JPH08176206A - Production of plastic lens - Google Patents

Abstract

PURPOSE: To provide a process for producing a plastic lens, whereby a plastic lens free from turbidity and coloration can be produced, the resistance of the lens to attack by a polymerizable monomer is excellent and the lens can be produced in good yields because a gasket which easily follows the polymerization shrinkage of the lens resin during the cast polymerization. CONSTITUTION: A polymerizable monomer is cast-polymerized in a casting mold sealed with a gasket made of an ethylene/α-olefin copolymer having such properties that the drop (%) of transmittance of the polymerizable monomer to light of 400nm is 0.5% or below when 1 pt.wt. polymer is immersed in 5 pts.wt. polymerizable monomer at 40 deg.C for 6hr or an ethylene/α-olefin copolymer showing a heat of melting of below 10 J/g at 100 deg.C when measured with a differential scanning calorimeter.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a method of manufacturing a plastic lens.

[0002]

2. Description of the Related Art Conventionally, as materials for optical lenses, highly transparent acrylic resin, diethylene glycol bisallyl carbonate resin (for example, CR-39), polystyrene,
Polycarbonate and the like are used, but among these, a lens that uses diethylene glycol bisallyl carbonate, which is a thermosetting resin, is widely used as a spectacle lens. The reason is that it is excellent in transparency, low dispersibility (high Abbe number), heat resistance and impact resistance.

However, the lens using diethylene glycol bisallyl carbonate has a problem that the refractive index is as low as 1.50 and the thickness of the lens is larger than that of the glass lens (particularly, it is remarkable when the lens power is large). . Further, it is inferior in scratch resistance like general plastics. For this reason, a method of coating the lens surface with an organic silane-based hard coat film has been proposed, but in the untreated state, uniform adhesion to the organic silane-based hard coat film is insufficient. Therefore, the surface of the plastic lens cannot be coated with the organic silane-based hard coat film unless the surface of the plastic lens is treated by any method.

Recently, there has been a strong demand for thinner and lighter spectacle lenses, and development of materials for spectacle lenses having a high refractive index, which makes it possible, has been actively pursued. Particularly, development of a high refractive index material in which an aromatic monomer is copolymerized as a polymerizable monomer is actively underway (Japanese Patent Laid-Open Nos. 58-76410 and 60-28412, Kaihei 3-136
002, JP-A-3-256001, JP-A-5-5011). On the other hand, a plastic lens is generally manufactured by injecting a polymerizable monomer into a plastic lens casting mold composed of two glass molds and a gasket and curing it by heating or the like. However, since the aromatic monomer used in the high refractive index material has a greater erosion property with respect to the gasket than diethylene glycol bisallyl carbonate, etc.,
When casting polymerization is performed using a gasket made of ethylene-vinyl acetate copolymer, ethylene-ethyl acrylate copolymer, etc., which is the gasket material currently commonly used, The additive or low molecular weight substance is eluted, and the resulting lens becomes cloudy or colored.

In order to improve such problems, recently, gaskets having excellent erosion resistance against polymerizable monomers such as aromatic monomers have been actively developed. For example, JP-A-2-128810 proposes a gasket made of a silicone-containing elastomer. However, this gasket has insufficient resistance to corrosion by the polymerizable monomer and is expensive. Also, Japanese Patent Application Laid-Open
JP-A-112408 proposes a gasket made of a fluorine-containing elastomer. Although this gasket has excellent erosion resistance to polymerizable monomers, it is extremely expensive and extremely difficult to industrially use.

Further, JP-A-3-173613 proposes a method of coating the surface of a gasket with a thermoplastic polyamide. When this method is used, although the erosion resistance of the gasket to the polymerizable monomer is improved, when the gasket is peeled off from the glass mold or the plastic lens after the completion of the casting polymerization, the thermoplastic polyamide is mixed with the glass mold or the plastic lens. However, there is a problem that it is difficult to remove it because some of it remains.

Although a gasket made of polyethylene has been proposed in the past (see Japanese Patent Laid-Open No. 51-4260, etc.), this gasket also has insufficient erosion resistance to polymerizable monomers. Furthermore, because the flexibility is remarkably lacking,
The sealability will be poor, and the gasket will not be able to follow the polymerization shrinkage of the lens resin during casting polymerization, and sink marks will easily occur on the lens surface.

Further, Japanese Patent Laid-Open No. 61-125814 discloses a low molecular weight product having a number average molecular weight of 5,000 to 50,000 and a number average molecular weight of 1,000 or less.
Gaskets consisting of less than 0 wt% polyethylene have been proposed. This gasket is still insufficient in erosion resistance with respect to the polymerizable monomer, and the lens tends to become cloudy. Furthermore, the flexibility is not improved at all compared to conventional polyethylene gaskets, so the sealability deteriorates, and the gasket cannot follow the polymerization shrinkage of the lens resin during casting polymerization, causing sink marks on the lens surface. Such problems are likely to occur.

Further, in JP-A-2-185586, the density is 0.87 to 0.91 g / cm ³ , and the maximum melting peak temperature measured by a differential scanning calorimeter (DSC) is 10
A gasket made of an ethylene-α-olefin copolymer resin having a temperature of 0 ° C or higher and a heat of fusion of 110 ° C or higher by DSC of 10 Joule / g or higher has been proposed. This gasket contains polymerizable monomer at 100 ~ 130 ℃
The purpose is to improve the heat resistance of the gasket during cast polymerization at high temperature, and the corrosion resistance to aromatic monomers is poor. Therefore, when a polymerizable monomer containing an aromatic monomer is cast-polymerized by using this gasket, a noticeable white turbidity occurs in the lens. Further, since this gasket has a very high melting temperature, the gasket does not soften sufficiently at about 40 to 90 ° C at which the lens resin containing the aromatic monomer or the like polymerizes and shrinks during the casting polymerization. For this reason, the gasket is unable to follow the polymerization shrinkage of the lens resin during the casting polymerization, and problems such as sink marks on the lens surface tend to occur.

As described above, conventionally, there has been no gasket excellent in corrosion resistance to a polymerizable monomer. The reason for this is a method for easily and accurately evaluating the corrosion resistance of a gasket material to a polymerizable monomer. There was no such thing. That is, conventionally, when evaluating the erosion resistance of a gasket to a polymerizable monomer, first a mold is designed according to each gasket material, and then the gasket is injection-molded using this mold. A complicated evaluation method of injecting a polymerizable monomer into a casting mold composed of a gasket and a glass mold, manufacturing a plastic lens by curing by heating, etc., and evaluating its cloudiness or coloring state was used. . Therefore, it could take weeks to evaluate a single gasket, and even months to long. Further, in Japanese Patent Laid-Open No. 61-114816, in evaluating the erosion resistance of a gasket material to a polymerizable monomer,
Although an evaluation method is used to measure the swelling ratio of the gasket material with the polymerizable monomer after the gasket material is immersed in the polymerizable monomer, this evaluation method uses a small amount of the polymerizable monomer in the gasket. Optical haze and coloring due to elution of additives and low molecular weight substances cannot be detected.
For this reason, the polymerizable monomer was actually injected into the casting mold composed of the gasket and the glass mold, and the plastic lens was manufactured by curing it by heating, etc., and the result of evaluating the opaque or colored state and the above method The results of the erosion resistance evaluation of the gaskets do not always match.

As described above, a method for easily and accurately evaluating the erosion resistance of a gasket material with respect to a polymerizable monomer, a gasket material excellent in erosion resistance, and a high refractive index plastic lens using the same have been heretofore used. There was no manufacturing method.

On the other hand, recently, from the viewpoint of reducing the weight of spectacle lenses, materials for spectacle lenses having a low specific gravity have been actively developed. For example, JP-A-2-238006 proposes an acrylic resin using 2,2-dialkyl-1,3-propanedi (meth) acrylate. However, this material still has a large specific gravity of 1.31 to 1.35,
Moreover, the dyeability and the adhesiveness to the organic silane-based hard coat film are poor. Further, JP-A-5-215903 discloses a copolymer of di (meth) acrylate having a linear alkyl group as a spacer / (meth) acrylate having an alkyl group / aromatic vinyl compound / other monomer. Proposed. Although this material has a low specific gravity, it has a low heat resistance temperature and is therefore easily deformed during dyeing or hard coating. Further, all of these materials have insufficient strength and have a drawback that they are easily damaged during drilling.

Further, in Japanese Patent Application Laid-Open No. 4-126710, a bifunctional (meth) containing an alkylene oxide group is described.
A copolymer of acrylate / aromatic vinyl monomer / polymerizable double bond-containing polymerizable monomer or polymerizable oligomer having a molecular weight of 98 or more has been proposed. This material has a drawback that the low specific gravity is still insufficient and the hue tends to be yellowish.

Further, as a resin having improved adhesiveness to a hard coat film, a copolymer of aromatic ring-containing dimetha (acrylate) / aromatic ring-containing monomer / hydroxyl group-containing monomer (JP-A-58-58). No. 76410), and a copolymer of aromatic ring-containing dimetha (acrylate) / aromatic ring-containing monomer / epoxy group-containing monomer (see JP-A-58-89606). However, although these materials improve the adhesiveness to the glass film when glass is vapor-deposited, the adhesiveness to the organic silane-based hard coat film is not yet satisfactory. Furthermore, the latter is not preferable from the viewpoint of moldability because the adhesiveness of the cast polymerization to the glass mold increases excessively as the copolymerization amount of the epoxy group-containing monomer in the resin increases.

As described above, until now, it has been excellent in erosion resistance against polymerizable monomers such as aromatic monomers,
Moreover, there has been no manufacturing method for producing a plastic lens having a high refractive index at a low cost and a high yield by using a gasket which easily follows the polymerization shrinkage of the lens resin during the casting polymerization.

[0016]

SUMMARY OF THE INVENTION An object of the present invention is to provide a method for producing a plastic lens free from cloudiness and coloring. Further, an object of the present invention is to use a gasket that is excellent in erosion resistance to a polymerizable monomer including an aromatic monomer, and that easily follows the polymerization shrinkage of the lens resin during cast polymerization, It is intended to provide a manufacturing method capable of manufacturing a plastic lens at a low cost and a high yield. Another object of the present invention is to provide a manufacturing method capable of inexpensively producing a plastic lens having a high refractive index using the above-mentioned gasket and having a good balance of hue, strength at the time of punching, and specific gravity at a high yield. To provide.

[0017]

[Problems to be Solved by the Invention] The method for producing a plastic lens according to the present invention is as follows. When manufacturing the above, a gasket made of an ethylene-α-olefin copolymer is used.

In the present invention, as the ethylene-α-olefin copolymer, 1 part by weight of 5 parts by weight of the polymerizable monomer is immersed in a polymerizable monomer at 400 nm for 6 hours at 40 ° C. The degree of decrease in the light transmittance of the body (%) is 0.5%
What is below or by differential scanning calorimeter (DSC) 1
The heat of fusion at 00 ° C or higher is less than 10 Joule / g, but it is used. The degree of decrease in light transmittance (%) is a value obtained by subtracting the light transmittance (%) of the polymerizable monomer after the gasket material is immersed from the light transmittance (%) of the polymerizable monomer before the gasket material is immersed. Is. However, the light transmittance is 10
The values are measured when a quartz glass cell of mm is used and the light transmittance thereof is set to 100% with air as a reference.
The heat of fusion at 100 ° C. or higher measured by a differential scanning calorimeter (DSC) is measured according to JIS-K7122.

The above-mentioned ethylene-α-olefin copolymer has ethylene and carbon atoms of 3 to 1 using a Ziegler catalyst or the like.
It is obtained by copolymerizing the α-olefin of 8.
Examples of Ziegler catalysts include vanadium-based catalysts. As the α-olefin, propylene, 1-butene, 1-pentene, 1-hexene, 4-methyl-1-
3 to 3 carbon atoms such as pentene, 1-octene, 1-decene
There are 18 α-olefins, which are used alone or in combination of two or more. As the α-olefin, those having 3 to 10 carbon atoms are preferable among the above examples.

In the above-described method for producing a plastic lens, 1 part by weight of an ethylene-α-olefin copolymer is immersed in 5 parts by weight of a polymerizable monomer at 40 ° C. for 6 hours to obtain a polymerizable monomer at 400 nm. The degree of decrease (%) in light transmittance of the body is preferably 0.5% or less. When the degree of decrease in the light transmittance of the polymerizable monomer exceeds 0.5%, the plastic lens obtained by the cast polymerization tends to be clouded or colored. In order to further reduce clouding and coloring of the plastic lens and obtain a plastic lens with good transparency, the degree of decrease in the light transmittance of the polymerizable monomer is 0.3.
% Or less is particularly preferable.

Ethylene-based on 5 parts by weight of the polymerizable monomer.
of the ethylene-α-olefin copolymer used for measuring the degree of decrease (%) in the light transmittance of the polymerizable monomer at 400 nm when 1 part by weight of the α-olefin copolymer is immersed for 6 hours at 40 ° C. The shape and size are not particularly limited, but in order to select the ethylene-α-olefin copolymer for obtaining the above effects, particles or powders having a maximum length of 1 to 5 mm (for example, pellets It is preferable to use a material having a shape of It is particularly preferable that the maximum size is about 3 to 4 mm. When measuring the light transmittance of the polymerizable monomer after the gasket material is immersed, it is necessary to remove the gasket material pellets from the polymerizable monomer by filtration or the like.

The reason why the measuring temperature is 40 ° C. when measuring the degree of decrease in the light transmittance of the above-mentioned polymerizable monomer is that it is generally poured at about 25 to 50 ° C. in the above-mentioned plastic lens manufacturing method. Initiating mold polymerization may be mentioned. When measuring the degree of decrease in light transmittance, if the measurement temperature is too high or too low, the polymerizable monomer is actually injected into the plastic lens casting mold that is sealed with a gasket, and casting polymerization is performed. There is a possibility that the result of evaluating the cloudiness or the coloring state of the plastic lens manufactured by performing the above and the result of the evaluation of the erosion resistance of the gasket by the above method may not match.

When measuring the degree of decrease in light transmittance of the above-mentioned polymerizable monomer, the reason for setting the measurement wavelength to 400 nm is that additives and low molecular weight substances in the gasket are eluted in the polymerizable monomer. When doing so, first, a decrease in light transmittance occurs at 300 to 400 nm. Measurement wavelength is 40
By setting the thickness to 0 nm, slight clouding or coloring of the polymerizable monomer can be accurately detected.

The above ethylene-α olefin copolymer has a melting calorie (JIS-K7122) of 100 joules or more measured by a differential scanning calorimeter (DSC) of 10 Joules /
It is preferably less than g. When the heat of fusion (JIS-K7122) of 100 ° C. or higher is 10 Joules / g or higher, the gasket is formed at about 40 to 90 ° C. in which the lens resin containing the aromatic monomer or the like polymerizes and shrinks during the casting polymerization. Does not soften sufficiently. For this reason, the gasket is unable to follow the polymerization shrinkage of the lens resin during the casting polymerization, and problems such as sink marks on the lens surface tend to occur.

The ethylene-α-olefin copolymer used in the gasket material is 400 nm when 1 part by weight of 5 parts by weight of the polymerizable monomer is immersed at 40 ° C. for 6 hours.
The degree of decrease (%) in light transmittance of the polymerizable monomer at 0.5 is 0.5.
% Or less, and the heat of fusion at 100 ° C. or higher measured by a differential scanning calorimeter (DSC) is preferably less than 10 Joules / g.

The above ethylene-α-olefin copolymer preferably has a density of 0.85 to 0.91 g / cm ³ . When the density exceeds 0.91 g / cm ³ , the flexibility is deteriorated, the sealing property is deteriorated, and the gasket cannot follow the polymerization shrinkage of the lens resin during casting polymerization, and sink marks are apt to occur on the lens surface. Also, the density is 0.8
If it is less than 5 g / cm ^3, it is too soft, and it becomes difficult to stably maintain a predetermined lens shape during the casting polymerization of the polymerizable monomer, and the heat resistance is liable to be lowered and the resin melts during the casting polymerization. Cheap. It is particularly preferable that the density is 0.87 g / cm ³ or more in order to stably maintain a predetermined lens shape during casting polymerization of the polymerizable monomer and sufficiently maintain heat resistance.

The above ethylene-α-olefin copolymer has an ethylene-density of 0.85 to 0.91 g / cm ^{3 in} order to balance the physical properties such as MFR and heat resistance.
A mixture of two or more α-olefin copolymers may be used.

The ethylene-α-olefin copolymer has a density of 0.85 to 0.91 in order to balance the physical properties such as melt flow rate (MFR) and heat resistance.
A mixture of an ethylene-α olefin copolymer having a density of g / cm ^{3 and} an ethylene-α olefin copolymer having a density of 0.91 to 0.94 may be used. The density is 0.85 to 0.
91 g / cm ³ of ethylene-α olefin copolymer is 7
If it is less than 0% by weight, the flexibility is lowered, the sealing property is deteriorated, and the gasket cannot follow the polymerization shrinkage of the lens resin during the casting polymerization, and the sink mark is apt to occur on the lens surface. In order to keep the flexibility high enough, the density is 0.
It is particularly preferable that the ethylene-α-olefin copolymer of 85 to 0.91 g / cm ³ is 80% by weight or more.

In the above-mentioned method for producing a plastic lens, the ethylene-α-olefin copolymer can be processed into a gasket shape by injection molding, compression molding, extrusion molding or the like. It is preferable to process it.

The above-mentioned ethylene-α-olefin copolymer has an MFR (ASTM D1238, E) of 3 to 100 g / 10.
Minutes are preferred. If the MFR is less than 3 g / 10 minutes, it becomes difficult to process it into a gasket shape by injection molding. If it exceeds 100 g / 10 minutes, the heat resistance tends to decrease. The MFR is more preferably 5 g / 10 minutes or more, and particularly preferably 8 g / 10 minutes or more, in order to sufficiently improve the workability in injection molding into a gasket shape. Also, to maintain heat resistance sufficiently high, MF
It is particularly preferable that R is 50 g / 10 minutes or less.

As the above-mentioned ethylene-α-olefin copolymer, one having a JIS A hardness of 50 or more and 95 or less is preferable. When the JIS A hardness is less than 50, it becomes difficult to stably maintain a predetermined lens shape during cast polymerization of the polymerizable monomer. For the same reason, JIS A hardness of 70 or more is particularly preferable. Further, if the JIS A hardness exceeds 95, the sealability tends to be poor, or the gasket cannot follow the polymerization shrinkage of the lens resin during the casting polymerization, and the sink mark is likely to occur on the lens surface.

In the above-described method for producing a plastic lens, the polymerizable monomer mixture containing a polymerization initiator is added to
It is poured into a mold composed of a sheet of glass and a gasket, and if necessary, fixed with a spring-loaded clip or the like, and then cured by heating. A molecular weight modifier may be added to the polymerizable monomer mixture.

In the above-mentioned method for producing a plastic lens, it is preferable that cast polymerization is carried out in the range of 10 to 100 ° C., and after the polymerization is completed, the plastic lens is released from the casting mold. If the temperature at the time of cast polymerization is 10 ° C. or lower, the radical generator added as a polymerization initiator is not sufficiently decomposed, and the polymerization is likely not to proceed sufficiently. Further, if the temperature during the casting polymerization exceeds 100 ° C., the gasket made of the ethylene-α-olefin copolymer is likely to melt during the casting polymerization. In order for the radical generator added as a polymerization initiator to be sufficiently decomposed and the polymerization to proceed sufficiently, the temperature during casting polymerization is 1
It is preferably 5 ° C. or higher, particularly preferably 20 ° C. or higher. Further, the temperature during the casting polymerization is preferably 95 ° C. or lower so that the gasket made of the ethylene-α-olefin copolymer does not melt during the casting polymerization.
Casting polymerization is performed in order to prevent the polymerizable monomer from eroding the gasket and to reduce the internal strain at the time of polymerization.
It is preferable to start the polymerization at a relatively low temperature of 0 to 50 ° C., gradually raise the temperature, and finish the polymerization at 60 to 100 ° C. For the same reason, polymerization was started at 20 to 40 ° C and the temperature was gradually raised to 7
It is particularly preferable to complete the polymerization at 0 to 90 ° C.

In the above-mentioned method for producing a plastic lens, it is preferable that after the completion of the casting polymerization, the plastic lens is released from the casting mold and then heat-treated at 90 to 140 ° C. for 1 to 2 hours. As a result, the internal strain generated during the cast polymerization can be relaxed and the residual monomer can be reduced.

In the above-mentioned method for producing a plastic lens, as the polymerization initiator used at the time of polymerization, those generally used for radical polymerization can be used as they are. For example, 1,1-bis (t-butylperoxy)
3,3,5-Trimethylcyclohexane, 1,1-bis (t-butylperoxy) cyclohexane, n-butyl-4,4'-bis (t-butylperoxy) valerate, decanoyl peroxide, lauroyl peroxide , Benzoyl peroxide, m-toluoyl peroxide, acetylcyclohexyl sulfonyl peroxide, diisopropyl peroxydicarbonate,
Di-2-ethylhexyl peroxy dicarbonate, di-normal propyl peroxy dicarbonate, dimethoxy isopropyl peroxy dicarbonate, cumyl peroxy neodecanoate, t-butyl peroxypivalate, t-butyl peroxy-2-ethyl Organic peroxides such as hexanoate, t-butylperoxy-3,5,5-trimethylhexanoate, di-t-butyldiperoxyisophthalate, t-butylperoxyisopropyl carbonate, 2,2′- Azobis (isobutyronitrile), 2,2'-azobis (4-methoxy-2,4-
Dimethylvaleronitrile), 2,2′-azobis (2,2
4-dimethylvaleronitrile), dimethyl-2,2'-
Azobisisobutyrate, 2,2'-azobis (2-methylbutyronitrile), 1,1'-azobis (1-cyclohexanecarbonitrile), 2-phenylazo-2,
4-dimethyl-4-methoxyvaleronitrile, 2,2 '
Examples thereof include azo-based polymerization initiators such as azobis (2-methylpropane). Two or more of these polymerization initiators may be used in combination. Also, a tertiary amine, a metal salt or the like can be used together as an accelerator.

As the polymerization initiator used in the above-mentioned polymerization, acetylcyclohexyl sulfonyl peroxide, diisopropyl peroxydicarbonate, di-2-ethylhexyl peroxydicarbonate, dinormal propyl are included in the above-mentioned examples. Peroxydicarbonate, dimethoxyisopropyl peroxydicarbonate, cumyl peroxy neodecanoate, t
It is preferable to contain at least one organic peroxide having a 10-hour half-life temperature of 20 to 60 ° C., such as butylperoxypivalate, and especially acetylcyclohexylsulfonyl peroxide, diisopropylperoxydicarbonate, di-2-ethylhexyl. At least one organic peroxide having a 10-hour half-life temperature of 20 to 50 ° C., such as peroxydicarbonate, dinormal propyl peroxydicarbonate, dimethoxyisopropyl peroxydicarbonate, cumylperoxy neodecanoate, etc., may be contained. Particularly preferred.

The polymerization initiator used in the above-mentioned polymerization is
By including at least one organic peroxide having a 10-hour half-life temperature of 20 to 60 ° C., the polymerization at a relatively low temperature of about 10 to 50 ° C. is sufficiently advanced, and the viscosity of the polymerizable monomer is sufficiently increased. can do. This makes it possible to prevent the polymerizable monomer from eroding the gasket when the temperature is raised to a relatively high polymerization temperature of 60 to 100 ° C. In order to prevent the polymerizable monomer from eroding the gasket, the polymerization initiator has a 10-hour half-life temperature of 20 or less.
It is preferable to contain 1 to 100% by weight of an organic peroxide at -60 ° C, more preferably 30 to 100%, and 5
It is particularly preferable to contain 0 to 100% by weight. In addition, when an organic peroxide having a 10-hour half-life temperature of 20 to 60 ° C is used, compared with the case of using another polymerization initiator (azo-based initiator) having a 10-hour half-life temperature of 20 to 60 ° C. As a result, cracks and bubbles are less likely to occur inside the plastic lens.

The polymerization initiator used in the above-mentioned polymerization is
It is preferable to add 0.01 to 10 parts by weight to 100 parts by weight of the polymerizable monomer. The amount of the polymerization initiator blended is 0.
If it is less than 01 parts by weight, the polymerization may not proceed sufficiently. For the same reason, the amount of the polymerization initiator compounded is preferably 0.1 part by weight or more, and particularly preferably 0.5 part by weight or more. Further, if the amount of the polymerization initiator compounded exceeds 10 parts by weight, the heat of polymerization will be large and it will be difficult to control the polymerization, and the physical properties of the resulting lens will tend to deteriorate. For the same reason, the compounding amount of the polymerization initiator is preferably 5 parts by weight or less, and particularly preferably 3 parts by weight or less.

In the above-mentioned method for producing a plastic lens, a general chain transfer agent, mercaptans, dialkyldisulfides, chloroform, carbon tetrachloride and the like can be used as a molecular weight modifier which may be used at the time of polymerization. Considering the transparency, color, heat resistance and the like of the plastic lens, the dimer of α-methylstyrene is preferable. The molecular weight modifier is used in an amount of 0.1 to 10% by weight based on the total monomers. If it is less than 0.1% by weight, the haze value tends to be high, foreign matter is generated on the resin surface, coloring is likely to occur, and the strength tends to be lowered. A problem such as a decrease occurs. For the same reason, it is particularly preferable to use the molecular weight modifier in an amount of 0.5 to 5% by weight with respect to the monomer.

In the above-mentioned method for producing a plastic lens, from the viewpoints of preventing coloration, shortening the polymerization induction period, etc., oxygen in the polymerizable monomer was 1.0 mg / l by nitrogen bubbling.
After reducing the amount to the following, it is preferable to inject a polymerizable monomer into a casting mold and perform casting polymerization. Further, from the viewpoint of preventing coloring, when the plastic lens is released from the mold after the casting polymerization and heat-treated at 90 to 140 ° C. for 1 to 2 hours,
It is preferable to perform the heat treatment in an inert gas atmosphere.

In the above-mentioned method for producing a plastic lens, from the viewpoint of shortening the polymerization time and reducing the gasket erosion of the polymerizable monomer, the polymerizable monomer is prepolymerized to form a prepolymer, and then a polymerization initiator is added. In addition, a polymerizable monomer can be injected into a casting mold to perform casting polymerization.
At this time, the above-mentioned molecular weight modifier can be added before or after the prepolymerization, but it is preferable to add it before the prepolymerization in consideration of transparency as a plastic lens.

The above-mentioned polymerizable monomer preferably contains at least one aromatic monomer. Further, the polymerizable monomer is represented by 1 to 50 parts by weight of a monomer containing an alkylene oxide group represented by Chemical formula 3 [general formula (I)] and Chemical formula 4 [general formula (II)]. 1 to 50 parts by weight of polyfunctional (meth) acrylate, 15 to 60 of styrene
0 to 60 parts by weight and other copolymerizable vinyl monomers
It is preferable that the monomer mixture is such that 100 parts by weight of the whole is mixed.

Embedded image R ¹ —O— (R ² O) m —R ³ ... (I) (wherein R ¹ is an acryloyl group or a methacryloyl group, and R ² has 1 to 40 carbon atoms, particularly preferably 1 ~
Is an alkylene group which is 5, R ³ is hydrogen, an acryloyl group, a methacryloyl group or a carbon number other than these 1 to 1
40 monovalent hydrocarbon groups, m is an integer of 9 to 50)

[Chemical 4] (However, R ⁴ and R ⁵ are each independently an acryloyl group,
Or a methacryloyl group, and R ⁶ and R ⁷ are each independently a monovalent hydrocarbon group having 1 to 6 carbon atoms)

Examples of the above-mentioned aromatic monomers include styrene, α-methylstyrene, α-ethylstyrene, α-fluorostyrene, α-chlorostyrene, α-bromostyrene, α-iodostyrene, fluorostyrene and chloro. Styrene derivatives such as styrene, bromostyrene, iodostyrene, dichlorostyrene methylstyrene, methoxystyrene, etc., aromatic methacrylates such as phenyl methacrylate, chlorophenyl methacrylate, benzyl methacrylate, chlorobenzyl methacrylate, phenoxyethyl methacrylate, phenyl acrylate, chlorophenyl Aromatic acrylates such as acrylate, benzyl acrylate, chlorobenzyl acrylate, phenoxyethyl acrylate, diallyl orthophthalate, diallyl isophthalate Over DOO, diallyl terephthalate, tetrabromobisphenol diallylorthophthalate, tetrabromobisphenol diallyl isophthalate, etc. tetrabromobisphenol diallyl terephthalate.

Among the above examples, styrene, α-methylstyrene, α-ethylstyrene, α-fluorostyrene, α-chlorostyrene, α from the viewpoint of refractive index and transparency.
Styrene derivatives such as -bromostyrene, α-iodostyrene, fluorostyrene, chlorostyrene, bromostyrene, iodostyrene, dichlorostyrenemethylstyrene and methoxystyrene are preferable, and among them, styrene is particularly preferable.

Examples of the alkylene oxide group-containing monomer represented by the general formula (I) include monofunctional monomers and polyfunctional monomers.

Among the monomers containing an alkylene oxide group represented by the general formula (I), the monofunctional monomer is nonamethylene glycol monoacrylate,
Polymethylene glycol monoacrylate such as tridecamethylene glycol monoacrylate, tetradecamethylene glycol monoacrylate, tricosamethylene glycol monoacrylate, nonamethylene glycol monomethacrylate, tridecamethylene glycol monomethacrylate, tetradecamethylene glycol monomethacrylate, tricosa Polymethylene glycol monomethacrylates such as methylene glycol monomethacrylate, methoxynonamethyleneglycol acrylate, methoxytridecamethyleneglycol acrylate, methoxytetradecamethyleneglycol acrylate, methoxytricosamethyleneglycol acrylate, ethoxynonamethyleneglycol acrylate, ethoxytridecamethyleneglycol Alkoxy polymethylene glycol acrylate such as acrylate, ethoxytetradecamethylene glycol acrylate, ethoxytricosamethylene glycol acrylate, methoxynonamethylene glycol methacrylate, methoxytridecamethylene glycol methacrylate, methoxytetradecamethylene glycol methacrylate, methoxytricosamethylene glycol methacrylate Alkoxy polymethylene glycol methacrylate such as ethoxy nonamethylene glycol methacrylate, ethoxy tridecamethylene glycol methacrylate, ethoxy tetradecamethylene glycol methacrylate, ethoxy tricosamethylene glycol methacrylate, nona ethylene glycol monoacrylate, trideca ethylene Polyethylene glycol monoacrylate such as recall monoacrylate, tetradecaethylene glycol monoacrylate, tricosa ethylene glycol monoacrylate, nonaethylene glycol monomethacrylate, tridecaethylene glycol monomethacrylate, tetradecaethylene glycol monomethacrylate, tricosa ethylene glycol monomethacrylate Such as polyethylene glycol monomethacrylate, methoxynonaethylene glycol acrylate, methoxytridecaethylene glycol acrylate, methoxytetradecaethylene glycol acrylate, methoxytricosa ethylene glycol acrylate, ethoxynonaethylene glycol acrylate, ethoxytridecaethylene glycol acrylate, Alkoxy polyethylene glycol acrylates such as ethoxy tetradeca ethylene glycol acrylate and ethoxy tricosa ethylene glycol acrylate,
Methoxynonaethylene glycol methacrylate, methoxytridecaethylene glycol methacrylate, methoxytetradecaethylene glycol methacrylate, methoxytricosa ethylene glycol methacrylate, ethoxynonaethylene glycol methacrylate, ethoxytridecaethylene glycol methacrylate, ethoxytetradecaethylene glycol methacrylate, ethoxytricosa Alkoxy polyethylene glycol methacrylate such as ethylene glycol methacrylate, nonapropylene glycol monoacrylate, polypropylene glycol monoacrylate such as dodecapropylene glycol monoacrylate, tridecapropylene glycol monoacrylate, nonapropylene glycol monomethacrylate, Decamethylene glycol monomethacrylate, polypropylene glycol monomethacrylate such as tridecanol propylene glycol monomethacrylate, methoxy nonapropylene glycol acrylate, methoxy dodeca propylene glycol acrylate, methoxy triethylene deca propylene glycol acrylate, ethoxy nonapropylene glycol acrylate,
Ethoxydodeca propylene glycol acrylate, alkoxy polypropylene glycol acrylate such as ethoxy trideca propylene glycol acrylate, methoxy nona propylene glycol methacrylate, methoxy dodeca propylene glycol methacrylate, methoxy trideca propylene glycol methacrylate, ethoxy nona propylene glycol methacrylate, ethoxy dodeca propylene glycol methacrylate, Alkoxy polypropylene glycol methacrylate such as ethoxytridecapropylene glycol methacrylate Nonabutylene glycol monoacrylate, polybutylene glycol monoacrylate such as dodecabutylene glycol monoacrylate, tridecabutylene glycol monoacrylate, Nabutylene glycol monomethacrylate, dodecabutylene glycol monomethacrylate, tridecabutylene glycol monomethacrylate, etc. polybutylene glycol monomethacrylate, methoxynonabutylene glycol acrylate, methoxydodecapbutylene glycol acrylate, methoxytridecabutylene glycol acrylate, ethoxynonabutylene glycol acrylate Alkoxypolybutylene glycol acrylate such as ethoxydodecapbutylene glycol acrylate, ethoxytridecabutylene glycol acrylate, methoxynonabutylene glycol methacrylate, methoxydodecapbutylene glycol methacrylate, methoxytridecabutylene glycol methacrylate, ethoxynonabutylene Cholemethacrylate, ethoxydodecabutylene glycol methacrylate, alkoxy polybutylene glycol methacrylate such as ethoxytridecabutylene glycol methacrylate, heptaethylene glycol glycol tripropylene glycol monoacrylate, nonaethylene glycol propylene glycol monoacrylate, tetradecaethylene glycol propylene glycol monoacrylate, Polyethylene glycol polypropylene such as nonaethylene glycol dipropylene glycol monoacrylate, tetradecaethylene glycol dipropylene glycol monoacrylate, nonaethylene glycol tripropylene glycol monoacrylate, tetradecaethylene glycol tripropylene glycol monoacrylate Recall monoacrylate, heptaethylene glycol tripropylene glycol monomethacrylate, nonaethylene glycol propylene glycol monomethacrylate, tetradecaethylene glycol propylene glycol monomethacrylate, nonaethylene glycol dipropylene glycol monomethacrylate, tetradecaethylene glycol dipropylene glycol monomethacrylate, Polyethylene glycol polypropylene glycol monomethacrylate such as nonaethylene glycol tripropylene glycol monomethacrylate and tetradecaethylene glycol tripropylene glycol monomethacrylate, polyethylene glycol polybutylene such as decaethylene glycol pentabutylene glycol monoacrylate Call monoacrylate, polyethylene glycol polybutylene glycol monomethacrylate such as decaethylene glycol pentaethylene butylene glycol monomethacrylate, and the like, which are used singly or in combination.

Among the above-mentioned examples, methoxynonaethylene glycol acrylate, methoxytridecaethylene glycol acrylate, methoxytetradecaethylene glycol acrylate, and methoxytricosaethylene glycol are preferred from the viewpoint of adhesion and dyeability to the organic silane-based hard coat film. Methoxy polyethylene glycol acrylate such as acrylate, ethoxy nonaethylene glycol acrylate, ethoxy trideca ethylene glycol acrylate, ethoxy tetradeca ethylene glycol acrylate, ethoxy trideca ethylene glycol acrylate and other ethoxy polyethylene glycol acrylate, methoxy nona ethylene glycol methacrylate, methoxy trideca Ethylene glycol methacrylate, methoxy Methoxy polyethylene glycol methacrylate such as tradeca ethylene glycol methacrylate and methoxy tricosa ethylene glycol methacrylate, ethoxy nona ethylene glycol methacrylate, ethoxy trideca ethylene glycol methacrylate, ethoxy tetradeca ethylene glycol methacrylate, and ethoxy polyethylene glycol such as ethoxy tricosa ethylene glycol methacrylate. Methacrylate and the like are preferred.

Among the above-mentioned alkylene oxide group-containing monomers represented by the general formula (I), polyfunctional monomers include nonamethylene glycol diacrylate, tridecamethylene glycol diacrylate and tetradecamethylene. Polymethylene glycol diacrylate such as glycol diacrylate, tricosamethylene glycol diacrylate, nonamethylene glycol dimethacrylate, tridecamethylene glycol dimethacrylate,
Polymethylene glycol dimethacrylate such as tetradecamethylene glycol dimethacrylate and tricosamethylene glycol dimethacrylate, polyethylene such as nonaethylene glycol diacrylate, tridecaethylene glycol diacrylate, tetradecaethylene glycol diacrylate and tricosa ethylene glycol diacrylate Polyethylene glycol dimethacrylate such as glycol diacrylate, nonaethylene glycol dimethacrylate, tridecaethylene glycol dimethacrylate, tetradecaethylene glycol dimethacrylate, tricosa ethylene glycol dimethacrylate, nonapropylene glycol diacrylate, dodecapropylene glycol diacrylate, tridecaethylene glycol dimethacrylate Decapropylene glycol di Polypropylene glycol diacrylate such as acrylate, nonapropylene glycol dimethacrylate, dodecapropylene glycol dimethacrylate, polypropylene glycol dimethacrylate such as tridecapropylene glycol dimethacrylate, nonabutylene glycol diacrylate, dodecabutylene glycol diacrylate, tridecabutylene glycol dimethacrylate Polybutylene glycol diacrylate such as acrylate, nonabutylene glycol dimethacrylate, dodecabutylene glycol dimethacrylate, polybutylene glycol dimethacrylate such as tridecabutylene glycol dimethacrylate, heptaethylene glycol tripropylene glycol diacrylate, nonaethylene glycol propylene glycol Acrylate, tetradecanol ethylene glycol propylene glycol diacrylate, nonaethylene glycol dipropylene glycol diacrylate, tetradecamethylene glycol dipropylene glycol diacrylate, nonaethylene glycol tripropylene glycol diacrylate,
Polyethylene glycol polypropylene glycol diacrylate such as tetradecaethylene glycol tripropylene glycol diacrylate, heptaethylene glycol glycol tripropylene glycol dimethacrylate, nonaethylene glycol propylene glycol dimethacrylate, tetradecaethylene glycol propylene glycol dimethacrylate, nonaethylene glycol dipropylene Polyethylene glycol polypropylene glycol dimethacrylate, such as glycol dimethacrylate, tetradecaethylene glycol dipropylene glycol dimethacrylate, nonaethylene glycol tripropylene glycol dimethacrylate, tetradecaethylene glycol tripropylene glycol dimethacrylate, decaethylene Examples include polyethylene glycol polybutylene glycol diacrylate such as recall pentabutylene glycol diacrylate, polyethylene glycol polybutylene glycol dimethacrylate such as decaethylene glycol pentabutylene glycol dimethacrylate, etc., and these are used alone or in combination of two or more. .

Among the above examples, examples of the alkylene oxide group-containing monomer represented by the general formula (I) include nonamethylene glycol diacrylate and tridecamethylene glycol from the viewpoint of hue and heat resistance. Polymethylene glycol diacrylate such as diacrylate, tetradecamethylene glycol diacrylate, tricosamethylene glycol diacrylate, nonamethylene glycol dimethacrylate, tridecamethylene glycol dimethacrylate, tetradecamethylene glycol dimethacrylate, tricosamethylene glycol dimethacrylate Polymethylene glycol dimethacrylate, nonaethylene glycol diacrylate, tridecaethylene glycol diacrylate, tetradecaethylene glycol diacrylate, etc. Relate, polyethylene glycol diacrylate, such as Trichoderma Sa ethylene glycol diacrylate, nonaethylene glycol dimethacrylate,
Polyethylene glycol dimethacrylate such as tridecaethylene glycol dimethacrylate, tetradecaethylene glycol dimethacrylate and tricosa ethylene glycol dimethacrylate, polypropylene glycol dimethacrylate such as nonapropylene glycol diacrylate, dodecapropylene glycol diacrylate and tridecapropylene glycol diacrylate Polybutylene glycol such as acrylate, nonapropylene glycol dimethacrylate, dodecapropylene glycol dimethacrylate, tridecapropylene glycol dimethacrylate, polypropylene glycol dimethacrylate, nonabutylene glycol diacrylate, dodecabutylene glycol diacrylate, tridecabutylene glycol diacrylate, etc. The Crylate, polybutylene glycol dimethacrylate such as nonabutylene glycol dimethacrylate, dodecabutylene glycol dimethacrylate, tridecabutylene glycol dimethacrylate, heptaethylene glycol chotripropylene glycol diacrylate, nonaethylene glycol propylene glycol diacrylate, tetradecaethylene glycol Polyethylene glycol polypropylene glycol such as propylene glycol diacrylate, nonaethylene glycol dipropylene glycol diacrylate, tetradecaethylene glycol dipropylene glycol diacrylate, nonaethylene glycol tripropylene glycol diacrylate, and tetradecaethylene glycol tripropylene glycol diacrylate Diacrylate, heptaethylene glycol tripropylene glycol dimethacrylate, nonaethylene glycol propylene glycol dimethacrylate, tetradecaethylene glycol propylene glycol dimethacrylate, nonaethylene glycol dipropylene glycol dimethacrylate, tetradecaethylene glycol dipropylene glycol dimethacrylate, Polyethylene glycol polypropylene glycol dimethacrylate such as nonaethylene glycol tripropylene glycol dimethacrylate and tetradecaethylene glycol tripropylene glycol dimethacrylate, polyethylene glycol polybutylene glycol diacrylate such as decaethylene glycol pentabutylene glycol diacrylate,
Polyfunctional monomers such as polyethylene glycol polybutylene glycol dimethacrylate, such as decaethylene glycol pentabutylene glycol dimethacrylate, are preferred.

Among the above-mentioned examples, nonaethylene glycol diacrylate, tridecaethylene glycol diacrylate, tetradecaethylene glycol diacrylate, tricosa ethylene glycol didiene, from the viewpoint of adhesion and dyeability to the organic silane-based hard coat film. Polyethylene glycol diacrylate such as acrylate, nonaethylene glycol dimethacrylate, tridecaethylene glycol dimethacrylate, tetradecaethylene glycol dimethacrylate, tricosa ethylene glycol dimethacrylate, etc. polyethylene glycol dimethacrylate, nonapropylene glycol diacrylate, dodecapropylene glycol Polypropylene glycol diacrylate such as diacrylate and tridecapropylene glycol diacrylate Polyacrylate glycol dimethacrylate such as acrylate, nonapropylene glycol dimethacrylate, dodecapropylene glycol dimethacrylate, tridecapropylene glycol dimethacrylate, heptaethylene glycol tripropylene glycol diacrylate, nonaethylene glycol propylene glycol diacrylate, tetradecaethylene glycol propylene Polyethylene glycol polypropylene such as glycol diacrylate, nonaethylene glycol dipropylene glycol diacrylate, tetradeca ethylene glycol dipropylene glycol diacrylate, nona ethylene glycol tripropylene glycol diacrylate, tetradeca ethylene glycol tripropylene glycol diacrylate, etc. Glycol diacrylate, heptaethylene glycol tripropylene glycol dimethacrylate, nonaethylene glycol propylene glycol dimethacrylate, tetradecaethylene glycol propylene glycol dimethacrylate, nonaethylene glycol dipropylene glycol dimethacrylate, tetradecaethylene glycol dipropylene glycol dimethacrylate , Nonaethylene glycol tripropylene glycol dimethacrylate,
Polyalkylene glycol di (meth) acrylate having 2 to 3 carbon atoms in the alkylene oxide group such as polyethylene glycol polypropylene glycol dimethacrylate such as tetradeca ethylene glycol tripropylene glycol dimethacrylate is particularly preferable.

Among the above-mentioned examples, tetradecaethylene glycol di (meth) acrylate is selected from the viewpoints of balance of hue, strength at the time of punching, dyeability, heat resistance, and adhesiveness to organic silane-based hard coat film. Particularly preferred.

The amount of the alkylene oxide group-containing monomer represented by the general formula (I) used is preferably 1 to 50 parts by weight based on 100 parts by weight of all the monomers. If the amount is less than 1 part by weight, the strength and dyeing property at the time of punching are likely to decrease,
In addition, there is a problem that the adhesiveness to the organic silane-based hard coat film is likely to decrease. If it exceeds 50 parts by weight, there are problems that the heat resistance is likely to be lowered, the hue tends to be yellowish, and the specific gravity is increased.

The monomer containing an alkylene oxide group represented by the general formula (I) has a strength at the time of punching,
In order to sufficiently improve the dyeability and the adhesion to the organic silane-based hard coat film, it is preferable to use 5 parts by weight or more with respect to 100 parts by weight of all the monomers, and to improve heat resistance. It is preferably used in an amount of 30 parts by weight or less based on 100 parts by weight of all the monomers so as not to decrease the color, not give a yellowish hue, and not increase the specific gravity. Similarly, 10 to 30 parts by weight, especially 1
It is preferable to use 0 to 20 parts by weight.

Examples of the polyfunctional (meth) acrylate represented by the above general formula (II) include 2,2-dimethyl-
1,3-propanediol diacrylate, 2-methyl-2-ethyl-1,3-propanediol diacrylate, 2-methyl-2-isopropyl-1,3-propanediol diacrylate, 2-methyl-2-propyl −
1,3-propanediol diacrylate, 2,2-diethyl-1,3-propanediol diacrylate, 2
-Ethyl-2-propyl-1,3-propanediol diacrylate, 2-ethyl-2-isopropyl-1,3
-Propanediol diacrylate, 2-ethyl-2-
Butyl-1,3-propanediol diacrylate,
2,2-dipropyl-1,3-propanediol diacrylate, 2-propyl-2-butyl-1,3-propanediol diacrylate, 2,2-dibutyl-1,3
-Propanediol diacrylate, 2,2-diisopropyl-1,3-propanediol diacrylate, 2
-Propyl-2-isopropyl-1,3-propanediol diacrylate, 2-methyl-2-phenyl-1,
3-propanediol diacrylate, 2-ethyl-2
-Phenyl-1,3-propanediol diacrylate, 2-propyl-2-phenyl-1,3-propanediol diacrylate, 2-isopropyl-2-phenyl-1,3-propanediol diacrylate, 2,2
-Diphenyl-1,3-propanediol diacrylate, 2-methyl-2-cyclopentyl-1,3-propanediol diacrylate, 2-ethyl-2-cyclopentyl-1,3-propanediol diacrylate, 2
-Propyl-2-cyclopentyl-1,3-propanediol diacrylate, 2-isopropyl-2-cyclopentyl-1,3-propanediol diacrylate,
2,2-dicyclopentyl-1,3-propanediol diacrylate, 2-methyl-2-cyclohexyl-
1,3-propanediol diacrylate, 2-ethyl-2-cyclohexyl-1,3-propanediol diacrylate, 2-propyl-2-cyclohexyl-1,
Polyfunctional acrylates such as 3-propanediol diacrylate, 2-isopropyl-2-cyclohexyl-1,3-propanediol diacrylate, 2,2-dicyclohexyl-1,3-propanediol diacrylate, 2,2-dimethyl -1,3-propanediol dimethacrylate, 2-methyl-2-ethyl-1,3-propanediol dimethacrylate, 2-methyl-2-isopropyl-1,3-propanediol dimethacrylate, 2-methyl-2- Propyl-1,3-propanediol dimethacrylate, 2,2-diethyl-1,3-propanediol dimethacrylate, 2-ethyl-2-propyl-1,3-propanediol dimethacrylate,
2-ethyl-2-isopropyl-1,3-propanediol dimethacrylate, 2-ethyl-2-butyl-1,
3-propanediol dimethacrylate, 2,2-dipropyl-1,3-propanediol dimethacrylate,
2-Propyl-2-butyl-1,3-propanediol dimethacrylate, 2,2-dibutyl-1,3-propanediol dimethacrylate, 2,2-diisopropyl-1,3-propanediol dimethacrylate, 2-propyl -2-isopropyl-1,3-propanediol dimethacrylate, 2-methyl-2-phenyl-1,3
-Propanediol dimethacrylate, 2-ethyl-2
-Phenyl-1,3-propanediol dimethacrylate, 2-propyl-2-phenyl-1,3-propanediol dimethacrylate, 2-isopropyl-2-phenyl-1,3-propanediol dimethacrylate,
2,2-diphenyl-1,3-propanediol dimethacrylate, 2-methyl-2-cyclopentyl-1,3
-Propanediol dimethacrylate, 2-ethyl-2
-Cyclopentyl-1,3-propanediol dimethacrylate, 2-propyl-2-cyclopentyl-1,3
-Propanediol dimethacrylate, 2-isopropyl-2-cyclopentyl-1,3-propanediol dimethacrylate, 2,2-dicyclopentyl-1,3-
Propanediol dimethacrylate, 2-methyl-2-
Cyclohexyl-1,3-propanediol dimethacrylate, 2-ethyl-2-cyclohexyl-1,3-propanediol dimethacrylate, 2-propyl-2-
Cyclohexyl-1,3-propanediol dimethacrylate, 2-isopropyl-2-cyclohexyl-1,
Examples thereof include polyfunctional methacrylates such as 3-propanediol dimethacrylate and 2,2-dicyclohexyl-1,3-propanediol dimethacrylate, and these are used alone or in combination of two or more.

As the polyfunctional (meth) acrylate represented by the above general formula (II), among the above-mentioned examples,
From the viewpoint of specific gravity and heat resistance, polyfunctional acrylates such as 2,2-dimethyl-1,3-propanediol diacrylate, 2,2-dimethyl-1,3-propanediol dimethacrylate, and 2-methyl-2- Ethyl-1,3-propanediol dimethacrylate, 2-methyl-2-isopropyl-1,3-propanediol dimethacrylate, 2-methyl-2-propyl-1,3-propanediol dimethacrylate, 2,2-diethyl Polyfunctional methacrylates such as -1,3-propanediol dimethacrylate are preferable, and among them, 2,2-dimethyl-
1,3-Propanediol dimethacrylate is particularly preferred.

Polyfunctionality (meta) represented by the general formula (II)
The amount of the acrylate used is preferably 1 to 50 parts by weight based on 100 parts by weight of all the monomers. If it is less than 1 part by weight, the heat resistance tends to decrease and the specific gravity tends to increase. If it exceeds 50 parts by weight, the strength and dyeing property at the time of punching are likely to be lowered, and the adhesiveness to the organic silane-based hard coat film is likely to be lowered.

Polyfunctionality (meta) represented by the general formula (II)
Acrylate is necessary to improve heat resistance sufficiently.
It is preferable to use 5 parts by weight or more based on 100 parts by weight of all the monomers, and the strength and dyeing property at the time of punching are not deteriorated, and the adhesiveness to the organic silane-based hard coat film is not deteriorated. Thus, it is preferable to use 30 parts by weight or less with respect to 100 parts by weight of all the monomers. Similarly, it is particularly preferable to use 10 to 30 parts by weight based on all the monomers.

Specific examples of the monofunctional monomer among the above-mentioned other copolymerizable vinyl monomers include methyl acrylate, ethyl acrylate, propyl acrylate, n-butyl acrylate and acrylic acid. i-butyl, acrylic acid t
-Butyl, pentyl acrylate, n-hexyl acrylate, 2-ethylhexyl acrylate, n-octyl acrylate, dodecyl acrylate, butoxyethyl acrylate, octadecyl acrylate, phenyl acrylate, benzyl acrylate, naphthyl acrylate, Cyclopentyl acrylate, cyclohexyl acrylate, methyl cyclohexyl acrylate, trimethyl cyclohexyl acrylate, norbornyl acrylate, norbornyl methyl acrylate, isobornyl acrylate, bornyl acrylate, menthyl acrylate, fentyl acrylate, adamantyl acrylate, acrylic Dimethyladamantyl acid, tricyclo acrylate [5.2.1.0 ^2,6 ] deca-8-yl, tricyclo acrylate [5.2.1.0]
^2,6 ] Deca-4-methyl, cyclodecyl acrylate, acrylic acid esters such as glycerin monoacrylate,
Methyl methacrylate, ethyl methacrylate, propyl methacrylate, n-butyl methacrylate, methacrylic acid i
-Butyl, t-butyl methacrylate, pentyl methacrylate, n-hexyl methacrylate, 2-ethylhexyl methacrylate, n-octyl methacrylate, dodecyl methacrylate, butoxyethyl methacrylate, octadecyl methacrylate, phenyl methacrylate, methacrylic acid. Benzyl, naphthyl methacrylate, cyclopentyl methacrylate, cyclohexyl methacrylate, methylcyclohexyl methacrylate, trimethylcyclohexyl methacrylate, norbornyl methacrylate, norbornyl methyl methacrylate, isobornyl methacrylate, bornyl methacrylate, menthyl methacrylate, fentyl methacrylate. , Adamantyl methacrylate, dimethyladamantyl methacrylate, tricyclomethacrylate [5.
2.1.0 ^2,6 ] deca-8-yl, tricyclo [5.2.1.0 ^2,6 ] deca-4-methyl, methacrylic acid cyclodecyl, glycerin monomethacrylate and other methacrylic acid esters, N -Methylmaleimide, N-
Ethylmaleimide, N-propylmaleimide, N-butylmaleimide, N-cyclohexylmaleimide, N-phenylmaleimide, N-methylphenylmaleimide, N
-N-substituted maleimide acrylamides such as chlorophenyl maleimide, N-methoxyphenyl maleimide, N-carboxyphenyl maleimide, etc., methacrylamide, N dimethyl acrylamide, N-diethyl acrylamide, N-dimethyl methacrylamide, N-diethyl methacrylamide, etc. (Meth) acrylamides such as (meth) acrylamides, calcium acrylate, barium acrylate, lead acrylate, tin acrylate, zinc acrylate, calcium methacrylate, barium methacrylate, lead methacrylate, tin methacrylate, zinc methacrylate Acrylic acid metal salts, unsaturated carboxylic acids such as acrylic acid and methacrylic acid, epoxy group-containing vinyl compounds such as glycidyl acrylate and glycidyl methacrylate, hydroxyethyl acrylate, Examples thereof include hydroxyl-containing vinyl compounds such as droxyethyl methacrylate, alkoxysilyl group-containing vinyl compounds such as γ- (methacryloxypropyl) trimethoxysilane, and vinyl cyanide compounds such as acrylonitrile and methacrylonitrile. These are one kind. Or, it is used in two or more kinds.

Specific examples of the polyfunctional monomer among the above-mentioned other copolymerizable vinyl monomers include ethylene glycol diacrylate, glycerin diacrylate, glycerin triacrylate and 1,4-butanediol diacrylate. Acrylate, 1,6-hexanediol diacrylate, 1,9-nonanediol diacrylate, 1,10
-Decanediol diacrylate, 1,12-dodecanediol diacrylate, 1-acryloyl-2-hydroxy-3-acryloylpropane, pentaerythritol tetraacrylate, 1,1,1-trimethylolpropane triacrylate, dipentaerythritol hexaacrylate Acrylic esters such as hexamethylolmelamine hexaacrylate, N, N ′, N ″ -tris (2-acryloyloxyethyl) isocyanurate, ethylene glycol dimethacrylate, glycerin dimethacrylate, glycerin triacrylate,
1,4-butanediol dimethacrylate, 1,6-hexanediol dimethacrylate, 1,9-nonanediol dimethacrylate, 1,10-decanediol dimethacrylate, 1,12-dodecanediol dimethacrylate, 1-methacryloyl-2 -Hydroxy-3-methacryloylpropane, pentaerythritol tetramethacrylate, 1,1,1-trimethylolpropane trimethacrylate, dipentaerythritol hexamethacrylate, hexamethylolmelamine hexamethacrylate, N, N ', N "-tris (2-methacryloyl) Methacrylic acid esters such as oxyethyl) isocyanurate, ethylene glycol bisallyl carbonate, diethylene glycol bisallyl carbonate, triethylene glycol bis Allyl carbonate, tetraethylene glycol bis allyl carbonate, pentaethylene glycol bis allyl carbonate, polypropylene glycol bis allyl carbonate, trimethylene glycol bis allyl carbonate, 3-hydroxypropoxy propanol bis allyl carbonate, glycerin bis allyl carbonate, triglycerin bis allyl carbonate, Diallyl carbonate, diarylidene pentaerythritol, triarylidene sorbitol, diarylidene-2,2,6,6-tetramethylol cyclohexanone, trimethylolene hexamethylol melamine, diarylidene-D-glucose, bisphenol A diallyl ether, bisphenol S diallyl ether , Ethylene glycol diallyl ether, 1 1,1-trimethylolpropane triallyl ether, neopentyl glycol triallyl ether, allyl acrylate, methallyl acrylate, vinyl acrylate, allyl methacrylate, methallyl methacrylate, vinyl methacrylate, diallyl phthalate (diallyl orthophthalate, diallyl isophthalate, diallyl) Examples thereof include terephthalate and a mixture of two or more thereof, allyl compounds such as triallyl isocyanurate and allylidene compounds, and divinylbenzene. These are used alone or in combination of two or more.

Among the above-mentioned other copolymerizable vinyl-based monomers, methacrylic monomer is a monofunctional monomer in terms of hue, strength at the time of punching, specific gravity, transparency and heat resistance. Methyl acid, ethyl methacrylate, propyl methacrylate, n-butyl methacrylate, i-butyl methacrylate, t-butyl methacrylate, pentyl methacrylate,
N-hexyl methacrylate, 2-ethylhexyl methacrylate, n-octyl methacrylate, butoxyethyl methacrylate, phenyl methacrylate, benzyl methacrylate, naphthyl methacrylate, alicyclic hydrocarbon having 5 to 22 carbon atoms in the ester portion. Methacrylic acid esters such as methacrylic acid having a group, aromatic vinyl compounds such as styrene, hydroxyl group-containing vinyl compounds such as hydroxyethyl methacrylate, and alkoxysilyl group-containing vinyl compounds such as γ- (methacryloxypropyl) trimethoxysilane. Is preferred, and as the polyfunctional monomer,
Linear alkylene glycol diacrylates such as ethylene glycol diacrylate, 1,4-butanediol diacrylate and 1,6-hexanediol diacrylate, allyl methacrylate, methallyl methacrylate,
Linear alkylene glycol dimethacrylates such as ethylene glycol dimethacrylate, 1,4-butanediol dimethacrylate, and 1,6-hexanediol dimethacrylate are preferred.

The composition of the monomer for producing the above plastic lens is 1 to 50 parts by weight (particularly 10 to 20 parts by weight) of the monomer containing the alkylene oxide group represented by the general formula (I). ), 1 to 50 parts by weight of a polyfunctional (meth) acrylate represented by the general formula (II) (particularly 10
-30 parts by weight), styrene 15-60 parts by weight (particularly 30 parts by weight)
.About.50 parts by weight) and other copolymerizable vinyl monomers 0
It is preferable to add -60 parts by weight (particularly 0-30 parts by weight) so that the total amount is 100 parts by weight.

If the amount of styrene used is small, it tends to be difficult to increase the refractive index (particularly to make the refractive index 1.54 or more). When the amount of styrene used is large, it becomes difficult to achieve an optically low dispersion, and it becomes difficult to set the Abbe number to 35 or more, and the hue tends to be yellowish.

In the above, when the amount of the other copolymerizable vinyl-based monomer used is large, it becomes difficult to keep the refractive index large (particularly to keep the refractive index of 1.54 or more), and the specific gravity is also increased. Should be kept small (especially if the specific gravity is 1.1
It is difficult to keep it below 5).

A hydroxyl group-containing vinyl compound and an alkoxysilyl group-containing vinyl compound, which are one of other copolymerizable vinyl-based monomers, are used in an amount of 0.01 based on 100 parts by weight of all monomers.
It is preferable to use more than parts by weight in order to obtain the effect of improving the adhesiveness to the organic silane-based hard coat film.

The plastic lens obtained by the above-mentioned method for producing a plastic lens has a phosphite-based, phenol-based, thioether-based antioxidant or the like in view of deterioration prevention, thermal stability, processability and the like. , Aliphatic alcohols, fatty acid esters, phthalic acid esters, triglycerides, fluorochemical surfactants,
Release agents such as higher fatty acid metal salts, other lubricants, plasticizers,
You may add and use an antistatic agent, a ultraviolet absorber, a flame retardant, a heavy metal deactivator, etc. These are preferably added at the time of polymerization.

On the surface of the plastic lens obtained by the above-mentioned method for producing a plastic lens, MgF ₂ ,
An inorganic compound such as SiO ₂ is coated by a vacuum deposition method, a sputtering method, an ion plating method, or the like, an organic silicon compound such as a silane coupling agent, a vinyl monomer, a melamine resin, an epoxy resin, a fluorine resin, or the like on the lens surface. By hard-coating a silicone resin or the like, it is possible to improve moisture resistance, optical characteristics, chemical resistance, abrasion resistance, antifog, and the like.

An organic silane-based hard coat film and a cured film of an organic silane resin can be directly laminated on the surface of the plastic lens obtained by the above-mentioned method for producing a plastic lens.

The above-mentioned organic silane resin is, for example, a compound represented by the chemical formula 5 [general formula (III)]

Embedded image R ⁸ R ⁹ _a Si (OR ¹⁰ ) _3-a (III) (wherein R ⁸ is an organic group containing an epoxy group having 2 to ⁸ carbon atoms, and R ⁹ is 1 to 6 carbon atoms). , An alkyl group, an alkenyl group, a halogenated alkyl group or an allyl group, R ¹⁰ is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxyalkyl group or an acyl group, and a is an integer of 0 to 2). The indicated organosilane compound or its partial hydrolyzate. More specific examples are γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, γ-glycidoxypropyltris (methoxyethoxy) silane, γ-glycidoxypropylmethyldimethoxysilane, γ -Organic silane compounds such as glycidoxypropylmethyldiethoxysilane or partial hydrolysates thereof. Examples of commercially available products include KP64C (trade name of Shin-Etsu Chemical Co., Ltd.).

10 to 80% by weight of a colloidal solution prepared by dispersing the above organic silane resin and inorganic fine particles such as antimony oxide sol, silica sol, titania sol and alumina sol in water or alcohol such as methanol, ethanol, isobutanol and diacetone alcohol. % Is added directly to the surface of the plastic lens obtained by the above-mentioned method for producing a plastic lens, and the composition is hardened by heating at 50 to 140 ° C. to form a hard coat layer. At this time, if necessary, a primer layer may be provided between the plastic lens surface and the hard coat layer, or the hard coat layer may be provided after the plastic lens substrate surface is subjected to surface treatment such as plasma treatment. The plastic lens obtained by the method for producing a plastic lens described above does not require these pretreatments.

The above-mentioned inorganic fine particles preferably have a particle diameter of 1 to 100 μm, and a commercially available colloidal solution dispersed in a water or organic solvent can also be used.

If necessary, the organic silane resin may include a perchlorate such as aluminum chelate, perchloric acid, ammonium perchlorate and aluminum perchlorate, and an alkali metal such as sodium acetate or potassium propionate. Curing catalysts such as salts and quaternary ammonium salts such as tetramethylammonium hydroxide can also be used.

The plastic lens obtained by the above-mentioned method for producing a plastic lens can be dyed by immersing it in water in which a dye is dispersed.

As the dye, those generally used in the art can be used as they are. For example, C.I. I.
Disperse Red 13, 56, 112, C.I. I. Disperse Yellow 3, 7, 31, 42, 54, 198,
C. I. Disperse Blue 1, 3, 5, 54, 56,
197 etc.

In the above dyeing, a pH adjusting agent, a wetting agent,
By adding a dyeing aid such as a surfactant, a dispersion accelerator, or an antifoaming agent, it is possible to improve the dyeing strength and dyeing uniformity.

At the time of the above dyeing, benzyl alcohol,
Addition of aromatic compounds such as phenol, butyl benzoate and methyl salicylate, aliphatic alcohols such as 1-butanol, ethyl cellosolve and cyclopentanol, organic compounds such as butyl cellosolve acetate and aliphatic ester such as methyl acetoacetate as a carrier. Thereby, the density of dyeing can be improved.

[0076]

EXAMPLES The present invention will be described below in greater detail by giving Examples, but the scope of the present invention is not limited thereto.

In the method for producing a plastic lens according to the present invention, 400 nm when 1 part by weight of the gasket material is immersed in 5 parts by weight of the polymerizable monomer at 40 ° C. for 6 hours.
When measuring the degree of decrease (%) in the light transmittance of the polymerizable monomer, the following method was applied. Further, hereinafter, the term “degree of decrease in light transmittance (%)” indicates the degree of decrease in light transmittance of a polymerizable monomer (%) measured according to the following method.・ 20g of 1.0g pellets of each gasket material
Put in a sample tube, add 5.0g of polymerizable monomer and 40 ℃
Let stand and soak for 6 hours. Then, after removing the pellets from the polymerizable monomer by filtration, the light transmittance of the polymerizable monomer at 400 nm is measured by a spectrophotometer (manufactured by Shimadzu Corporation).
Was measured by At this time, a quartz glass cell having an optical path length of 10 mm was used, and the light transmittance was set to 100% with air as a reference. The degree of decrease in the light transmittance of the polymerizable monomer (%) is calculated from the light transmittance (%) of the polymerizable monomer before immersion of the gasket material to the light transmittance (%) of the polymerizable monomer after immersion of the gasket material. %).

Examples 1 to 7 Gasket materials shown in Table 1 were injection molded into gasket shapes. Next, through this gasket, fix the two glass plates with lens-like irregularities with clips with springs,
The casting mold was assembled. Next, 41 parts by weight of styrene, 24 parts by weight of tricyclo [5.2.1.02,6] deca-8-yl methacrylate, 2,2-dimethyl-1,3-
20 parts by weight of propanediol dimethacrylate, 15 parts by weight of tetradecaethylene glycol dimethacrylate,
Diisopropyl peroxydicarbonate (10 hours half-life temperature: 40.5 ° C.) as a polymerization initiator in a polymerizable monomer composed of 1.0 part by weight of a dimer of α-methylstyrene
1.0 part by weight, t-butylperoxy (2-ethylhexanoate) (10-hour half-life temperature: 72.5 ° C.)
After adding 5 parts by weight and stirring thoroughly, the mixture was poured into the above casting mold, held at 25 ° C for 6 hours, and then heated to 80 ° C over 17 hours. The cured lens was removed from the mold, heat-treated at 120 ° C. for 2 hours, and then cooled to room temperature.

Comparative Examples 1 to 5 Gasket materials shown in Table 2 were injection molded into gasket shapes. Next, through this gasket, fix the two glass plates with lens-like irregularities with clips with springs,
The casting mold was assembled. Next, 41 parts by weight of styrene, 24 parts by weight of tricyclo [5.2.1.0 ^2,6 ] deca-8-yl methacrylate, 2,2-dimethyl-1,3-
20 parts by weight of propanediol dimethacrylate, 15 parts by weight of tetradecaethylene glycol dimethacrylate,
Diisopropyl peroxydicarbonate (10 hours half-life temperature: 40.5 ° C.) as a polymerization initiator in a polymerizable monomer composed of 1.0 part by weight of a dimer of α-methylstyrene
1.0 part by weight, t-butylperoxy (2-ethylhexanoate) (10-hour half-life temperature: 72.5 ° C.)
After adding 5 parts by weight and stirring thoroughly, the mixture was poured into the above casting mold, held at 25 ° C for 6 hours, and then heated to 80 ° C over 17 hours. The cured lens was removed from the mold, heat-treated at 120 ° C. for 2 hours, and then cooled to room temperature.

In Examples 1 to 7 and Comparative Examples 1 to 5,
The injection moldability when each gasket material is injection molded into a gasket shape, the heat resistance of the gasket when cast polymerized using each gasket, the cloudiness of the obtained lens due to the erosion of the gasket, the cast moldability, etc. The results are shown in Tables 3 and 4.

Examples 8 to 12 A glass plate having two lens-like irregularities is clipped with a spring through a gasket made of Tuffuma-A20090 (ethylene-α olefin copolymer, manufactured by Mitsui Petrochemical Co., Ltd.). It was fixed and the casting mold was assembled. next,
41 parts by weight of styrene, tricyclomethacrylate [5.
2.1.02,6] Deca-8-yl 24 parts by weight, 2,2-
Dimethyl-1,3-propanediol dimethacrylate 20 parts by weight, tetradecaethylene glycol dimethacrylate 15 parts by weight, α-methylstyrene dimer 1.0
The polymerization initiator shown in Table 5 was added to the polymerizable monomer consisting of parts by weight and sufficiently stirred, and then the mixture was poured into the above casting mold and cast polymerization was carried out at the polymerization temperature shown in Table 5. . The lens after cast polymerization was removed from the mold, heat-treated at 120 ° C. for 2 hours, and then cooled to room temperature.

In Examples 8 to 12, the heat resistance of the gasket after cast polymerization, the cloudiness of the obtained lens due to the erosion of the gasket, the cast moldability, etc. were examined and shown in Table 6. Two
Used in seeds and above.

Examples 13 to 23 Tahuma-A20090
Two glass plates having lens-shaped irregularities were fixed with a clip with a spring through a gasket made of (ethylene-α-olefin copolymer, manufactured by Mitsui Petrochemical Co., Ltd.),
The casting mold was assembled. Next, in the polymerizable monomer having the composition shown in Table 7, 1.0 part by weight of diisopropyl peroxydicarbonate (10-hour half-life temperature: 40.5 ° C.) as a polymerization initiator, t -Butyl peroxy (2-ethylhexanoate) (10-hour half-life temperature: 72.5 ° C) 0.5 part by weight was added and sufficiently stirred, and then poured into the above casting mold, and the temperature was 25 ° C. The temperature was maintained for 6 hours and then raised to 80 ° C. over 17 hours. The cured lens is removed from the mold, heat-treated at 120 ° C. for 2 hours, cooled to room temperature, dipping coated with an organic silane-based hard coating agent (trade name “KP64C”, Shin-Etsu Chemical Co., Ltd.), and kept at room temperature for 30 minutes. 90 ° C for 30 minutes, 120 ° C for 1
Heat cured for hours.

The refractive index, Abbe number, specific gravity, heat resistance, punching tensile strength, hue, hard coat adhesion, dyeability, cloudiness due to gasket erosion, etc. of the lenses obtained in Examples 13 to 23 were examined, and Table 8 was obtained. It was shown to.

Examples 24-39 Tahuma-A20090
Two glass plates having lens-shaped irregularities were fixed with a clip with a spring through a gasket made of (ethylene-α-olefin copolymer, manufactured by Mitsui Petrochemical Co., Ltd.),
The casting mold was assembled. Next, the polymerizable monomer having the composition shown in Table 9 was added to the polymerizable monomer as a polymerization initiator in an amount of 1.0 part by weight of diisopropyl peroxydicarbonate (10-hour half-life temperature: 40.5 ° C.), t -Butyl peroxy (2-ethylhexanoate) (10-hour half-life temperature: 72.5 ° C) 0.5 part by weight was added and sufficiently stirred, and then poured into the above casting mold, and the temperature was 25 ° C. The temperature was maintained at 80 ° C for 6 hours and then raised to 80 ° C over 17 hours. The cured lens is removed from the mold, heat-treated at 120 ° C. for 2 hours, cooled to room temperature, dipping coated with an organic silane-based hard coating agent (trade name “KP64C”, Shin-Etsu Chemical Co., Ltd.), and kept at room temperature for 30 minutes. 90 ° C for 30 minutes, 120 ° C for 1
Heat cured for hours.

The refractive index, Abbe number, specific gravity, heat resistance, punching tensile strength, hue, hard coat adhesion, dyeability, cloudiness due to gasket erosion, etc. of the lenses obtained in Examples 24 to 39 were examined, and Table 10 is shown. It was shown to.

The characteristic evaluation was based on the following methods. -Injection moldability: The moldability of each gasket material when injection-molded into a gasket shape was evaluated. Evaluation: ◯ is easy to mold Δ is difficult to mold × is difficult to mold ・ Gasket heat resistance: Casting polymerization was performed using each gasket, and the shape of the gasket at the time of completion of polymerization was evaluated. Evaluation: ○ indicates that the shape of the gasket is maintained. In the case of ×, the gasket melts and loses its shape. Gasket erosion: Visual observation was performed in a dark room under strong light irradiation of a 150-watt slide projector (CABIN manufactured by Cabin Industry Co., Ltd.), and the degree of cloudiness due to erosion was evaluated on a scale of five. (Evaluation) ◎: Especially transparent, ○: Transparent, Δ: Slightly cloudy,
X: Cloudy XX: Large cloudy-Lens cast moldability: Cast molding of each lens was evaluated by casting polymerization using each gasket. Evaluation: ○: Good castability. △: sink mark or liquid leakage sometimes occurs on the lens surface. ×: sink mark or liquid leakage occurs on the lens surface. ・ Refractive index, Abbe number: Abbe refractometer (Atago Co. Manufactured by K.K.) and measured at 20 ° C. The values in the table are for the D line (58
Value at 9.3 nm). -Specific gravity: Measured by the water substitution method. -Heat resistance: TMA (Thermal Mechanical Anallyzer, manufactured by Seiko Denshi) was used to measure the Tg (softening temperature) and the penetration amount (thermal deformation amount). -Pulling tensile strength: A 2.0 mm diameter hole was opened at both ends of a lens having a thickness of 2 mm, a screw was inserted, and this screw was pulled by a tensile tester to measure the strength. Hue: YI value (yellowness) was measured using a color difference meter (manufactured by Nippon Denshoku).・ Hard coat adhesion: 1m with a knife on the hard coat film
After inserting 11 crosswise grids, 11 each in length and width, and adhering cellophane tape (made by Nichiban), the cellophane tape was rapidly peeled off and the number of squares which were not peeled off was examined. Evaluation: ◯ is 100/100. X is 0/100. Dyeability: 5 g of the dye, 2 ml of the dispersion aid, and 10 g of benzyl methacrylate were dissolved in 1 l of pure water, the temperature was raised to 90 ° C., and the lens was immersed for 15 minutes for dyeing. The degree of dyeing of the lens after dyeing was evaluated on a five-point scale. Evaluation: 5; It dyes very well. 4; dyes well 3; dyes to some extent 2; dyes slightly 1; dyes little

In the following, A4090 is Toughma-A4
090 (ethylene-α olefin copolymer, manufactured by Mitsui Petrochemical Co., Ltd.), A20090 is Tuffma-A20090
(Ethylene-α olefin copolymer, manufactured by Mitsui Petrochemical Co., Ltd.), A4085 is Tuffuma-A4085 (ethylene-α olefin copolymer, manufactured by Mitsui Petrochemical Co., Ltd.),
LLDP1 and LLDP2 are ethylene-α olefin copolymer (manufactured by Mitsui Petrochemical Co., Ltd.), EUL730 and EUL.
430 is an ethylene-α-olefin copolymer (manufactured by Sumitomo Chemical Co., Ltd.), DPDJ is DPDJ9169 (ethylene-ethyl acrylate-based elastomer, manufactured by Nippon Unicar Co., Ltd.), P22M is miractolane P22M (polyurethane-based elastomer, Nippon Miractolan). Manufactured by)
H4047 represents Hytrel 4047 (polyester elastomer, manufactured by Toray DuPont Co., Ltd.). IPP is diisopropyl peroxydicarbonate (10-hour half-life temperature: 40.5 ° C.), V-70 is 2,2′-azobis (4-methoxy-2,4-dimethylvaleronitrile).
(10-hour half-life temperature: 30 ° C.), PBO is t-butylperoxy (2-ethylhexanoate) (10-hour half-life temperature: 72.5 ° C.), ST is styrene, MMA is methyl methacrylate, TCDMA. Is tricyclo [5.2.1.0 ^2,6 ] deca-8-yl, NPDM is 2,2-dimethyl-1,3-propanediol dimethacrylate, EGDM is ethylene glycol dimethacrylate, and 4EGDM is tetraethylene. Glycol dimethacrylate, DDDM is 1,10-decanediol dimethacrylate, 14EGDM is tetradecaethylene glycol dimethacrylate, and NPDA is 2,2-dimethyl-.
1,3-propanediol diacrylate, 9EGDM
Is nonaethylene glycol dimethacrylate, 9 EGM
M is nonaethylene glycol monomethacrylate, HE
MA is 2-hydroxyethyl methacrylate, α-MS
D is a dimer of α-methylstyrene, and NOM is n-octyl mercaptan. The amounts of α-MSD and NOM used are shown in weight% based on the total amount of monomers.

[0089]

[Table 1] ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Table 1 Physical properties of gasket material ━━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Material Name Density △ H * Light transmittance MFR ** (g / cm3) ( J / g) Degradation (%) (g / 10min) ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Example 1 ethylene-α olefin A4090 0.89 trace 0.1 4 copolymer 〃 2 ethylene-α olefin A20090 0.89 trace 0.1 18 copolymer 〃 3 ethylene-α olefin A4085 0.88 trace 0.1 4 copolymer 〃 4 ethylene-α olefin A4090 / A20090 0.89 trace 0.1 10 copolymer = 50/50 blend 〃 5 ethylene-α olefin LLDPE1 0.92 44 0.1 1 copolymer 〃 6 ethylene-α olefin LLDPE2 0.92 40 0.1 10 copolymer 〃 7 ethylene-α olefin A20090 / L LDPE2 0.89 3 0.1 12 Copolymer = 90/10 blend ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ * DSC heat of fusion above 100 ℃ (JIS-K7122) ** ASTM, D1238, E

[0090]

[Table 2] ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Table 2 Physical properties of gasket material ━━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Material Name Density △ H * Light transmittance MFR ** (g / cm3) ( J / g) Degradation (%) (g / 10min) ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Comparative Example 1 Ethylene-α olefin EUL730 0.89 11 6.5 10 Copolymer 〃 2 Ethylene-α olefin EUL430 0.89 11 6.8 4 Copolymer 〃 3 Ethylene-ethyl acrylate DPDJ--5.1 20 Elastomer 〃 4 Polyurethane P22M--0.2 -Elastomer 5 Polyester H4047--0.6-Elastomer ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ * DSC Heat of fusion of 100 ° C or more (JIS- K7122) ** ASTM, D1238, E

[0091]

[Table 3] ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Table 3 Evaluation results ━━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Gasket evaluation Lens evaluation ━━━━━━━━━━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Injection molding Heat resistance Gasket erosion Casting moldability ━━━━━━━━━━━━━━━ ━━━━━━━━━━━━━━━━━━━━━ Example 1 △ ○ ◎ ○ 〃 2 ○ ○ ◎ ○ 〃 3 △ ○ ◎ ○ 〃 4 ○ ○ ◎ ○ 〃 5 × ○ ◎ × 〃 6 ○ ○ ◎ × 〃 7 ○ ○ ◎ ○ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

[0092]

[Table 4] ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Table 4 Evaluation results ━━━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Gasket evaluation Lens evaluation ━━━━━━━━━━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Injection molding Heat resistance Gasket erosion Casting moldability ━━━━━━━━━━━━━━━ ━━━━━━━━━━━━━━━━━━━━━ Comparative example 1 ○ ○ × × △ 〃 2 △ ○ × × △ 〃 3 ○ ○ × △ 〃 4 × ○ △ △ 〃 5 △ ○ × △ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

[0093]

[Table 5] ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Table 5 Note molding conditions ━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Gasket Polymerization initiator Casting polymerization temperature Name IPP V-70 PBO ━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Example 8 A20090 1.0- Temperature rise to 80 ℃ over 17 hours 〃 9 〃--0.5 〃 〃 10 〃--1.0 〃 〃 11 〃-1.0 0.5 〃 〃 12 〃 1.0-0.5 6 hours after holding at 25 ℃ Temperature rise over ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

[0094]

[Table 6] ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Table 6 Evaluation results ━━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Gasket evaluation Lens evaluation ━━━━━━━━━━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Heat resistance Gasket erosion Casting moldability ━━━━━━━━━━━━━━━━━━ ━━━━━━━━━━━━━━━━━━ Example 8 ○ ◎ ○ 〃 9 ○ ○ ○ 〃 10 ○ ○ ○ 〃 11 ○ ◎ × * 〃 12 × ◎ ○ ━━━━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ * Bubbles and cracks were generated inside the lens.

[0095]

[Table 7] ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Table 7 Mixed liquid composition ━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ ━ ━ ━ ━ ━ ━ 4EGDM DDDM 14EGDM (% by weight) ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Example 13 50 30-- 20---1.0 〃 14 50-30-20---1.0 〃 15 50-30 20----1.0 〃 16 50-30---20-1.0 〃 17 50-30----20 1.0 〃 18 50 15--20--15 1.0 〃 19 50 15----20 15 1.0 〃 20 50-15-20--15 1.0 〃 21 50-15---20 15 1.0 〃 22 50-15 20- -15-1.0 〃 23 50-15 20-15--1.0 ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ ━

[0096]

[Table 8] ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Table 8 Evaluation results ━━━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Refractive index Abbe number Specific gravity Tg Penetration amount Strength YI value Heart coat Dyeing erosion ( −) (−) (G / cm3) (℃) (μm) (kgf) (%) Adhesion (1-5) ━━━━━━━━━━━━━━━━━━━━━ ━━━━━━━━━━━━━━━ Example 13 1.55 41 1.15 147 5 5 1.3 × 1 ◎ 〃 14 1.55 41 1.13 148 5 5 1.3 × 1 ◎ 〃 15 1.55 41 1.09 127 20 5 1.2 × 1 ◎ 〃 16 1.55 41 1.11 86 32 5 1.2 × 5 * ◎ 〃 17 1.55 41 1.13 88 48 20 1.3 ○ 5 * ◎ 〃 18 1.55 41 1.16 137 1 15 1.3 ○ 2 ◎ 〃 19 1.55 41 1.13 68 16 12 1.3 ○ 5 * ◎ 〃 20 1.55 41 1.16 137 1 20 1.3 ○ 3 ◎ 〃 21 1.55 41 1.13 62 17 12 1.3 ○ 5 * ◎ 〃 22 1.55 41 1.10 113 1 5 1.1 × 1 ◎ 〃 23 1.55 41 1.11 131 1 5 1.3 ○ 1 ◎ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ * The lens was deformed during dyeing.

[0097]

[Table 9] ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Table 9 Mixed liquid composition ━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Monomer composition (weight part) α-MSD ST MMA TCDMA NPDM NPDA 9EGDM 14EGDM 9EGMM HEMA (wt%) ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Example 24 50 15- 20-15---1.0 〃 25 50 15-20--15--1.0 〃 26 50 15--20 15---1.0 〃 27 50 15--20-15--1.0 〃 28 50-15 20- 15---1.0 〃 29 50-15 20--15--1.0 〃 30 50-15-20 15---1.0 〃 31 50-15-20-15--1.0 〃 32 50-15 20--15 --NOM1.0 〃 33 50-15 20--15---〃 34 50-14 20--15-1.0 1.0 〃 35 41 24-20-15---1.0 〃 36 41 24-20--15 --1.0 〃 37 41-24 20-15---1.0 〃 38 41-24 20--15--1.0 〃 39 50 15 20---15-1.0 ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

[0098]

[Table 10] ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Table 10 Evaluation results ━━━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Refractive index Abbe number Specific gravity Tg Penetration amount Strength YI value Heart coat Dyeing erosion ( −) (−) (G / cm3) (℃) (μm) (kgf) (%) Adhesion (1-5) ━━━━━━━━━━━━━━━━━━━━━ ━━━━━━━━━━━━━━━ Example 24 1.55 41 1.11 121 1 15 1.2 ○ 3 ◎ 〃 25 1.55 41 1.11 116 1 20 1.1 ○ 5 ◎ 〃 26 1.55 41 1.11 109 2 15 1.2 ○ 4 ◎ 〃 27 1.55 41 1.11 106 3 20 1.1 ○ 5 ◎ 〃 28 1.55 41 1.10 122 1 15 1.2 ○ 3 ◎ 〃 29 1.55 41 1.10 117 1 20 1.1 ○ 5 ◎ 〃 30 1.55 41 1.10 110 2 15 1.2 ○ 4 ◎ 〃 31 1.55 41 1.10 106 3 20 1.1 ○ 5 ◎ 〃 32 1.55 41 1.10 117 1 20 1.3 ○ 5 ◎ 〃 33 1.55 41 1.10 120 1 20 1.3 ○ 5 ○ 〃 34 1.55 41 1.10 120 1 20 1 .1 ○ 5 ◎ 〃 35 1.55 42 1.12 122 1 15 1.2 ○ 3 ◎ 〃 36 1.55 42 1.12 116 1 20 1.1 ○ 5 ◎ 〃 37 1.55 42 1.11 123 1 15 1.1 ○ 3 ◎ 〃 38 1.55 42 1.11 119 1 20 1.0 ○ 5 ◎ 〃 39 1.55 41 1.10 110 25 12 1.3 ○ 5 ◎ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ ━

[0099]

According to the method of claim 1, the plastic lens obtained by this method is excellent in transparency without clouding or coloring. The method according to claim 2 has excellent castability. According to the method of claim 3, the plastic lens obtained by the method is free from clouding and coloring, is excellent in transparency, and is excellent in castability. The method of claim 4 has the effects of claims 1 to 3 and is particularly excellent in castability. According to the method of claim 5, claim 1
The effects of 4 to 4 are obtained, and the productivity is excellent. The method of claim 6 has the effects of claims 1 to 5, and is particularly excellent in castability. The method according to claim 7 has the effect of the plastic lens according to claims 1 to 6, and is excellent in transparency without clouding or coloring.
According to the method of claim 8, the effects of claims 1 to 7 are obtained, and the high refractive index is excellent. The method according to claim 9 has the effects of claims 1 to 8 and is excellent in transparency, strength at the time of punching, and dyeability.
Since the specific gravity is low and the adhesiveness to the organic silane resin is excellent, the cured film of the organic silane resin (organic silane-based hard coat film) can be directly coated.

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Claims (9)

[Claims] 1. A method for injecting a polymerizable monomer into a plastic lens casting mold sealed with a gasket and performing cast polymerization to produce a plastic lens, with respect to 5 parts by weight of the polymerizable monomer. Using a gasket composed of an ethylene-α-olefin copolymer having a degree of decrease in the light transmittance of the polymerizable monomer at 400 nm of 0.5% or less when 1 part by weight is immersed at 40 ° C for 6 hours. A method of manufacturing a plastic lens, which is characterized by: 2. When manufacturing a plastic lens by injecting a polymerizable monomer into a plastic lens casting mold that is sealed with a gasket and performing a casting polymerization to produce a plastic lens, 100 ° C. by a differential scanning calorimeter (DSC). A method for producing a plastic lens, which comprises using a gasket made of an ethylene-α-olefin copolymer having a heat of fusion of less than 10 Joules / g. 3. When producing a plastic lens by injecting a polymerizable monomer into a plastic lens casting mold that is sealed with a gasket and producing a plastic lens, 5 parts by weight of the polymerizable monomer is used. And the degree of decrease in the light transmittance of the polymerizable monomer at 400 nm (%) is 0.5% or less when 1 part by weight is immersed at 40 ° C. for 6 hours, and the differential scanning calorimeter (DSC) is used. The heat of fusion above 100 ℃ is 1
A method for producing a plastic lens, which comprises using a gasket made of an ethylene-α-olefin copolymer having an amount of less than 0 joule / g. 4. The method for producing a plastic lens according to claim 1, wherein the density of the ethylene-α-olefin copolymer is 0.85 to 0.91 g / cm ³ . 5. The production of a plastic lens according to claim 1, claim 2, claim 3 or claim 4, wherein the ethylene-α-olefin copolymer has a melt flow rate (MFR) of 3 to 100 g / 10 minutes. Law. 6. The method according to claim 1, wherein the casting polymerization is carried out in the range of 10 to 100 ° C., and after the completion of the polymerization, the plastic lens is released from the casting mold. The method for producing a plastic lens according to claim 4 or 5. 7. 1 to 100 parts by weight of the polymerizable monomer
0.01 to 10 parts by weight of a polymerization initiator containing at least one organic peroxide having a 0-hour half-life temperature of 20 to 60 ° C. is blended. Item 5. A method for producing a plastic lens according to item 5 or claim 6. 8. The polymerizable monomer is a monomer mixture containing at least one aromatic monomer, claim 1, claim 2, claim 3, claim 4, claim 5, claim 5. Item 6. A method for producing a plastic lens according to item 6 or 7. 9. The polymerizable monomer is 1 to 50 parts by weight of an alkylene oxide group-containing monomer represented by the general formula (I), and a polyfunctional (meta) represented by the general formula (II). ) 1 to 50 parts by weight of acrylate, 15 to 60 parts by weight of styrene, and 0 to 60 parts by weight of another copolymerizable vinyl monomer so that the total amount thereof is 100 parts by weight. A method for manufacturing a plastic lens according to claim 1, claim 2, claim 3, claim 4, claim 5, claim 6, claim 7 or claim 8. Embedded image R ¹ —O— (R ² O) m —R ³ (I) (wherein R ¹ is an acryloyl group or a methacryloyl group, and R ² is an alkylene group having 1 to 40 carbon atoms) And R ³ is hydrogen, an acryloyl group, a methacryloyl group or a monovalent hydrocarbon group having 1 to 40 carbon atoms other than these, and m is an integer of 9 to 50) (However, R ⁴ and R ⁵ are each independently an acryloyl group,
Or a methacryloyl group, and R ⁶ and R ⁷ are each independently a monovalent hydrocarbon group having 1 to 6 carbon atoms)