat resistance and weather resistance as compared with a conventional thin plastic lens.

Claims (3)

[Claims] 1. A coating composition comprising the following components C and D as main components is applied and cured on the surface of a sulfur-containing urethane-based plastic lens obtained by reacting the following components A and B. A plastic lens with a cured film, characterized by having a coating. A component. One or more polyiso (thio) cyanate compounds. B component. The mercapto group represented by the following general formula [1]
A polythiol containing at least a compound having at least one compound. Embedded image C component. (I) titanium, (ii) silicon and (iii)
Particle diameter of composite oxide of zirconium is 1
Colloidal dispersion of fine particles of ~ 300 mμ. D component. General formula _{^{R 5 R 6 a Si (OR}} 7) 1 or more hydrolysates of organosilicon compounds represented by the _3-a and / or partial condensate. (Wherein, R ⁵ represents an organic group having (a) a hydrocarbon group having 1 to 6 carbon atoms, (b) vinyl group or (c) a methacryloxy group, a mercapto group, an amino group or an epoxy group, R ⁶ Represents a hydrocarbon group having 1 to 4 carbon atoms, R ⁷ represents a hydrocarbon group having 1 to 8 carbon atoms, an alkoxyalkyl group or an acyl group;
Or represents 1. ) 2. The plastic lens with a cured film according to claim 1, wherein the coating composition contains one or more components selected from the following components E to J. E component. At least one hydrolyzate and / or partial condensate of an organosilicon compound represented by the general formula: Si (OR ⁸ ) ₄ . (Where R ⁸ is 1 to 8 carbon atoms)
Represents a hydrocarbon group, an alkoxyalkyl group or an acyl group. ) F component. Si, Al, Sn, Sb, Ta, Ce, La,
One or more colloidal dispersions of fine particles composed of an oxide of an element selected from the group consisting of Fe, Zn, W, Zr and In and / or Si, Al, Sn, Sb, Ta,
Fine particles composed of a composite oxide of two or more elements selected from the group consisting of Ce, La, Fe, Zn, W, Zr, In and Ti (however, composed of a composite oxide of Ti, Zr and Si Or more of colloidal dispersions (excluding fine particles). G component. At least one selected from the group consisting of polyfunctional epoxy compounds, polyhydric alcohols, polycarboxylic acids and polycarboxylic anhydrides. H component. One or more selected from hindered amine compounds. I component. At least one selected from the group consisting of amines, amino acids, metal acetylacetonates, metal salts of organic acids, perchloric acids or salts thereof, acids and metal chlorides. J component. At least one hydrolyzate and / or partial condensate of an organosilicon compound represented by the following general formula [2]. Embedded image (Where R ⁹ and R ¹⁰ represent a hydrocarbon group having 1 to 6 carbon atoms, R ¹¹ and R ¹² represent a hydrocarbon group having 1 to 8 carbon atoms or an alkoxyalkyl group, and A has a carbonate group or an epoxy group. Represents an organic group, and b and c represent 0 or 1.) 3. A plastic lens with a cured film, wherein an antireflection film made of an inorganic substance is laminated on the plastic lens with the cured film according to claim 1.