JPH08302336A - Gasket for production of plastic lens, production of plastic lens, and plastic lens - Google Patents

Abstract

PURPOSE: To obtain a gasket for the production of plastic lens, excellent in the resistance to the attack by a polymerizable monomer. CONSTITUTION: This gasket is one, made from a mixture comprising 10-100wt.% ethylene/α-olefin copolymer produced by using a metallocene catalyst and 90-0wt.% ethylene/α-olefin copolymer produced by using a catalyst other than the metallocene catalyst. By using this gasket, a plastic lens having a high refractive index, a good balance among hue, strength in boring and a specific gravity and being capable of directly coatable with a cured film of an organosilane resin (hard-coat organosilane film) can be produced.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a gasket for producing a plastic lens, a method for producing a plastic lens and 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 obtained lens is liable to be clouded. 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 by a differential scanning calorimeter (DSC) is 100 ° C.
Above, a gasket made of an ethylene-α-olefin copolymer resin having a heat of fusion of 110 ° C. or higher by DSC of 10 Joule / g or higher has been proposed.
This gasket is intended to improve the heat resistance of the gasket when the polymerizable monomer is cast-polymerized at a high temperature of 100 to 130 ° C., and is inferior in erosion resistance to the aromatic monomer. 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.

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 adhesion 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.

[0013]

As described above, a gasket for producing a plastic lens excellent in erosion resistance against a polymerizable monomer, a high refractive index, a hue and a hole forming process using the gasket have been heretofore used. There is no plastic lens manufacturing method or plastic lens that has a good balance of strength and specific gravity and that can be directly coated with a cured film of an organic silane resin (organic silane-based hard coat film).

An object of the present invention is to provide a gasket for producing a plastic lens which is excellent in erosion resistance against a polymerizable monomer, a method for producing a plastic lens using the gasket, and a plastic lens. Using the above gasket for plastic lens production, it has a high refractive index and a good balance of hue, strength when drilling, and specific gravity. Furthermore, a cured film of an organic silane resin (organic silane hard coat film) A method of manufacturing a plastic lens that can be coated and a plastic lens are provided.

[0015]

[MEANS FOR SOLVING THE PROBLEMS] The gasket for producing a plastic lens in the present invention comprises an ethylene-α-olefin copolymer 10 to 10 polymerized using a metallocene catalyst.
90 to 0% by weight of an ethylene-α-olefin copolymer polymerized by using 100% by weight and a catalyst other than a metallocene catalyst
It is characterized by comprising a mixture of.

In the method for producing a plastic lens according to the present invention, a polymerizable monomer is injected into a plastic lens casting mold which is sealed with a gasket, and when casting is performed to produce a plastic lens, a metallocene catalyst is used. 10-100% by weight of the ethylene-α-olefin copolymer polymerized by using the ethylene-α-olefin copolymer 90-0 polymerized by using a catalyst other than the metallocene catalyst
It is characterized by using a gasket composed of a mixture of wt%.

In the plastic lens of the present invention, a metallocene catalyst is used when a plastic lens is produced by injecting a polymerizable monomer into a plastic lens casting mold which is sealed with a gasket and casting polymerization is carried out. Polymerized ethylene-α-olefin copolymer 10
90 to 0% by weight of an ethylene-α-olefin copolymer polymerized by using 100% by weight and a catalyst other than a metallocene catalyst
It is characterized by being manufactured using a gasket made of a mixture of

The above-mentioned metallocene catalyst is also called a Kaminsky catalyst or a single-site catalyst, in which a metallocene compound containing a bond of a cycloalkadienyl and a transition metal compound is used as a main catalyst and methylalumoxane (MAO) is used as a cocatalyst. Catalyst system using alumoxane or other anionic species such as.

Examples of the transition metal in the above metallocene compound include titanium, vanadium, zirconium, hafnium, niobium and tantalum. Examples of cycloalkadienyl in the above metallocene compound include cyclopentadienyl, methylcyclopentadienyl, ethylcyclopentadienyl, t-butylcyclopentadienyl, dimethylcyclopentadienyl, indenyl, 4,
5,6,7-tetrahydroindenyl and the like can be mentioned.
Specific examples of the above metallocene compound include bis (cyclopentadienyl) titanium monochloride monohydride, bis (cyclopentadienyl) titanium monobromide monohydride, bis (cyclopentadienyl) methyltitanium hydride, bis (cyclo Pentadienyl) ethyl titanium hydride, bis (indenyl) titanium monochloride monohydride,
Bis (cyclopentadienyl) titanium dichloride,
Bis (cyclopentadienyl) titanium dibromide,
Bis (cyclopentadienyl) methyltitanium monochloride, bis (cyclopentadienyl) ethyltitanium monochloride, bis (methylcyclopentadienyl)
Titanium dichloride, bis (t-butylcyclopentadienyl) titanium dichloride, bis (indenyl)
Titanium dichloride, bis (indenyl) titanium dibromide, bis (cyclopentadienyl) titanium dimethyl, ethylenebis (indenyl) dimethyltitanium, ethylenebis (indenyl) diethyltitanium, ethylenebis (indenyl) ethyltitanium monochloride, ethylenebis ( Indenyl) methyltitanium monobromide, ethylenebis (indenyl) titanium dichloride, ethylenebis (indenyl) titanium dibromide, ethylenebis (cyclopentadienyl) titanium dichloride, ethylenebis (t-butylcyclopentadienyl) titanium dichloride, ethylene Bis (4,5,6,7-tetrahydro-1-indenyl) titanium dichloride, cyclopentadienyltitanium trichloride, cycl Cyclopentadienyl titanium tribromide, cyclopentadienyl methyl titanium dichloride, compounds containing titanium as the transition metal, such as compounds represented by the cyclopentadienyl ethyl dichloride, of 5 (formula (III)),

Embedded image Bis (cyclopentadienyl) zirconium monochloride monohydride, bis (cyclopentadienyl) zirconium monobromide monohydride, bis (cyclopentadienyl) methylzirconium hydride,
Bis (cyclopentadienyl) ethyl zirconium hydride, bis (indenyl) zirconium monochloride monohydride, bis (cyclopentadienyl) zirconium dichloride, bis (cyclopentadienyl)
Zirconium dibromide, bis (cyclopentadienyl) methyl zirconium monochloride, bis (cyclopentadienyl) ethyl zirconium monochloride, bis (methylcyclopentadienyl) zirconium dichloride, bis (t-butylcyclopentadienyl) zirconium Dichloride, bis (indenyl) zirconium dichloride, bis (indenyl) zirconium dibromide,
Bis (cyclopentadienyl) zirconium dimethyl,
Ethylenebis (indenyl) dimethylzirconium, ethylenebis (indenyl) diethylzirconium, ethylenebis (indenyl) ethylzirconium monochloride, ethylenebis (indenyl) methylzirconium monobromide, ethylenebis (indenyl) zirconium dichloride, ethylenebis (indenyl) zirconium Dibromide, ethylenebis (cyclopentadienyl) zirconium dichloride, ethylenebis (t-butylcyclopentadienyl) zirconium dichloride, ethylenebis (4,5,6,7-tetrahydro-1-indenyl) zirconium dichloride, cyclopenta Dienylzirconium trichloride, cyclopentadienylzirconium tribromide, cyclopentadienylmethylzirconium dichloride Examples thereof include compounds containing zirconium as a transition metal such as cyclopentadienylethylzirconium dichloride, compounds represented by Chemical formula 6 (general formula (IV)) and Chemical formula 7 (general formula (V)). Examples include titanium or zirconium replaced with vanadium, hafnium, niobium, tantalum, and the like.

[Chemical 6]

[Chemical 7]

As a cocatalyst for the above metallocene catalyst,
Methylalumoxane (MAO), ethylalumoxane,
Alumoxanes such as propyl alumoxane, butyl alumoxane and pentyl alumoxane, or other B (C ₆
And anionic species such as F ₅ ) ₄ ⁻ .

Among the metallocene catalysts mentioned above, metallocene compounds containing a bond of cycloalkadienyl and zirconium are included among the above examples from the viewpoints of processability and physical properties of the polymerized ethylene-α-olefin copolymer. A combination of alumoxanes such as methylalumoxane (MAO) and a geometrically constrained catalyst (CGCT) exemplifying a combination of Chemical formula 5 (general formula (III)) and B (C ₆ F ₅ ) ₄ ⁻ are preferable.

As the above-mentioned metallocene catalyst, a solid catalyst in which the above metallocene compound is supported on a catalyst support such as silica, alumina or polyethylene and combined with alumoxane may be used.

The ethylene-α-olefin copolymer polymerized by using the above metallocene catalyst can be obtained by copolymerizing ethylene and an α-olefin having 3 or more carbon atoms by using a metallocene catalyst. As the α-olefin, propylene, 1-butene, 1-pentene, 1-hexene,
4-methyl-1-pentene, 1-octene, 1-decene, 1-undecene, 1-dodecene, 1-tridecene,
1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene, 1-nonadecene, 1-eicosene, 1-heneicosene, 1-dococene, 1-tricosene, 1-tetracosene, 7-methyl-1- Octene, 9-methyl-1-decene, etc. are mentioned, and these are used by 1 type (s) or 2 or more types. Among the above examples as the α-olefin, propylene, 1-butene, 1-pentene, 1-hexene, 4-methyl-1-
Pentene, 1-octene, 1-decene, 1-undecene, 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene, 1-nonadecene, 1-eicosene, etc. Having 3 to 20 carbon atoms are preferable, and those having 4 to 10 carbon atoms such as 1-butene, 1-hexene, 4-methyl-1-pentene, 1-octene and 1-decene are particularly preferable.

Examples of the polymerization process of the ethylene-α-olefin copolymer polymerized by using the metallocene catalyst described above include a high pressure polymerization method, a gas polymerization method and a solution polymerization method.

The ethylene-α-olefin copolymer polymerized by using the metallocene catalyst is an ethylene-α-olefin copolymer polymerized by using the metallocene catalyst in order to balance the physical properties such as MFR and heat resistance. A mixture of two or more polymers may be used.

The ethylene-α-olefin copolymer polymerized by using the metallocene catalyst described above is an ethylene-α-olefin copolymer polymerized by using the metallocene catalyst in order to sufficiently increase the corrosion resistance to the polymerizable monomer. 50% by weight based on the mixture of the ethylene-α olefin copolymer polymerized by using a catalyst other than the olefin copolymer and the metallocene catalyst
It is preferably not less than 80% by weight, more preferably not less than 80% by weight, even more preferably not less than 90% by weight, particularly preferably 100% by weight.

Examples of catalysts other than the metallocene catalysts mentioned above include peroxides, oxygen, chromium-based catalysts such as Phillips catalysts, Ziegler catalysts such as vanadium catalysts, and the like.
Among them, the Ziegler catalyst is particularly preferable in order to sufficiently enhance the corrosion resistance to the polymerizable monomer.

The α-olefin used in the ethylene-α-olefin copolymer polymerized by using a catalyst other than the metallocene catalyst described above is propylene, 1-butene, 1
Examples include α-olefins having 3 to 18 carbon atoms such as -pentene, 1-hexene, 4-methyl-1-pentene, 1-octene and 1-decene, and these are used alone or in combination of two or more. Among the above examples, the α-olefin preferably has 3 to 10 carbon atoms.

The ethylene-α-olefin copolymer polymerized by using a catalyst other than the metallocene catalyst described above was polymerized by using a metallocene catalyst in order to sufficiently enhance the corrosion resistance to the polymerizable monomer. It is preferably less than 50% by weight, and less than 20% by weight, based on the mixture of the ethylene-α-olefin copolymer and the ethylene-α-olefin copolymer polymerized using a catalyst other than the metallocene catalyst. More preferably, it is even more preferably less than 10% by weight, and particularly preferably 0% by weight.

The ethylene-α olefin copolymer polymerized using the metallocene catalyst described above preferably has a density of 0.85 to 0.90 g / cm ³ . When the density exceeds 0.90 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 likely to occur on the lens surface. Also, if the density is less than 0.85 g / cm ^3, it is too soft, and it becomes difficult to stably maintain the predetermined lens shape during the casting polymerization of the polymerizable monomer, and the heat resistance is likely to decrease, and the casting Easily melts during polymerization. The density is 0.87 to 0.89 g / cm in order to have a sufficiently high flexibility and to stably maintain a predetermined lens shape during casting polymerization of the polymerizable monomer and sufficiently maintain heat resistance. Those of ³ are particularly preferable.

In the above-mentioned method for producing a plastic lens, ethylene-α polymerized using a metallocene catalyst is used.
A mixture of an olefin copolymer and an ethylene-α-olefin copolymer polymerized by using a catalyst other than a metallocene catalyst can be processed into a gasket shape by injection molding, compression molding, extrusion molding or the like, From the point of view, it is preferable to process into a gasket shape by injection molding.

A mixture of the ethylene-α-olefin copolymer polymerized using the metallocene catalyst and the ethylene-α-olefin copolymer polymerized using a catalyst other than the metallocene catalyst is MFR (ASTM, D1238, E) is 1-100
It is preferably g / 10 min. MFR is 1g / 10min
If it is less than the above range, it becomes difficult to perform injection molding to form a gasket shape. If it exceeds 100 g / 10 min, the heat resistance tends to decrease. MFR is 3g / 10mi to sufficiently improve the processability when injection molding into a gasket shape.
It is more preferably n or more, and particularly preferably 8 g / 10 min or more. Further, in order to maintain the heat resistance sufficiently high, it is particularly preferable that the MFR is 70 g / 10 min or less.

A mixture of the ethylene-α-olefin copolymer polymerized using the metallocene catalyst and the ethylene-α-olefin copolymer polymerized using a catalyst other than the metallocene catalyst has a JIS A hardness of 50 or more. Those of 95 or less are preferable. If the JISA hardness is less than 50,
It becomes difficult to stably maintain a predetermined lens shape during cast polymerization of the polymerizable monomer. JIS A for the same reason
A hardness of 70 or more is particularly preferable. Also, JIS
If the A hardness exceeds 95, the sealability tends to be poor, and the gasket cannot follow the polymerization shrinkage of the lens resin during the casting polymerization to cause a sink mark on the lens surface. For the same reason, JIS A hardness of 90 or less is particularly preferable.

In the above ethylene-α-olefin copolymer, the proportion of α-olefin is preferably 1 to 70% by weight, more preferably 5 to 40% by weight, and further preferably 10 to 30% by weight. Is particularly preferable.
If the proportion of α-olefin is too large, the copolymer tends to be too soft, and if it is too small, the copolymer tends to be too hard.

In the above-mentioned method for producing a plastic lens, for example, a polymerizable monomer mixture containing a molecular weight modifier and a polymerization initiator is poured into a mold composed of two pieces of glass and a gasket, and if necessary, a clip with a spring is used. After fixing with, etc., it is cured and molded by heating.

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 method for producing a plastic lens described above, 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-butylperoxyisopropylcarbonate, 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 and 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, the molecular weight regulator used during polymerization includes general chain transfer agents, mercaptans, dialkyldisulfides,
Chloroform, carbon tetrachloride, etc. can be used,
Considering transparency, color, heat resistance and the like as a plastic lens, a 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, oxygen in the polymerizable monomer is 1.0 mg by nitrogen bubbling from the viewpoints of preventing coloration and shortening the polymerization induction period.
It is preferable to inject the polymerizable monomer into a casting mold after the amount is reduced to / l or less and to carry out the casting polymerization. From the viewpoint of preventing coloration, 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 into a prepolymer, and then a polymerization initiator is added. In addition, a polymerizable monomer can be injected into a casting mold to perform cast 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.

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 having 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 1 Tanemata is used in two or more.

Among the above monofunctional monomers, methoxynonaethylene glycol acrylate, from the viewpoint of adhesiveness and dyeability to the organic silane-based hard coat film,
Methoxy trideca ethylene glycol acrylate, methoxy tetradeca ethylene glycol acrylate, methoxy trideca ethylene glycol acrylate and other methoxy polyethylene glycol acrylate, ethoxynona ethylene glycol acrylate, ethoxy trideca ethylene glycol acrylate, ethoxy tetradeca ethylene glycol acrylate, ethoxy tricosa Ethoxy polyethylene glycol acrylate such as ethylene glycol acrylate, methoxy nonaethylene glycol methacrylate, methoxy trideca ethylene glycol methacrylate, methoxy tetradeca ethylene glycol methacrylate, methoxy trideca ethylene glycol methacrylate, etc. Over DOO, ethoxy nonaethylene glycol methacrylate, ethoxytriethylene decaethylene glycol dimethacrylate, ethoxylated tetradecanol ethylene glycol dimethacrylate, ethoxylated polyethylene glycol methacrylate such as ethoxy Trichoderma Sa ethylene glycol dimethacrylate is preferred.

Among the above-mentioned monomers having an alkylene oxide group 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. These are used in one kind or in two or more kinds. To be done.

The alkylene oxide group-containing monomer represented by the general formula (I) described above includes nonamethylene glycol diacrylate and tridecamethylene glycol among the above examples 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 diacrylate, 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) acrylates having 2 to 3 carbon atoms in the alkylene oxide group such as polyethylene glycol polypropylene glycol dimethacrylate such as tetradecaethylene glycol tripropylene glycol dimethacrylate are more 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 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, there is a problem that 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. 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.

Among the polyfunctional (meth) acrylates represented by the general formula (II), among the above 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 monofunctional monomers 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, tricyclomethacrylate [5.2.1.0 ^2,6 ] deca-4-methyl, cyclodecyl methacrylate, methacrylic acid esters such as glycerin monomethacrylate, styrene , Α-methylstyrene, α-ethylstyrene, α-fluorostyrene, α-
Aromatic vinyl compounds such as chlorostyrene, α-bromostyrene, fluorostyrene, chlorostyrene, bromostyrene, methylstyrene and methoxystyrene, N-methylmaleimide, N-ethylmaleimide, N-propylmaleimide, N-butylmaleimide, N -Cyclohexylmaleimide, N-phenylmaleimide, N-methylphenylmaleimide, N-chlorophenylmaleimide, N
-N-substituted maleimide acrylamides such as methoxyphenyl maleimide, N-carboxyphenyl maleimide, methacrylamide, N dimethyl acrylamide, N
-(Meth) acrylamides such as diethyl acrylamide, N-dimethyl methacrylamide, N-diethyl methacrylamide, calcium acrylate, barium acrylate, lead acrylate, tin acrylate, zinc acrylate, calcium methacrylate, barium methacrylate ,
(Meth) acrylic acid metal salts such as lead methacrylate, tin methacrylate, zinc methacrylate, unsaturated carboxylic acids such as acrylic acid and methacrylic acid, glycidyl acrylate,
Epoxy group-containing vinyl compounds such as glycidyl methacrylate, hydroxyethyl acrylate, hydroxy group-containing vinyl compounds such as hydroxyethyl methacrylate, γ-
Examples thereof include alkoxysilyl group-containing vinyl compounds such as (methacryloxypropyl) trimethoxysilane, vinyl cyanide compounds such as acrylonitrile and methacrylonitrile, and these may be used alone or in combination of two or more.

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 , Hexamethylolmelamine hexaacrylate, acrylic acid ester such as 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 bi Allyl carbonate, tetraethylene glycol bisallyl carbonate, pentaethylene glycol bisallyl carbonate, polypropylene glycol bisallyl carbonate, trimethylene glycol bisallyl carbonate, 3-hydroxypropoxy propanol bisallyl carbonate, glycerine bisallyl carbonate, triglycerine bisallyl 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-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, Examples thereof include diallyl 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, methacryl 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.

When the amount of styrene used is small, it becomes 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, keeping the refractive index at 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 or an alkoxysilyl group-containing vinyl compound, which is one of the other copolymerizable vinyl-based monomers, is 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.

In the use of the above-mentioned plastic lens, from the viewpoints of deterioration prevention, thermal stability, processability, etc., phosphite-based, phenol-based, thioether-based antioxidants, aliphatic alcohols, fatty acid esters,
Phthalates, triglycerides, fluorine-based surfactants, release agents such as higher fatty acid metal salts, other lubricants,
You may add and use a plasticizer, an antistatic agent, an 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 described above, M
An inorganic compound such as gF ₂ or 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 on the lens surface, a vinyl monomer, a melamine resin,
By hard coating epoxy resin, fluorine resin, silicone resin, etc., moisture resistance, optical characteristics,
It is possible to improve chemical resistance, abrasion resistance, antifog and the like.

On the surface of the plastic lens described above,
An organic silane-based hard coat film and a cured film of an organic silane resin can be directly laminated.

The above-mentioned organic silane resin is, for example,

Embedded image (Wherein R ⁸ is an organic group containing an epoxy group having 2 to ⁸ carbon atoms, R ⁹ is an alkyl group, an alkenyl group, a halogenated alkyl group or an allyl group having 1 to 6 carbon atoms, R ¹⁰ is a hydrogen atom, Is 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), or a partial hydrolyzate thereof. 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. As a commercial product, KP64C (Shin-Etsu Chemical
(Trade name) etc.

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. The added product is directly applied to the surface of the plastic lens described above, and 50 to 1
A hard coat layer can be formed by heating and curing at 40 ° C. 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 a surface treatment such as plasma treatment. The plastic lens described above does not require these pretreatments.

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

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

The above 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. Examples include CI Disperse Red 13, 56, 112, CI Disperse Yellow 3, 7, 31, 42, 54, 198, CI Disperse Blue 1, 3, 5, 54, 56, 197.

At the time of the above-mentioned dyeing, by adding a dyeing aid such as a pH adjusting agent, a wetting agent, a surfactant, a dispersion accelerator, an antifoaming agent, etc., the dyeing strength and the dyeing uniformity can be improved. be able to.

At the time of 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.

[0078]

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.

Examples 1 to 3 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 [5.2.1.0 ^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.

[0080]

[Table 1]

Comparative Examples 1 to 3 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.

[0082]

[Table 2]

In Examples 1 to 3 and Comparative Examples 1 to 3,
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.

[0084]

[Table 3]

[0085]

[Table 4]

Examples 4 to 6 SM1250 (Ethylene-α olefin copolymer polymerized using metallocene catalyst, Dow Chemical Co., Ltd.)
A glass plate having two lens-like irregularities was fixed with a clip with a spring via a gasket consisting of, and a 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, 20 parts by weight of 2,2-dimethyl-1,3-propanediol dimethacrylate, The polymerization initiator shown in Table 5 was added to a polymerizable monomer consisting of 15 parts by weight of tetradecaethylene glycol dimethacrylate and 1.0 part by weight of a dimer of α-methylstyrene, and the mixture was sufficiently stirred, and It was poured into a 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.

[0087]

[Table 5]

In Examples 4 to 6, the heat resistance of the gasket at the time of casting polymerization, the cloudiness of the obtained lens due to the erosion of the gasket, the casting moldability, etc. were examined and shown in Table 6.

[0089]

[Table 6]

Examples 7 to 17 SM1250 (Ethylene-α olefin copolymer polymerized by using metallocene catalyst, manufactured by Dow Chemical Co., Ltd.)
A glass plate having two lens-like irregularities was fixed with a clip with a spring via a gasket consisting of, and a casting mold was assembled. Next, the polymerizable monomer having the composition shown in Table 7 was added to the polymerizable monomer as a polymerization initiator with diisopropyl peroxydicarbonate (10-hour half-life temperature: 4
0.5 ° C.) 1.0 part by weight, t-butylperoxy (2-
Ethyl hexanoate) (10-hour half-life temperature: 72.
(5 ° C.) 0.5 part by weight and sufficiently stirred, then poured into the above casting mold and kept at 25 ° C. for 6 hours.
The temperature was raised to 80 ° C. over 7 hours. The cured lens is removed from the mold, heat-treated at 120 ° C for 2 hours, then cooled to room temperature, and an organic silane-based hard coating agent (trade name "KP"
64C ″ Shin-Etsu Chemical Co., Ltd. was applied by dip coating, and heat-cured at room temperature for 30 minutes, 90 ° C. for 30 minutes, and 120 ° C. for 1 hour.

[0091]

[Table 7]

The lenses obtained in Examples 7 to 17 were examined for refractive index, Abbe number, specific gravity, heat resistance, puncture tensile strength, hue, hard coat adhesion, dyeability, cloudiness due to gasket erosion and the like, and Table 8 It was shown to.

[0093]

[Table 8]

Examples 18 to 33 SM1250 (Ethylene-α olefin copolymer polymerized by using metallocene catalyst, manufactured by Dow Chemical Co.)
A glass plate having two lens-like irregularities was fixed with a clip with a spring via a gasket consisting of, and a 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 by diisopropyl peroxydicarbonate (10-hour half-life temperature: 4
0.5 ° C.) 1.0 part by weight, t-butylperoxy (2-
Ethyl hexanoate) (10-hour half-life temperature: 72.
(5 ° C.) 0.5 part by weight and sufficiently stirred, then poured into the above casting mold and kept at 25 ° C. for 6 hours.
The temperature was raised to 80 ° C. over 7 hours. The cured lens is removed from the mold, heat-treated at 120 ° C for 2 hours, then cooled to room temperature, and an organic silane-based hard coating agent (trade name "KP"
64C ″ Shin-Etsu Chemical Co., Ltd. was applied by dip coating, and heat-cured at room temperature for 30 minutes, 90 ° C. for 30 minutes, and 120 ° C. for 1 hour.

[0095]

[Table 9]

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

[0097]

[Table 10]

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 III manufactured by Cabin Industry) to evaluate the degree of cloudiness due to erosion. (Evaluation) ○: Transparent, ×: Cloudy ・ Castability of lens casting: Casting polymerization of the lens obtained by performing casting polymerization using each gasket was evaluated. 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 Ts (softening temperature) and penetration amount (thermal deformation amount). -Pulling tensile strength: A 2.0 mm diameter hole was made at each end of a 2 mm thick lens, 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: 1 mm with a knife on the hard coat film
Eleven vertical and horizontal grids were placed at intervals, cellophane tape (manufactured by Nichiban) was adhered, and the cellophane tape was rapidly peeled off to check the number of squares which were not peeled off. Evaluation: ◯ is 80 to 100/100. X is 0 to 20
/ 100. Dyeability: 5 g of the dye, 2 ml of the dispersion aid, and 10 g of benzyl methacrylate were dissolved in 1 liter 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, SM1250 is an affinity SM1250 (ethylene-α olefin copolymer polymerized using a metallocene catalyst, manufactured by Dow Chemical Co., Ltd.
SM1300 is an affinity SM1300 (ethylene-α olefin copolymer polymerized using a metallocene catalyst, manufactured by Dow Chemical Co., Ltd.), SM1350 is an affinity SM1350 (ethylene-α olefin polymerized using a metallocene catalyst). Copolymer, manufactured by Dow Chemical Co., Ltd., EUL730 and EUL430 are ethylene-α olefin copolymers (manufactured by Sumitomo Chemical Co., Ltd.) polymerized using a Ziegler catalyst, DPDJ is DPDJ9169.
(Ethylene-ethyl acrylate elastomer, manufactured by Nippon Unicar Co., Ltd.) is shown. 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-
Ethyl hexanoate) (10-hour half-life temperature: 72.
5 ° C) ST is styrene, MMA is methyl methacrylate, TCD
MA is tricyclomethacrylate [5.2.1.0 ^2,6 ].
Deca-8-yl, NPDM is 2,2-dimethyl-1,3
-Propanediol dimethacrylate, EGDM is ethylene glycol dimethacrylate, 4EGDM is tetraethylene glycol dimethacrylate, DDDM is 1.
10-decanediol dimethacrylate, 14EGDM
Is tetradecaethylene glycol dimethacrylate, N
PDA is 2,2-dimethyl-1,3-propanediol diacrylate, 9EGDM is nonaethylene glycol dimethacrylate, 9EGMM is nonaethylene glycol monomethacrylate, HEMA is 2-hydroxyethyl methacrylate, and α-MSD is α-methylstyrene. The dimer, NOM, is n-octyl mercaptan. α
-The amount of MSD and NOM used is shown by weight% based on all monomers.

[0100]

The gasket for producing a plastic lens according to the first aspect is excellent in erosion resistance against polymerizable monomers including aromatic monomers. The gasket for producing a plastic lens according to a second aspect has the same effect as the gasket for producing a plastic lens according to the first aspect, and further has excellent flexibility, so that it easily follows the polymerization shrinkage of the lens resin during the casting polymerization. The plastic lens manufacturing gasket according to claim 3 has the same effect as the plastic lens manufacturing gasket according to claim 1, and is further excellent in productivity. The plastic lens obtained by the method according to claim 4 has no cloudiness or coloring and is excellent in transparency. The plastic lens obtained by the method of claim 5 has the effect of the plastic lens of claim 4, and is also excellent in castability. The plastic lens obtained by the method according to the sixth aspect exhibits the effect of the plastic lens according to the fourth aspect and is further excellent in productivity. The plastic lens obtained by the method according to claim 7 exhibits the effect of the plastic lens according to claim 4, and is further excellent in high refractivity. A plastic lens obtained by the method according to claim 8 has the effect of the plastic lens according to claim 4, and
It is possible to directly coat a cured film of organosilane resin (organosilane-based hard coat film) because of its excellent hue, strength at the time of punching, dyeability, low specific gravity, and excellent adhesion to organosilane resin. it can. The plastic lens according to claim 9 is excellent in transparency without clouding or coloring. The plastic lens according to claim 10 has the effect of the plastic lens according to claim 9, and is further excellent in castability. The plastic lens according to claim 11 has the effect of the plastic lens according to claim 9, and is further excellent in productivity. A plastic lens according to a twelfth aspect has the effect of the plastic lens according to the ninth aspect and is further excellent in high refractivity. Claim 13
The plastic lens according to claim 9 has the effects of the plastic lens according to claim 9, and further has excellent hue, strength at the time of punching, excellent dyeability, low specific gravity, and excellent adhesiveness to an organic silane resin. A cured film of silane resin (organic silane-based hard coat film) can be coated.

Claims (13)

[Claims] 1. An ethylene-α olefin copolymer polymerized with a metallocene catalyst in an amount of 10 to 100% by weight and an ethylene-α polymerized with a catalyst other than the metallocene catalyst.
A gasket for producing a plastic lens, which comprises a mixture of 90 to 0% by weight of an olefin copolymer. 2. The density of the ethylene-α-olefin copolymer polymerized with the metallocene catalyst is 0.85 to 0.9.
The gasket for producing a plastic lens according to claim 1, wherein the gasket is 0 g / cm ³ . 3. An MFR (ASTM, D1238, E) of a mixture of an ethylene-α-olefin copolymer polymerized with a metallocene catalyst and an ethylene-α-olefin copolymer polymerized with a catalyst other than the metallocene catalyst. ) Is 1 to 100 g / 10
The gasket for producing a plastic lens according to claim 1, wherein the gasket is min. 4. An ethylene polymerized using a metallocene catalyst when a polymerizable monomer is injected into a plastic lens casting mold sealed with a gasket and cast polymerization is carried out to produce a plastic lens. A plastic lens using a gasket comprising a mixture of 10 to 100% by weight of an α-olefin copolymer and 90 to 0% by weight of an ethylene-α-olefin copolymer polymerized by using a catalyst other than a metallocene catalyst. Manufacturing method. 5. The ethylene-α olefin copolymer polymerized with a metallocene catalyst has a density of 0.85 to 0.9.
The method for producing a plastic lens according to claim 4, wherein the plastic lens is 0 g / cm ³ . 6. An MFR (ASTM, D1238, E) of a mixture of an ethylene-α-olefin copolymer polymerized with a metallocene catalyst and an ethylene-α-olefin copolymer polymerized with a catalyst other than the metallocene catalyst. ) Is 1 to 100 g / 10
5. The method for manufacturing a plastic lens according to claim 4, wherein the value is min. 7. The method for producing a plastic lens according to claim 4, wherein the polymerizable monomer is a monomer mixture containing at least one aromatic monomer. 8. The polymerizable monomer has the general formula (I): (However, R ¹ is an acryloyl group or a methacryloyl group, R ² is an alkylene group having 1 to 5 carbon atoms, and R ³ is hydrogen, an acryloyl group, a methacryloyl group or a C 1 to 40 other than these group. 1 to 50 parts by weight of a monomer containing an alkylene oxide group represented by a monovalent hydrocarbon group and m is an integer of 9 to 50, and a compound represented by the general formula (II): (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) 1 to 50 parts by weight of a polyfunctional (meth) acrylate, and 15 to 15 parts of styrene. The method for producing a plastic lens according to claim 7, which is a monomer mixture in which 60 parts by weight and 0 to 60 parts by weight of another copolymerizable vinyl monomer are blended so as to be 100 parts by weight as a whole. . 9. An ethylene polymerized using a metallocene catalyst when a plastic monomer is produced by injecting a polymerizable monomer into a plastic lens casting mold which is sealed with a gasket and cast-polymerized. It is characterized by using a gasket made of a mixture of 10 to 100% by weight of an α-olefin copolymer and 90 to 0% by weight of an ethylene-α-olefin copolymer polymerized by using a catalyst other than a metallocene catalyst. Plastic lens. 10. The density of the ethylene-α-olefin copolymer polymerized using a metallocene catalyst is 0.85 to 0.
The plastic lens according to claim 9, which has a weight of 90 g / cm ³ . 11. An MFR (ASTM, D1238, E) of a mixture of an ethylene-α olefin copolymer polymerized with a metallocene catalyst and an ethylene-α olefin copolymer polymerized with a catalyst other than the metallocene catalyst. ) Is 1 to 100 g / 1
The plastic lens according to claim 9, wherein the plastic lens has a length of 0 min. 12. The plastic lens according to claim 9, wherein the polymerizable monomer is a monomer mixture containing at least one aromatic monomer. 13. The polymerizable monomer is represented by the general formula (I): (However, R ¹ is an acryloyl group or a methacryloyl group, R ² is an alkylene group having 1 to 5 carbon atoms, R ³ is hydrogen, an acryloyl group, a methacryloyl group or a C 1 to 40 other than these group. 1 to 50 parts by weight of a monomer containing an alkylene oxide group represented by a monovalent hydrocarbon group and m is an integer of 9 to 50, and a compound represented by the general formula (II): (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) 1 to 50 parts by weight of a polyfunctional (meth) acrylate and 15 to 15 parts of styrene. 13. The plastic lens according to claim 12, which is a monomer mixture prepared by mixing 60 parts by weight and 0 to 60 parts by weight of another copolymerizable vinyl monomer so that the total amount is 100 parts by weight.