JPH0451801B2 - - Google Patents

Description

[Detailed description of the invention]

[Industrial Application Field] The present invention relates to a high refractive index eyeglass plastic lens with excellent transparency and color tone. [Prior Art] Plastic lenses have become popular as eyeglass lenses instead of glass lenses. Plastic lenses have advantages over glass lenses, such as being lightweight, easy to dye, impact resistance, and easy to process, and are already available in polymethyl methacrylate resin, polycarbonate resin, polydiethylene glycol bisallyl carbonate resin, polystyrene resin, etc. is being used. Among these, polydiethylene glycol bisallyl carbonate resin, which is a thermosetting resin, is especially suitable for vision correction lenses because it is lightweight, has excellent safety, especially impact resistance, and has good machinability in cutting and polishing. It is widely used because it has many advantages. However, polydiethylene glycol biaryl carbonate resin has a refractive index of 1.50, and when it is made into a concave lens, it has the disadvantage that the peripheral thickness of the lens becomes larger than that of a glass lens. This is particularly noticeable when the power of the lens increases. In order to solve these problems, various high refractive index plastic lens resins have been proposed. Generally, in order to obtain a resin having a high refractive index, it is effective for the monomer to contain an aromatic ring, a halogen element other than fluorine, and a metal salt. By the way, since there is a problem that the original lightweight characteristic of plastic lenses is lost, it is generally done to use an aromatic vinyl monomer or a nuclear halogen-substituted aromatic vinyl monomer in combination with. It is. For example, Japanese Patent Publication No. 58-17527 describes that a copolymer of bisphenol A dimethacrylate and styrene gives a refractive index of 1.588; A copolymer of diacrylate and bisphenoloxyethyl acrylate having an A group is
It is described to give a refractive index of 1.600 and is also
JP-A-59-191708 describes that a copolymer mainly composed of diacrylate having a bisphenol A group and diallylisophthalate gives a refractive index of 1.55 to 1.57. As an example of the use of styrene and diacrylate in combination, Japanese Patent Publication No. 58-14449 describes that a copolymer of diacrylate and styrene having a tetrabromo bisphenol A group gives a refractive index of 1.590. Publication No. 8709 describes that a copolymer of tetrabromoterephthalic acid diallyl ester and phenyl methacrylate gives a refractive index of 1.591.
Publication No. 12501 discloses a copolymer of tetrachlorophthalic acid diallyl ester and monochlorostyrene.
It is described to give a refractive index of 1.600 to 1.609. By the way, it is a well-known phenomenon that compounds with conjugated double bonds, represented by aromatic rings, are sensitive to heat or light.In fact, when polymerizing compounds containing aromatic rings, polymerization initiation There is a problem in that coloring tends to progress depending on the type and amount of peroxide used as an agent, or heating conditions. Furthermore, if the obtained lens molded body is left under ultraviolet rays such as when exposed outdoors, there is a problem in that the coloring increases. On the other hand, regarding organic compounds containing halogens,
It is easily released by heat or light such as ultraviolet rays, and there is a problem with coloring. Such a decrease in color tone due to heat or light, that is, coloration, tends to be further accelerated when an aromatic ring and an organic halogen compound coexist. This phenomenon and analysis can be found in J.Appl.
It is detailed in POlm.Sci. , 20, 463 (1976), etc. In reality, excessive antioxidants,
This has been countered by adding ultraviolet absorbers, etc., but a decline in polymerization formability is unavoidable, and the transparency and color tone of the molded products are not necessarily sufficient. [Problems to be Solved by the Invention] In order to produce a plastic lens with a high refractive index, as mentioned above, a polyfunctional organic compound containing an aromatic ring or a nuclear halogen other than fluorine is used. Although it is effective to use polyfunctional organic compounds containing elements and aromatic rings, they all have the problem of being sensitive to heat, light, etc. and easily colored during polymerization or when exposed outdoors. In addition, JP-A-52-104940 discloses a technique for coloring a lens formed by polymerizing a composition partially containing an unsaturated compound by adding a dye to the composition. There is. However, even in this technique, no consideration was given to making the lens colorless. An object of the present invention is to provide a high refractive index plastic lens that solves these problems and has excellent not only refractive index, transparency, and color tone, but also mechanical properties (rigidity, impact resistance), and heat resistance. It is in. Another object of the present invention is to provide a high refractive index plastic lens that is resistant to coloration even when left under ultraviolet rays such as heating or outdoor exposure. [Means for Solving the Problems] As a result of extensive research by the present inventors on high refractive index plastic lenses that solve the above problems,
This led to the present invention. That is, the present invention consists of the following configuration. A high refractive index plastic lens made of a polymer crosslinked with a radically polymerizable polyfunctional organic vinyl monomer containing an aromatic ring and having a refractive index nd of 1.50 or more, a dye selected from among blue dyes and a red dye. A high refractive index plastic lens characterized by being substantially colorless because it contains a dye that is a complementary color to the color tone of the lens, which is a mixture of a dye selected from violet dyes and violet dyes. The high refractive index plastic lens with excellent color tone of the present invention is produced by polymerizing a radically polymerizable polyfunctional organic vinyl monomer containing an aromatic ring and having the above-mentioned refractive index nd of 1.50 or more. When the polyfunctional organic vinyl monomer containing such an aromatic ring and capable of radical polymerization contains a halogen element other than fluorine, a more favorable effect is exhibited. When a disperse dye is used as the dye used to improve the color tone of the present invention, it improves the color tone not only when the lens is molded, but also when the lens is left under heating or under ultraviolet light such as when exposed outdoors. It is characterized by its good effects. In the present invention, the following can be mentioned as a radically polymerizable polyfunctional organic vinyl monomer containing an aromatic ring having a refractive index nd of 1.50 or more. Terephthalic acid bisallyl ester, isophthalic acid bisallyl ester, trimethic acid triallyl ester, terephthalic acid bis(aryloxycarbonylmethyl) ester, 5,5'-dimethylbuphenyl-3,3'-dicarboxylic acid allyl ester,
Polyvalent allyl esters such as 1,9-dimethoxynaphthalene-3,7-dicarboxylic acid allyl ester, 1,1'-dimethyldiphenylmethane-3,3'-dicarboxylic acid allyl ester, 1,3-benzene bisallyl carbonate , 1,4-naphthalene bisallyl carbonate, 1,5-naphthalene bisallyl carbonate, 1,6-naphthalene bisallyl carbonate, 1,7-naphthalene bisallyl carbonate, 2,6-naphthalene bisallyl carbonate, 2,7- Naphthalene bisallyl carbonate, 4,4'-diphenylpropane bisallyl carbonate, 4,4'-diphenylsulfone bisallyl carbonate, 1,3-bis(hydroxyethoxy)benzene bisallyl carbonate, 1,4-bis(hydroxy) ethoxy)benzenebisallyl carbonate, 1,5-bis(hydroxyethoxy)naphthalenebisallyl carbonate, 1,6-bis(hydroxyethoxy)naphthalenebisallyl carbonate, 1,7-bis(hydroxyethoxy)naphthalenebisallyl carbonate, 2 , 6-bis(hydroxyethoxy)naphthalene bisallyl carbonate, 2,7
- Polyvalent allyls such as bis(hydroxyethoxy)naphthalene bisallyl carbonate, 4,4'-bis(hydroxyethoxy2)diphenylpropane bisallyl carbonate, and 4,4'-bis(hydroxyethoxy)diphenylsulfone bisalcarbonate. carbonate, 1,4-diacryloxybenzene, 1,4-dimethacryloxybenzene,
1,4-diacryloxyethoxybenzene, 1,
4-dimethacryloxyethoxybenzene, 1,5
- diacryloxinaphthalene, 1,5-dimethacryloxinaphthalene, 1,5-bis(β-acryloxyethoxy)naphthalene, 1,5-bis(β
-methacryloxyethoxy)naphthalene, 2,
2'-bisacryloxybiphenyl, 2,2'-bismethacryloxybiphenyl, 2,2'-bis(β-
acryloxyethoxy)biphenyl, 2,2′-bis(β-methacryloxyethoxy)biphenyl,
2,2-bis(4-acryloxyphenyl)propane, 2,2-bis(4-methacryloxyphenyl)propane, 2,2-bis(4-acryloxyethoxyphenyl)propane, 2,2- Screw (4
-methacryloxyethoxy)phenylpropane,
2,2'-bis(4-acryloxypolyethoxyphenyl)propane, 2,2-bis(4-methacryloxypolyethoxyphenyl)propane, 2,
2'-bis(4-acryloxyethoxyphenyl)
Sulfone, 2,2'-bis(methacryloxyphenyl)sulfone, 2,2'-bis(3-acryloyl-2-hydroxypropoxy)biphenyl, 2,
2'-bis(3-methacryloyl-2-hydroxypropoxy)biphenyl, 2,2'-bis(3-acryloyl-2-hydroxypropoxyphenyl)propane, 2,2'-bis(3-methacryloyl-2-hydroxy) Examples include polyvalent (meth)acrylates such as (propoxyphenyl)propane, and polyvalent vinyl compounds such as divinylbenzene and divinylnaphthalene. Further, compounds in which the aromatic ring in these compounds is substituted with a nuclear halogen can be mentioned as polyfunctional organic vinyl monomers containing the above-mentioned halogen element and capable of radical polymerization. These monomer compounds can be used not only alone, but also in a mixture of two or more. Among the above monomer compounds, particularly preferred are divinylbenzene, 2,2-bis(4-methacryloxyethoxy-3,5'-dibromophenyl)propane, 2,2-bis(4-acryloxy Ethoxy-3,5-dibromophenyl)propane, diallyl phthalate, diallyl isophthalate, 2,2-bis(4-methacryloxyethoxy-3,5-dibromophenyl)fluorone, 2,2
-bis(4-acryloxyethoxy-3,5-dibromophenyl)sulfone, tetrabromophthalic acid diallyl ester, tetrabromoterephthalic acid diallyl ester, and the like. Further, in the present invention, the polyfunctional organic vinyl monomer having a refractive index nd of 1.50 or more, containing an aromatic ring, and capable of radical polymerization is a monomer having one radical polymerizable double bond in the molecule. Even if the molecule contains a functional group such as -OH, -NCO, -COOH, _-NH2 , or epoxy group, the double bond obtained by intermolecular bonding through the functional group A monomer compound containing a plurality of bonds can be used alone or in combination with the various monomers described above. As such a monomer compound, 1-vinyl-4-
An addition reaction product obtained by reacting 2 moles of hydroxybenzene with 1 mole of hexamethylene diisocyanate, an addition reaction product obtained by reacting 2 moles of bisphenol A monoacrylate with 1 mole of xylylene diisocyanate, and 2 moles of methacrylic acid.
An addition reaction product reacted with 1 mole of 2,2-bis(4-glycidoxyphenyl)propane, an addition reaction product reacted with 1 mole of 4-hydroxyphenyl methacrylate, 1 mole of glycidyl methacrylate, and 2 moles of vinyl acetic acid. An addition reaction product reacted with 1 mole of xylylene diamine can be used. In the present invention, in addition to the aromatic ring-containing and radically polymerizable polyfunctional organic vinyl monomer, monofunctional monomers having a radically polymerizable double bond are used, depending on the degree of various properties desired for the eyeglass lens. Monomers can also be added. Such monomers include styrene, monochlorostyrene, dichlorostyrene, monobromostyrene, dibromostyrene, phenyl acrylate, phenyl methacrylate, monochlorophenylacrylate, monochlorophenyl methacrylate, dichlorophenyl acrylate, dichlorophenyl. methacrylate,
Trichlorophenyl acrylate, trichlorophenyl methacrylate, monobromophenyl acrylate, monobromophenyl methacrylate,
Dibromophenyl acrylate, dibromophenyl methacrylate, tribromophenyl acrylate, tribromophenyl methacrylate, pentabromophenyl methacrylate, pentabromophenyl methacrylate, monochlorophenoxyethyl acrylate, monochlorophenoxyethyl methacrylate, dichloro Phenoxyethyl acrylate, dichlorophenoxyethyl methacrylate, trichlorophenoxyethyl acrylate, trichlorophenoxyethyl methacrylate, monobromophenoxyethyl acrylate,
Monobromophenoxyethyl methacrylate, dibromophenoxyethyl acrylate, dibromophenoxyethimetal acrylate, tribromophenoxyethyl acrylate, tribromophenoxyethyl methacrylate, pentabromophenoxyethyl acrylate, pentabromophenoxy Ethyl methacrylate, benzyl acrylate, benzyl methacrylate, bromobenzyl acrylate, dibromobenzyl acrylate, α-
Naphthyl acrylate, α-naphthyl methacrylate, β-naphthyl acrylate, β-naphthyl methacrylate, ethyl acrylate, ethyl methacrylate, tribromopentyl acrylate, tribromopentyl methacrylate, 2,3
Examples include -dibromopropyl acrylate, phenyl acrylic carbonate, benzyl allyl carbonate, allyl benzoate, allyl naphthalenecarboxylate, and halogen-substituted products thereof. The composition ratio of the radically polymerizable polyfunctional organic vinyl monomer containing an aromatic ring, which is an essential component in the present invention, and the monofunctional monomer is determined by the optical properties and mechanical properties required for a desired eyeglass lens. It cannot be determined uniformly because it varies depending on physical characteristics, thermal characteristics, etc.
It is preferable that the amount of the polyfunctional organic vinyl monomer containing an aromatic ring and capable of radical polymerization, which is an essential component in the present invention, is 5% by weight or more, preferably 10% by weight or more. If it is less than 5% by weight, crosslinking is insufficient, resulting in poor cutting and polishing workability, heat softening resistance, and impact resistance. The dye used in the present invention is selected from commercially available synthetic dyes that have an azo group, an anthraquinone structure,
Dyes containing at least one fused polycyclic quinone or heterocycle in one molecule and which are used industrially as disperse dyes can be used. Examples of these disperse dyes include the Dianix Blue series (B-SE, KR-
FS, RC-E, RN-E, AC-E, EB-E, KB
-FS, BG-FS, HB-FS, KG-SE, GR-E,
(Mitsubishi Chemical Industries product)), Miketon Polyester Blue
Series (GFL, SG, 3G, BLN, BCL,
TGSF, GRN, (Mitsui Toatsu Chemicals product)), Kayalon
Polyester Blue series (GRF, 3GF, GGF,
BBF, TSF, RGF (Nippon Kayaku Co., Ltd. product)),
Sumikaron Blue series (GG, BR, R, BG,
(Sumitomo Chemical Co., Ltd. product)), red dyes such as
Dianix Red series (R-E, 3G-FS, G-
SE, BG-FS, FL-FS, U-SE, AC-E,
BN-SE, B-FS, KB-SE, (Mitsubishi Chemical Industries product)), Miketon Polyester Red series (FB,
FL, 2BSF, FN, (Mitsui Toatsu Chemicals product)),
Kayalon Polyester Red Series (Rubine−
FSF, BRSF, BSF, LSF, 2BSF (Nippon Kayaku Co., Ltd.)), Sumikaron Red series (3G, FB,
3BR, BGS, B, G, 2gs, (Sumitomo Chemical products)) and other purple dyes include Dianix Violet series (5R-SE, 3R-FS, 2R-E (Mitsubishi Chemical Industries products)), Miketon Polyester Violet Series (BN, FR (Mitsui Toatsu Chemicals product)), Kayalon
Polyester Violet series (BNF, RNF (Nippon Kayaku Co., Ltd.)), Sumikaron Violet series (RR,
Examples include R and RS (Sumitomo Chemical products). To carry out the present invention, a disperse dye having a color tone complementary to that of the monomer (singlely or as a mixture) prepared for lens molding is added and thoroughly mixed. The amount of the disperse dye added is determined by the fact that the coloring of the lens-forming monomer disappears by adding the dye. Changes in color tone can be easily observed by visual observation, but it is best to measure the x and y values of the CIE (Commission Internationale de l'Eclairage) color system using a color computer (model SM-3, Suga Test Instruments Co., Ltd.). This makes it possible to detect slight changes in color tone and easily control the amount of dye added. The amount of dye added is generally 0.001~
1000 ppm, preferably in the range of 0.01 to 100 ppm. If it is less than 0.01 ppm, the effect of improving the color tone is poor, and if it exceeds 100 ppm, the color of the dye becomes dominant, the phenomenon of transmitted light becomes noticeable, and the function as an eyeglass lens deteriorates. Lens molding is mainly performed by cast polymerization. Depending on the selection of polymerization conditions,
Even if a colorless lens monomer is used, the molded lens may be colored. In such a case, the color tone can be improved by increasing the amount of disperse dye added to the molding monomer depending on the degree of coloration of the lens. A lens with improved color tone described here means that the absorption is uniform and small for each wavelength in the visible region, and there is no strong absorption at a specific wavelength. The presence of disperse dye in the lens
It can be analyzed using spectroscopic methods such as UV spectra and fluorescence spectra. For polymerization, known radical polymerization methods, photopolymerization methods, etc. can be employed. That is, after using the above monomers alone or after mixing the various monomers above, a polymerization initiator such as diisopropyl peroxydicarbonate,
Dimyristyl peroxydicarbonate, tertiary butyl peroxy pivalate, lauroyl peroxide, tertiary butyl peroxyisobutyrate, tertiary butyl peroxyisopropyl carbonate, ditertiary butyl peroxide, benzoyl peroxide,
Azodiisobutyronitrile, Azobister Shiary Octane, etc., per 100 parts by weight of monomer, 0.01
~10 parts by weight are mixed. The resulting mixture is poured into a mold prepared in advance and heated gradually to complete polymerization. At this time, it is also possible to terminate the polymerization midway, take out the prepolymer from the mold, and complete the polymerization again with the prepolymer and the polymerization initiator. Polymerization temperature and polymerization time vary depending on the type of monomers used, the composition ratio, and the selection of polymerization initiator, so they cannot be uniformly limited, but they are generally 40 to 150℃ and 1 to 100℃.
It is preferable to complete the polymerization over time. Further, the resin of the present invention can also be produced using a photopolymerization method. That is, after using the above monomer alone or mixing the various monomers mentioned above, a photosensitizer such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzophenone, 2-hydroxy-2-methyl-propiophenone, 0.01 to 10% of benzyl dimethyl ketal, benzoin isopropyl ether, acetophenone, dimethoxyacetophenone, 1-chloroanthraquinone, 1,4-naphthoquinone, etc. per 100 parts by weight of monomer.
The parts by weight are mixed and polymerized by irradiation with an ultraviolet lamp, mercury lamp, etc. In this case, it is also possible to partially use a polymerization initiator. In manufacturing the high refractive index plastic lens with excellent color tone of the present invention, in addition to the above-mentioned essential ingredients, additives such as antistatic agents, anticoloring agents, surface smoothing agents, ultraviolet absorbers, and antioxidants are added. It is possible to improve practicality by blending.
For example, antistatic agents include nonionic surfactants and quaternary ammonium salts; anticoloring agents include triphenylphosphine, triphenylantimony, and triphenyl arsenic; and surface smoothing agents include silicone compounds, Examples of ultraviolet absorbers such as fluorine surfactants and organic surfactants include 2-(hydroxy-5-methylphenyl)benzotriazole, 2-(hydroxy-5-tert-butylphenyl)benzotriazole,
Antioxidants such as 2-(3',5'-ditertiarybutyl-2-hydroxyphenyl)-benzotriazole, 2-hydroxy-4-n-octoxybenzophenone, hindered phenols, hindered amines, etc. etc. can be added. The plastic lens of the present invention can be subjected to surface modification such as antireflection, high hardness, abrasion resistance, improved chemical resistance, and antifogging properties, and can be subjected to known physical or chemical methods. . In particular, two layers of coatings with different refractive indexes are formed on the surface to provide anti-reflection treatment, polysiloxane, silica sol, etc. are applied to form a highly hard coating on the surface, and this is dyed to make it durable. It is preferable to form a metal film on the surface by means such as vapor deposition to give a mirror effect, and to form a hygroscopic film on the surface to prevent fogging. [Example] In the following Examples and Comparative Examples, various physical properties were measured by the following test methods. (1) Refractive index and Atsbe number Measured at 20°C using a Pulfritsch refractometer. The wavelength is the value at the D line of 58929 Å. (2) Total light transmittance The total light transmittance of the lens molded product was determined by measuring the Y value of the CIE (Commission Internationale de l'Eclairage) color system using a color computer (model SM-3, Suga Test Instruments Co., Ltd.). The transmittance was determined. (3) Color tone The color tone of the lens molded product was measured by CIE using a color computer (model SM-3, Suga Test Instruments Co., Ltd.).
The Y value of the color system was measured. Example 1 80 parts by weight of unpurified bromostyrene, divinylbenzene (manufactured by Dow Chemical Company, product “DVB-
20 parts by weight of "HP" (purity 80%) were mixed well to form a homogeneous liquid.Add a disperse dye to this monomer mixture.
Dianix BlueKR−FS1.1ppm, and Dianix
Violet3R-FS9.9ppm (all manufactured by Mitsubishi Chemical Industries, Ltd.) was added and mixed well. Then, as a polymerization initiator, tert.-butylperoxyisobutyrate 0.1
% by weight and 0.1% by weight of tert.-butylperoxyisopropyl carbonate were added and mixed well.
This liquid mixture was degassed under reduced pressure while being cooled with ice water, and then poured into a mold consisting of a lens molding die with a diameter of 75 mm and a polyethylene gasket, and cast polymerization was performed. The polymerization reaction started at 40°C, and the temperature was raised stepwise to 120°C, and the polymerization was completed over 30 hours. The obtained lens was colorless and transparent, had a refractive index nd of 1.62, and an Atsbe number of 30.
The obtained lens was subjected to an accelerated weather resistance test using a fade meter for 100 hours, but the progress of coloring was slight and it was sufficiently usable for practical use. Other physical properties are shown in Table 1. Example 2 In Example 1, Dianix was used as a disperse dye.
Instead of BlueKR-FS and Dianix Violet3R-FS, it consists of a pure pigment component that does not contain a dispersant.
A lens was molded according to Example 1, except that PTB-31 (CI number Disperse-26) at 0.07 ppm and PTV-57 (CI number Disperse-31) were used. The obtained lens was colorless and transparent, had a refractive index nd of 1.62, and an Atsbe number of 30. 100 by Fatemeter
Even after the accelerated weathering test for several hours, the progress of coloring was slight and was sufficient for practical use. Other physical properties are shown in Table 1. Comparative Example 1 A monomer was prepared and a lens was molded in the same manner as in Example 1 except that the disperse dye was omitted. Although the obtained lens was transparent, it was clearly colored pale yellow, and its appearance quality was at a level that could not be used for practical use as it was. Other physical properties are shown in Table 1. Example 3 2,2-bis(4-methacryloxyethoxy-
60 parts by weight of 3,5-dibromophenyl) propane, 20 parts by weight of divinylbenzene (manufactured by Dow Chemical Company, product "DVB-55" purity 60%) and 20 parts by weight of chlorstyrene (ortho/para = 65/35) After mixing thoroughly and dissolving at 60°C, the temperature was returned to room temperature. Dianix BlueKR− is added to this mixture as a disperse dye.
FS0.8ppm and Dianix Violet3R−FS7.2ppm
(both manufactured by Mitsubishi Chemical Industries, Ltd.) were added and mixed well. Next, 0.1% by weight of diisopropyl peroxydicarbonate and di-tert.
- 0.1% by weight of butyl peroxide was added, well mixed coating and poured into a lens mold similar to Example 1. The polymerization reaction was carried out by gradually raising the temperature from 50°C to 100°C over 40 hours. The obtained lens is colorless and transparent.
The refractive index nd was 1.62 and the Atsbe number was 31. Other physical properties are shown in Table 1. Examples 4 to 6 The same monomers as in Example 3 were used, and other disperse dyes were used under the same molding conditions. The experimental results are summarized in Table 1. Comparative Example 2 Same as Example 3 except that the disperse dye was removed.
A monomer was prepared according to Example 3, and a lens was molded. Although the obtained lens was transparent, it had a tendency to be colored pale yellow, and its appearance quality was at a level that could not be used for practical use as it was. Table 1 shows other physical properties.
Shown below. Example 7 Hexamethylene diisocyanate 5.0 parts by weight 2
-(4-acryloxyethoxy-3,5-dibromophenyl)2-(4-hydroxyethoxy-3,
0.01 weight of dibutyltin dilaurate as an NCO-OH reaction catalyst is added to a mixed solution consisting of 45.0 parts by weight of 5-dibromophenyl) propane and 50 parts by weight of divinylbenzene (manufactured by Dow Chemical Company, product "DVB-55" purity 60%). %, and Dianix as disperse dye
BlueB−SE2ppm, Dianix Violet3R−FS8ppm
(both manufactured by Mitsubishi Chemical Industries, Ltd.) were added and mixed well. Then, 0.1% by weight of di-tert.-butyl peroxide and 0.05% by weight of diisopropyl peroxydicarbonate were added as polymerization initiators and mixed well. This preparation was cooled with ice water and degassed under reduced pressure, then poured into a mold consisting of a lens molding die with a diameter of 75 mm and a polyethylene gasket, and cast polymerization was performed. It was heated initially at 50°C for 5 hours, then at 90°C for 11 hours, at 100°C for 5 hours, and at 120°C for 5 hours. After polymerization,
After gradual cooling, the polymer was removed from the mold. The obtained lens was colorless and transparent, had a refractive index nd of 1.61, and an Atsbe number of 32. The above lens was subjected to an accelerated weather resistance test using a fade meter for 100 hours, but the progress of coloring was slight and it was sufficiently usable for practical use.
Other physical properties are shown in Table 1. Example 8 In Example 7, Dianix was used as a disperse dye.
Dark BlueB−SE and Dianix Violet3R−FS
Instead, it consists of pure pigment ingredients that do not contain dispersants.
PTB-31 (CI number Disperse Blue-26)
0.05ppm and PTV−57 (CI number Disperse
A lens was molded according to Example 1, except that Violet-31) 0.45 ppm (all manufactured by Mitsubishi Chemical Industries, Ltd.) was used. The obtained lens is colorless and transparent, with a refractive index of
nd was 1.61 and Atsube's number was 32, and even after a 100-hour accelerated weathering test using a fade meter, the progress of discoloration was slight and was sufficiently usable for practical use. Also
Even after heating at 130°C for 2 hours, almost no coloring progressed. Comparative Example 3 Same as Example 7 except that the disperse dye was removed.
A monomer was prepared according to Example 7 and a lens was molded. Although the obtained lens was transparent, it was colored pale yellow to yellow, and its appearance quality was insufficient for practical use as it was. In a 100-hour accelerated weathering test using a fade meter, it was clearly colored yellow, and
After heating at 130°C for 2 hours, clear coloring was observed. Other physical properties are shown in Table 1.

[Table] [Effects of the Invention] The present invention relates to a plastic lens containing a disperse dye that has a complementary color relationship with the lens color tone (the color tone when no dye is included), and the lens obtained by the present invention is Color tone is significantly improved. In particular, when manufacturing plastic lenses with a high refractive index, organic compounds containing halogen elements or aromatic rings that are sensitive to heat and light (easily colored) are often used as monomers; In this case, the effects of the present invention are significantly exhibited. Furthermore, even when the obtained lens is left under heating or under ultraviolet rays such as when exposed outdoors, it has a color tone stabilizing effect.

Claims (1)

[Scope of Claims] 1. A high refractive index plastic lens made of a polymer crosslinked with a radically polymerizable polyfunctional organic vinyl monomer containing an aromatic ring and having a refractive index nd of 1.50 or more, which is made from among blue dyes. It is characterized by being substantially colorless because it contains a dye that is a complementary color to the color tone of the lens, which is a mixture of a selected dye and a dye selected from red and violet dyes. High refractive index plastic lens. 2. A high refractive index plastic lens according to claim 1, wherein the dye is a disperse dye. 3. The high refractive index plastic lens according to claim 1, wherein the amount of dye added is 0.01 to 100 ppm.