JP2002131504A - Plastic lens having hard coating layer and its manufacturing method - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a plastic lens having a hard coating layer the productivity of which is increased and which has excellent wear resistance, abrasion resis tance and transparency, and its manufacturing method. SOLUTION: The hard coating layer being the hardened substance layer of a coating composition (A) containing polysilazane and multifunctional compound having two or more polymerizable functional groups having active energy beam hardenability is formed on the surface of the base material of the plastic lens.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a plastic lens having a hard coat layer having excellent abrasion resistance, scratch resistance and transparency on a lens surface, and a method for producing the same.

[0002]

2. Description of the Related Art In recent years, plastic lenses have been used as optical lens materials for eyeglasses and the like from the viewpoint of weight reduction and workability.

[0003] Since a plastic lens has a lower surface hardness than a glass lens and is easily damaged, formation of a hard coat layer on the lens surface is an essential condition for using a plastic lens.

Conventionally, an acrylic hard coat or a silicone hard coat has been used as a hard coat for a plastic lens or the like.

[0005] Acrylic hard coats are excellent in productivity but have insufficient abrasion resistance. Silicone hard coats are excellent in abrasion resistance but require a primer layer to enhance adhesion to a substrate. Since it is necessary to form a film and further requires a heating and firing step, a hard coat that has low productivity and can achieve both abrasion resistance and productivity has been required.

[0006]

SUMMARY OF THE INVENTION An object of the present invention is to provide a plastic lens having a hard coat layer which has high productivity and is excellent in abrasion resistance, scratch resistance and transparency, and a method for producing the same. I do.

[0007]

The present invention provides a plastic lens having a hard coat layer on at least one surface of a plastic lens substrate, wherein the hard coat layer comprises:
Provided is a plastic lens, which is a cured product layer of a coating composition (A) containing a polyfunctional compound having two or more active energy ray-curable polymerizable functional groups and polysilazane.

According to the present invention, the cured product layer of the coating composition (A) containing an active energy ray (especially ultraviolet ray) curable compound and polysilazane, such as abrasion resistance, scratch resistance and transparency. A plastic lens having a hard coat layer excellent in quality can be provided.

Further, the present invention provides a coating composition (A) containing a polyfunctional compound having two or more active energy ray-curable polymerizable functional groups and polysilazane on at least one surface of a plastic lens substrate. Forming a cured product layer of the coating composition (A) by applying and then curing the polyfunctional compound by irradiation with active energy rays and curing the polysilazane in any order or simultaneously. The present invention provides a method for producing a plastic lens characterized by the following.

According to the above invention, by using the coating composition (A) containing an active energy ray-curable compound and polysilazane, a hard coat layer can be directly formed on the surface of a plastic lens substrate, and Since the heat curing time can be shortened, a method for producing a plastic lens having the above-mentioned hard coat layer which is excellent in productivity can be provided.

[0011]

DESCRIPTION OF THE PREFERRED EMBODIMENTS In the following description, a polyfunctional compound having two or more active energy ray-curable polymerizable functional groups is simply referred to as a polyfunctional compound. Further, an acryloyl group and a methacryloyl group are collectively referred to as a (meth) acryloyl group, and the same applies to expressions such as a (meth) acryloyloxy group, (meth) acrylic acid, and (meth) acrylate.

The plastic lens of the present invention has a hard coat layer comprising a cured product of a coating composition (A) containing a polyfunctional compound and polysilazane on at least one surface of a plastic lens substrate. Note that, between the plastic lens substrate and the hard coat layer, a third layer made of another synthetic resin, for example, a layer of a thermoplastic resin such as a thermoplastic acrylic resin or an adhesive layer may be present. Good.

First, the plastic lens substrate will be described. Examples of the material of the plastic lens substrate used in the present invention include acrylic resin, diethylene glycol bisallyl carbonate resin (for example, CR39), polystyrene, aromatic polycarbonate resin, dimethacrylate having a nuclear halogen-substituted aromatic ring and 1 having an aromatic ring. Copolymer with functional monomer, copolymer with polyisocyanate and polythiol, methyl methacrylate / styrene resin, tricyclo methacrylate [5.2.1.
0 ^2,6 ] dec-8-yl / styrene resin, tricyclo [5.2.1.0 ^2,6 ] methacrylate / styrene / copolymer of crosslinkable polyfunctional monomer, containing aromatic ring Copolymer of di (meth) acrylate / aromatic ring-containing monomer / hydroxyl group-containing monomer, copolymer of aromatic ring-containing di (meth) acrylate / aromatic ring-containing monomer / epoxy group-containing monomer, Di (meth) acrylate containing a nucleus halogen-substituted aromatic ring and an alkylene glycol group / Aromatic ring-containing monomer /
A copolymer of a compound containing an aromatic ring and an epoxy group or a copolymer of styrene derivative / ethylene glycol dimethacrylate / specific diacrylate compound / specific epoxy-modified di (meth) acrylate is exemplified.

The plastic lens substrate can be obtained by molding the above-mentioned material into a predetermined shape by a method such as injection molding, casting or press molding. Note that CR
In the case of a substrate using a thermosetting resin such as 39, adhesion with the coating composition (A) can be improved by performing alkali cleaning in advance.

Next, the coating composition (A) will be described. Examples of the polyfunctional compound contained in the coating composition (A) include paragraph 001 of JP-A-11-268196.
Compounds described in 4-0019 and 0021-0043 are preferred.

Preferred polyfunctional compounds include compounds having two or more (preferably 2 to 50, more preferably 3 to 30) one or more polymerizable functional groups selected from (meth) acryloyl groups. No. Of these, a compound having two or more (meth) acryloyloxy groups, that is, a polyester of a compound having two or more hydroxyl groups such as a polyhydric alcohol and (meth) acrylic acid is preferable.

Compounds having various functional groups and bonds other than the polymerizable functional groups are also preferable. Particularly, a compound having a urethane bond (meth) acryloyl group (hereinafter referred to as acrylic urethane) and a compound having a urethane bond are preferable. (Meth) acrylic acid ester compounds which are not used are preferred.

The acrylic urethane includes the following compounds. 1) Acrylic urethane which is a reaction product of pentaerythritol or its polymer, polypentaerythritol, polyisocyanate and hydroxyalkyl (meth) acrylate, and has three active energy ray-curable polymerizable functional groups A polyfunctional compound having the above (more preferably 4 to 20). 2) acrylic urethane which is a reaction product of a hydroxyl group-containing poly (meth) acrylate of pentaerythritol or polypentaerythritol with polyisocyanate, and
A polyfunctional compound having three or more (more preferably 4 to 20) active energy ray-curable polymerizable functional groups.

Examples of the (meth) acrylate compound having no urethane bond include pentaerythritol poly (meth) acrylate and isocyanurate poly (meth) acrylate. The pentaerythritol-based poly (meth) acrylate is pentaerythritol or a polyester of polypentaerythritol and (meth) acrylic acid (preferably having 4 to 20 active energy ray-curable polymerizable functional groups). Say. Also, isocyanurate-based poly (meth)
The acrylate is a polyester of (meth) acrylic acid with an adduct obtained by adding 1 to 6 mol of caprolactone or alkylene oxide to 1 mol of tris (hydroxyalkyl) isocyanurate or tris (hydroxyalkyl) isocyanurate. It preferably has 2 to 3 active energy ray-curable polymerizable functional groups.)
Say.

In the present invention, a monofunctional compound having one polymerizable functional group which can be polymerized by an active energy ray (hereinafter, simply referred to as a monofunctional compound) is contained together with the preferred polyfunctional compound. Is also good.

As the monofunctional compound, a compound having a (meth) acryloyl group is preferable, and a compound having an acryloyl group is particularly preferable. In addition, other hydroxyl groups,
It may have a functional group such as an epoxy group. Preferred monofunctional compounds are (meth) acrylic acid esters, that is, (meth) acrylates. Specific examples include the compounds described in paragraph No. 0045 of JP-A-11-268196.

When a monofunctional compound is used, it is based on the total of the polyfunctional compound and the monofunctional compound (hereinafter, both compounds are collectively referred to as an active energy ray-curable component) in the coating composition (A). The proportion of monofunctional compound is
Although not particularly limited, it is preferably at most 60% by mass, particularly preferably at most 30% by mass. If the proportion of the monofunctional compound is too large, the cured product of the coating composition (A) will be too soft.

As the polysilazane contained in the coating composition (A), polysilazane (perhydropolysilazane) substantially free of an organic group, an alkyl group, an alkenyl group,
A hydrolyzable group such as an aryl group, a cycloalkyl group, or a polysilazane or an alkoxy group in which a hydrogen atom bonded to a carbon atom of these groups is partially or entirely substituted with a substituent is bonded to a silicon atom; And polysilazane in which an organic group such as an alkyl group is bonded to a nitrogen atom.

The silica formed from polysilazane is different from the silica formed from the hydrolyzable silane compound.
A denser silica is formed. For example, silica formed from perhydropolysilazane is denser than silica formed from a tetrafunctional hydrolyzable silane compound (eg, tetraalkoxysilane) and has excellent properties such as abrasion resistance.

When polysilazane has a hydrolyzable group at the silicon atom, it forms silica substantially free of organic groups by a hydrolysis reaction at the time of curing. In particular, perhydropolysilazane is preferred in view of its low firing temperature and denseness of a cured product after firing. A cured product obtained by sufficiently curing perhydropolysilazane becomes silica containing almost no nitrogen atoms.

In the case of polysilazane in which an organic group such as an alkyl group is bonded to a silicon atom, silica containing an organic group formed has a lower abrasion resistance and the like than silica formed from perhydropolysilazane. Although the properties may be poor, a tougher cured product can be obtained and the thickness can be increased, so that it may be preferable to perhydropolysilazane for some purposes.

These polysilazanes are composed of a polymer having a chain, cyclic or crosslinked structure, or a mixture having a plurality of these structures in the molecule. The average molecular weight of the polysilazane is preferably from 200 to 50,000. If the average molecular weight of the polysilazane is less than 200, it is difficult to obtain a uniform cured product even when calcined, and if it exceeds 50,000, it is difficult to dissolve in a solvent, and the coating composition (A) may become viscous, which is not preferable. .

The ratio of the polysilazane to the polyfunctional compound in the coating composition (A) can be appropriately selected depending on the abrasion resistance and the solubility. In particular, in consideration of the durability of adhesion to the substrate, 1 to 400 parts by mass of polysilazane is preferable based on 100 parts by mass of the polyfunctional compound. If the ratio of the polysilazane to the polyfunctional compound is less than 1 part by mass, sufficient abrasion resistance and scratch resistance cannot be obtained, and if it exceeds 400 parts by mass, the adhesion to the substrate tends to decrease.

The coating composition (A) may contain the following solvents or various functional additives in addition to the above basic components.

In the coating composition (A), a solvent is usually an essential component, and a solvent is used unless the active energy ray-curable component is a liquid having a particularly low viscosity.

As the solvent, a solvent in which both the active energy ray-curable component and the polysilazane are soluble is used. In addition, it is preferable to select and use an appropriate solvent depending on the type of the base material. In particular, when the storage stability of polysilazane is considered, a solvent containing no hydroxyl group in the molecule, for example, a hydrocarbon or a halogenated hydrocarbon , Ketones, ethers, esters and the like. Specifically, paragraph number 007 of JP-A-11-268196 is disclosed.
Solvents described in No. 4 are preferred. In the present invention, xylene or dibutyl ether is particularly preferred.

The amount of the solvent can be appropriately changed depending on conditions such as the required viscosity of the composition, the desired thickness of the cured product layer, and the drying temperature. In the present invention, the solvent is preferably used at a mass ratio of 100 times or less, preferably 0.1 to 50 times, to the active energy ray-curable component in the coating composition (A).

Functional compounding agents include high molecular weight compounds such as polymethyl methacrylate resin (PMMA), photopolymerization initiators, ultraviolet absorbers, light stabilizers, antioxidants, thermal polymerization inhibitors, leveling agents, Antifoaming agent, thickener, anti-settling agent, pigment (organic coloring pigment, inorganic pigment), coloring dye, infrared absorber, fluorescent whitening agent, antistatic agent, silane coupling agent, dispersant, curable catalyst ( And at least one functional compound selected from the group consisting of acids, alkalis, and salts. In order to improve the dyeability of the hard coat layer, di (meth) acrylate or tri (meth) acrylate having a molecular weight between crosslink points of 1,000 or more is also preferable.

The coating composition (A) preferably contains a photopolymerization initiator in order to efficiently cure the active energy ray-curable component. As the photopolymerization initiator, known photopolymerization initiators can be used, and commercially available photopolymerization initiators are particularly preferable. Examples of the photopolymerization initiator include arylketone photopolymerization initiators (for example, acetophenones, benzophenones, alkylaminobenzophenones, benzyls, benzoins, benzoin ethers, benzyldimethyl ketals, benzoylbenzoates, α-acylo) Oxime esters, etc.), sulfur-containing photopolymerization initiators (eg, sulfides, thioxanthones, etc.), acylphosphine oxide photopolymerization initiators (eg, acyldiarylphosphine oxide, etc.), diacylphosphine oxide photopolymerization initiators And other photopolymerization initiators. Specific examples include compounds described in paragraphs 0063 to 0065 of JP-A-11-268196. The photopolymerization initiator may be used in combination of a plurality of types,
It may be used in combination with a photosensitizer such as an amine.

The amount of the photopolymerization initiator used in the coating composition (A) is preferably from 0.01 to 20 parts by mass, more preferably from 0.1 to 1 part by mass, per 100 parts by mass of the active energy ray-curable component.
0 parts by mass is preferred.

Examples of the ultraviolet absorber include benzotriazole-based ultraviolet absorbers, benzophenone-based ultraviolet absorbers, salicylic acid-based ultraviolet absorbers, and phenyltriazine-based ultraviolet absorbers used as synthetic resin ultraviolet absorbers. When a benzotriazole-based, benzophenone-based, or salicylic acid-based ultraviolet absorber is used for the coating composition (A) containing polysilazane, the cured product of the coating composition (A) is easily colored when irradiated with active energy rays. For this reason, a phenyltriazine-based ultraviolet absorber having little coloring is particularly preferable. Specifically, 2-
[4-[(2-hydroxy-3-dodecyloxypropyl) oxy] -2-hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- [4 -[(2-hydroxy-3-tridecyloxypropyl) oxy] -2-hydroxyphenyl]
-4,6-bis (2,4-dimethylphenyl) -1,
3,5-triazine and the like are preferable from the viewpoint of solubility,
A phenyltriazine-based ultraviolet absorber containing a polymerizable functional group such as a (meth) acryloyl group in the molecule is also preferable from the viewpoint of preventing bleed-out.

In order to cure the polysilazane into silica, usually, heating called calcination is performed.
In the present invention, it is preferable to use a catalyst in order to lower the firing temperature of polysilazane. Depending on the type and amount of the catalyst, curing can be performed even at room temperature.

As the catalyst, it is preferable to use a catalyst which cures polysilazane at a lower temperature. Examples of such a catalyst include fine particles of a metal such as gold, silver, palladium, platinum and nickel described in JP-A-7-196886, and the above-mentioned metals described in JP-A-5-93275. Carboxylic acid complexes.

Further, instead of adding the catalyst to the coating composition (A), as described in JP-A-9-31333, a catalyst solution, specifically, an amine aqueous solution or the like is directly coated. The polysilazane can also be cured by contacting the composition (A) or exposing the composition to the vapor for a certain period of time.

JP-A-11-181290 describes that the curing of polysilazane is accelerated by irradiation with an active energy ray in the presence of a photoradical generator. By optimizing the irradiation conditions, it is possible to cure with an active energy ray even when the catalyst is not contained.

The thickness of the hard coat layer formed from the coating composition (A) is preferably 1 to 50 μm, and more preferably 1 to 50 μm.
-30 μm is preferred. Hard coat layer thickness is 50μ
If it exceeds m, curing by active energy rays will be insufficient, and the adhesion to the substrate will be easily impaired. If it is less than 1 μm, abrasion resistance and scratch resistance may be insufficient.

The plastic lens of the present invention can be manufactured, for example, as follows. The coating composition (A) is applied to the surface of the plastic lens substrate by the following method.
Hardens to form a hard coat layer. The hard coat layer may be formed on only one side of the substrate, or may be formed on both sides.

The method for applying the coating composition (A) is not particularly limited, and a known method can be employed. For example, dip coating, flow coating, spray coating,
Shower coating method, ring coating method, spin coating method,
Various methods such as an air knife method and a die coating method can be adopted. In the present invention, a method such as a dip coating method, a spin coating method, and a spray coating method is preferably employed from the viewpoint of productivity.

The method for curing the coating composition (A) includes the following methods (1) to (3). When the coating composition (A) contains a solvent, it is preferable that the coating composition is dried after application to remove the solvent, and then cured.

(1) After coating the coating composition (A), a sufficient amount of active energy rays are irradiated to terminate the curing of the polyfunctional compound, and then a partially cured or uncured polysilazane is obtained. Is heated, left at room temperature or exposed to the vapor of a curing catalyst solution of polysilazane to cure.

(2) After coating the coating composition (A),
Heating the uncured polysilazane, leaving it at room temperature or curing it by exposing it to the vapor of a curing catalyst solution of polysilazane,
Then, a sufficient amount of active energy rays is irradiated to cure the polyfunctional compound.

(3) After coating the coating composition (A),
By irradiating a sufficient amount of active energy rays, the curing of the polyfunctional compound and the curing of the polysilazane are performed almost simultaneously. In this method, the curing of the polysilazane is usually slower than the curing of the polyfunctional compound, and it is considered that the curing is actually performed by the same process as the above (1).

The active energy rays are not particularly limited, and ultraviolet rays, electron beams or other active energy rays can be used. In the present invention, ultraviolet rays are preferred because the apparatus is simple and the productivity is excellent. As the ultraviolet light source, a xenon lamp, a pulse xenon lamp, a low-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a metal halide lamp, a carbon arc lamp, a tungsten lamp, and the like can be used.

In the present invention, the firing temperature of the polysilazane is preferably 180 ° C. or less from the viewpoint of the heat resistance of the substrate, and the curing is preferably performed in an atmosphere such as air, in which oxygen is present. By firing polysilazane, its nitrogen atoms are replaced with oxygen atoms to generate silica, and firing in an atmosphere containing sufficient oxygen forms a dense silica layer.

The hard coat layer formed as described above has excellent adhesion to a plastic lens substrate, and has a composition containing silica converted from polysilazane, so that it has an adhesion to an inorganic compound. Excellent. Therefore, physical vapor deposition methods such as sputtering and ion plating, and plasma CVD are performed on the surface of the hard coat layer.
Chemical vapor deposition method, such as wet coating, etc.
A function-imparting layer for imparting anti-reflection, water repellency and hydrophilicity can be formed.

[0051]

EXAMPLES The present invention will be described below with reference to Examples (Examples 1 to 8) and Comparative Examples (Example 9), but the present invention is not limited thereto. In Examples 1 to 4 and 9, as a substrate, a polycarbonate resin flat plate (thickness: 2 m) produced by injection molding was used.
m) and a lens (no power, thickness 2 mm), and in Examples 5 to 8, alkali washing (immersion in a 10% by mass aqueous sodium hydroxide solution at 60 ° C. for 5 minutes) as a pretreatment, followed by water washing.
A degreased (ultrasonic cleaning with isopropanol) CR39 resin flat plate (2 mm thick) and a lens (no power, 2 mm thick) were used. In addition, the measurement and evaluation of various physical properties of the samples obtained in each example were performed by the following methods, and the results are shown in Table 1.

[Initial haze value, abrasion resistance] When a flat sample is subjected to abrasion resistance test according to JIS-R3212, two CS-10F abrasion wheels are combined with a 500 g weight and rotated 500 times. Was measured with a haze meter. The haze was measured at four points on the wear cycle track, and the average value was calculated. The initial haze value indicates the haze value (%) before the abrasion test, and the abrasion resistance indicates (haze value after the abrasion test)-(haze value before the abrasion test) (%).

[Scratch resistance (steel wool test)] # 0
A load of 2 kg was applied to 000 steel wool, and the surface of the hard coat layer of the sample (lens shape) was reciprocated 10 times to check for the presence or absence of scratches.

[Initial Yellowness] Using a color meter (manufactured by Suga Test Instruments Co., Ltd.), the yellowness (YI) values at two points of the plate-shaped sample were measured, and the average value was shown.

[Adhesion] The hard coat layer of the sample (flat plate and lens shape) was scribed 11 times each at 1 mm intervals with a razor blade to make 100 grids, and a commercially available cellophane tape was often used. After contact, 90
The number (m) of the grids left without peeling off the hard coat layer when the hard coat layer was suddenly peeled in the forward direction is represented by m / 100.

[Example 1] 2 equipped with a stirrer and a cooling pipe
In a 00 mL four-necked flask, 21.9 g of xylene, 14.9 g of dibutyl ether, 3.2 g of dipentaerythritol hexaacrylate, 4.8 g of tris (acryloyloxyethyl) isocyanurate, and 2-methyl-1
-{4- (methylthio) phenyl} -2-morpholinopropan-1-one 0.24 g, 2- [4-[(2-hydroxy-3-dodecyloxypropyl) oxy] -2-
Hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine and 2- [4-
[(2-hydroxy-3-tridecyloxypropyl)
[Oxy] -2-hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 0.4 g, N-methyl-4-methacryloyloxy-2,2,6 , 6-Tetramethylpiperidine
08 g was added and stirred at room temperature for 1 hour to dissolve.

Further, a xylene solution of perhydropolysilazane which is curable at a low temperature (solid content: 20% by mass, manufactured by Tonen Co., Ltd.)
10 g of trade name "D110") was added thereto, and the mixture was stirred at room temperature for 1 hour under a nitrogen atmosphere to obtain a coating liquid 1.

Each of the substrates was coated with the coating liquid 1 by a spin coating method (wet thickness: 15 μm), kept in a hot air circulating oven at 90 ° C. for 5 minutes, and then dried in an air atmosphere.
1000 mJ / cm ² (wavelength 300) using a high pressure mercury lamp
UV integrated energy in the region of 390 nm, the same applies hereinafter. The sample was irradiated with the ultraviolet light of (2) and kept in a hot-air circulating oven at 100 ° C. for 20 minutes to be sufficiently cured to obtain a sample having a hard coat layer having a thickness of 3 μm formed on the surface of the substrate.

Example 2 The sample preparation method in Example 1 was changed as follows. That is, instead of holding in a hot air circulating oven at 100 ° C. for 20 minutes, a sample was obtained by curing for 1 day in an environment of 23 ° C. and 55% relative humidity.

Example 3 The sample preparation method in Example 1 was changed as follows. That is, after holding for 20 minutes in a hot air circulating oven at 100 ° C., use a high pressure mercury lamp for 1 minute.
A sample was obtained by irradiating 000 mJ / cm ² with ultraviolet rays.

Example 4 2 equipped with a stirrer and a cooling pipe
In a 00 mL four-necked flask, 22.3 g of xylene, 15.1 g of dibutyl ether, 3.6 g of dipentaerythritol hexaacrylate, 5.4 g of tris (acryloyloxyethyl) isocyanurate, and 2-methyl-1
-{4- (methylthio) phenyl} -2-morpholinopropan-1-one 0.27 g, 2- [4-[(2-hydroxy-3-dodecyloxypropyl) oxy] -2-
Hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine and 2- [4-
[(2-hydroxy-3-tridecyloxypropyl)
[Oxy] -2-hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 0.5 g, N-methyl-4-methacryloyloxy-2,2,6 , 6-Tetramethylpiperidine
08 g was added and stirred at room temperature for 1 hour to dissolve.

Further, 5 g of low-temperature curable perhydropolysilazane “D110” was added, and the mixture was stirred at room temperature for 1 hour under a nitrogen atmosphere to obtain a coating liquid 2. A sample was obtained in the same manner as in Example 1, except that the coating liquid 2 was used instead of the coating liquid 1.

Example 5 2 equipped with a stirrer and a cooling pipe
In a 00 mL four-necked flask, 36.8 g of xylene, 3.2 g of dipentaerythritol hexaacrylate, 4.8 g of tris (acryloyloxyethyl) isocyanurate, 2-methyl-1- {4- (methylthio) phenyl} -2 Morpholinopropan-1-one 0.24
g, 2- [4-[(2-hydroxy-3-dodecyloxypropyl) oxy] -2-hydroxyphenyl]-
4,6-bis (2,4-dimethylphenyl) -1,3
5-triazine and 2- [4-[(2-hydroxy-3-
Tridecyloxypropyl) oxy] -2-hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine mixture 0.4 g, N-
Methyl-4-methacryloyloxy-2,2,6,6-
0.08 g of tetramethylpiperidine was added and dissolved by stirring at room temperature for 1 hour.

Further, 10 g of a low-temperature curable perhydropolysilazane “D110” was added to the mixture at room temperature under a nitrogen atmosphere.
After stirring for an hour, a coating liquid 3 was obtained.

Each substrate was coated with the coating solution 3 by spin coating (wet thickness: 15 μm), kept in a hot-air circulating oven at 100 ° C. for 5 minutes, and then in an air atmosphere using a high-pressure mercury lamp. Irradiate with 1000 mJ / cm ² of ultraviolet light, and then in a hot air circulating oven at 100 ° C. for 20 minutes.
After holding the sample for 3 minutes, a sample in which a hard coat layer having a thickness of 3 μm was formed on the substrate surface was obtained.

Example 6 The sample preparation method in Example 5 was changed as follows. That is, instead of holding in a hot air circulating oven at 100 ° C. for 20 minutes, a sample was obtained by curing for 1 day in an environment of 23 ° C. and 55% relative humidity.

[Example 7] 2 equipped with a stirrer and a cooling pipe
In a 00 mL four-necked flask, 41.4 g of xylene, 3.6 g of dipentaerythritol hexaacrylate, 5.4 g of tris (acryloyloxyethyl) isocyanurate, 2-methyl-1- {4- (methylthio) phenyl} -2 Morpholinopropan-1-one 0.27
g, 2- [4-[(2-hydroxy-3-dodecyloxypropyl) oxy] -2-hydroxyphenyl]-
4,6-bis (2,4-dimethylphenyl) -1,3
5-triazine and 2- [4-[(2-hydroxy-3-
0.5 g of a mixture of tridecyloxypropyl) oxy] -2-hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, N-
Methyl-4-methacryloyloxy-2,2,6,6-
0.08 g of tetramethylpiperidine was added and dissolved by stirring at room temperature for 1 hour.

Further, 5 g of low-temperature curable perhydropolysilazane “D110” was added, and the mixture was stirred at room temperature for 1 hour under a nitrogen atmosphere to obtain a coating liquid 4. A sample was obtained in the same manner as in Example 5, except that the coating liquid 4 was used instead of the coating liquid 3.

Example 8 The sample preparation method in Example 7 was changed as follows. That is, instead of holding in a hot air circulating oven at 100 ° C. for 20 minutes, a sample was obtained by curing for 1 day in an environment of 23 ° C. and 55% relative humidity.

[Example 9] A primer (trade name "PC-7" manufactured by Shin-Etsu Chemical Co., Ltd.) was applied to each substrate by spin coating.
A ”) (wet thickness 20 μm), and kept in a hot air circulating oven at 120 ° C. for 10 minutes to remove the solvent.
A primer layer (2 μm in thickness) was formed. Then, a silicone hard coat (trade name “KP8” manufactured by Shin-Etsu Chemical Co., Ltd.)
5 ") (wet thickness: 15 μm), and cured by holding in a hot air circulating oven at 120 ° C. for 60 minutes to obtain a sample.

[0071]

[Table 1]

[0072]

According to the present invention, it is possible to provide a plastic lens having a hard coat layer which has high productivity and is excellent in abrasion resistance, scratch resistance and transparency.

Claims (3)

[Claims] 1. A plastic lens having a hard coat layer on at least one surface of a plastic lens substrate, wherein the hard coat layer comprises a polyfunctional compound having two or more active energy ray-curable polymerizable functional groups, and a polysilazane. A plastic lens, which is a cured product layer of a coating composition (A) containing: 2. The hard coat layer has a thickness of 1 to 50 μm.
The plastic lens according to claim 1, wherein m is m. 3. A method for producing a plastic lens having a hard coat layer on at least one surface of a plastic lens substrate, comprising: a plastic lens substrate having at least one active energy ray-curable polymerizable functional group on at least one surface. A coating composition (A) containing a functional compound and polysilazane is applied, and then curing of the polyfunctional compound by irradiation with active energy rays and curing of the polysilazane are performed in any order or simultaneously. Forming a cured layer of the coating composition (A).