JPS6281601A - High refractive index plastic lens and its production - Google Patents

Abstract

PURPOSE:To obtain a plastic lens having good transparency and color tones and a high refractive index by using a specific crosslinked structure formable org. compd. as an essential component, adding a dye having a complementary color relation with the lens color tone to said compd. and polymerizing the same. CONSTITUTION:The dye having the complementary color relation with the color tone of the high refractive index plastic lens having >=1.50 refractive index nd and essentially consisting of the crosslinked structure formable org. compd. is added to the compsn. for producing said lens and the compsn. is polymerized. A radically polymerizable multifunctional org. vinyl monomer contg. an arom. ring is effective as the compd. having such high refractive index and crosslinked structure characteristic and further such vinyl monomer is more preferable if said monomer contains halogen elements except fluorine. A disperse die is preferable as the dye to be added to the compsn. for the purpose of improving the color tone and is preferably used at about 0.01-100ppm. The color tone of the plastic lens having the particularly high refractive index is thereby improved and the resulted lens has the stable color tone effect even if the lens is left standing under heating or UV rays such as outdoor exposure.

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, and a method for manufacturing the same.

[Prior Art] Plastic lenses have become popular in place of glass lenses as eyeglass lenses. Plastic lenses have advantages over glass lenses, such as being lighter, easier to dye, impact resistance, and easier to process.
Resin etc. are used. Among these, polydiethylene glycol bisallyl carbonate resin, which is a thermosetting resin, is particularly suitable for vision correction lenses because it is lightweight.
It is widely used because it has many advantages such as safety, particularly excellent impact resistance, and good cutting and polishing workability.

However, polydiethylene glycol biallyl 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 resins for high refractive index plastic lenses have been proposed.

Generally, in order to obtain a resin with a high refractive index, monomers are
It is effective to contain an aromatic ring, (1) contain a halogen element other than fluorine, and (2) contain a metal salt. By the way, regarding ■, there is a problem that the original lightweight characteristic of plastic lenses is lost, so aromatic vinyl monomer,
Alternatively, it is common practice to use a nuclear halogen-substituted aromatic vinyl monomer using a combination of (1) and (2).

For example, as an example of (1), Japanese Patent Publication No. 58-17527 describes that a copolymer of bisphenol A dimethacrylate and styrene gives a refractive index of 1.588; is bisphenol A
It is described that a copolymer of diacrylate having a bisphenol A group and bisphenoloxyethyl acrylate gives a refractive index of 1.600, and JP-A-59-191708 describes a copolymer of diacrylate having a bisphenol A group and diallylisophthalate. The copolymer mainly composed of
It is described to give a refractive index of 5 to 1.57.

An example of using ■ and ■ together is
No. 9 describes that a copolymer of diacrylate and styrene having a tetrabromobisphenol A group gives a refractive index of 1.590, and JP-A-59-8709
The publication describes that a copolymer of tetrabromoterephthalic acid diallyl ester and phenyl methacrylate gives a refractive index of 1.591, and also JP-A No. 60-12
No. 501 discloses a copolymer of tetrachlorophthalic acid diallyl ester and monochlorostyrene with a molecular weight of 1.600 to 1.600.
It is described that it gives a refractive index of 609.

By the way, it is a well-known phenomenon that compounds with a military double bond, represented by an aromatic ring, are sensitive to heat or light.In fact, when polymerizing compounds containing an aromatic ring,
There is a problem in that coloring tends to progress depending on the type and amount of peroxide used as a polymerization initiator, or heating conditions. Furthermore, if the obtained lens molded body is left under ultraviolet light such as when exposed outdoors, there is a problem in that the coloration increases.

On the other hand, organic compounds containing halogens also tend to be liberated by heat or light such as ultraviolet rays, causing problems with coloration. 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.

Regarding this development and analysis, please refer to J, ADI) 1. POI
m, sci.

It is detailed in Dan 463 (197B) etc. In reality,
This has been countered by adding excessive amounts of antioxidants, ultraviolet absorbers, etc. during polymerization, but a decline in polymerization formability was unavoidable, and the transparency and color tone of the molded products were not necessarily sufficient. .

[Problems to be Solved by the Invention] In order to manufacture a plastic lens with a high refractive index, as mentioned above, a polyfunctional organic compound containing an aromatic ring is used or a nuclear halogen element other than fluorine is used. Although it is effective to use polyfunctional organic compounds containing aromatic rings, they are sensitive to heat, light, etc., and have the problem of being easily colored during polymerization or when exposed outdoors.

The purpose of the present invention is to solve such problems, not only in terms of refractive index, transparency, and color tone, but also in terms of mechanical properties (rigidity, impact resistance).
Another object of the present invention is to provide a method for manufacturing a high refractive index plastic lens that also has excellent heat resistance.

Another object of the present invention is to provide a method for producing a high refractive index plastic lens that is resistant to coloring even when left under ultraviolet light such as heating or outdoor exposure.

"Means for Solving the Problems" The present inventors have conducted intensive research on a method of manufacturing a high refractive index plastic lens that solves the above problems, and as a result, have arrived at the present invention.That is, the present invention has the following configuration. Become.

(1) A high refractive index plastic lens made of a polymer having a refractive index nd of 1.50 or more and having a crosslinked structure, characterized by containing a dye having a complementary color relationship with the color tone of the lens. High refractive index plastic lens.

(2) In manufacturing a high refractive index plastic lens which has a refractive index nd of 1.50 or more and is mainly composed of an organic compound capable of forming a crosslinked structure, a dye having a color tone complementary to that of the lens is added. A method for producing a high refractive index plastic lens characterized by polymerization. ” The high refractive index plastic lens with excellent color tone of the present invention is
It is particularly effective when the refractive index nd is 1.50 or more and the crosslinked structure-forming organic compound is a radically polymerizable polyfunctional organic vinyl monomer containing an aromatic ring. When the radically polymerizable polyfunctional organic vinyl monomer containing halogen elements other than fluorine contains a halogen element other than fluorine, more favorable effects are exhibited. When a disperse dye is used as the dye used to improve the color tone of the present invention,
Not only the lens during molding, but also the lens under heating or
It is characterized in that it provides better effects even when left under ultraviolet light such as when exposed outdoors.

Of course, the production method of the present invention can also be favorably applied to the case of using a vinyl monomer having no aromatic ring or halogen, such as diethylene glycol bisallyl carbonate.

In the present invention, examples of organic compounds having a refractive index nd of 1.50 or more and capable of forming a crosslinked structure include the following polyfunctional organic vinyl monomers containing an aromatic ring and capable of radical polymerization.

Terephthalic acid bisallyl ester, isophthalic acid bisallyl ester, trimellitic acid triallyl ester, terephthalic acid bis(aryloxycarbonylmethyl) ester, 5,5゛-dimethylbiphenyl-3,3゛-dicarboxylic acid allyl ester, 1, Polyvalent allyl esters such as 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 carbonate, 4,4-diphenylsulfone bisallyl carbonate, 1,3-bis(hydroxyethoxy)benzene bisallyl carbonate, 1,4-bis(hydroxyethoxy) ) Benzene bisallyl 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-bis(hydroxyethoxy)
naphthalenebisallylcarbonate-1,4,4-bis(
Hydroxyethoxy 2) Polyvalent allyl carbonates such as diphenylpropane bisallyl carbonate, 4.4”-bis(hydroxyethoxy)diphenylsulfone bisalcarbonate, 1,4-diacryloxybenzene, 1
．． 4-dimethacryloxybenzene, 1,4-diacryloxyethoxybenzene, 1,4-dimethacryloxyethoxybenzene, 1,5-diacryloxynaphthalene, 1
゜5-dimethacryloxinaphthalene, 1,5-bis(β
-acryloxyethoxy)naphthalene, 1,5-bis(
β-methacryloxyethoxy)naphthalene, 2°2°-
Bis-acryloxybiphenyl, 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-bis(4-methacryloxyphenyl)propane,
-methacryloxyethoxy)phenylpropane, 2,2
-Bis(4-acryloxyboriethoxyphenyl)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) and phenyl, 2,2-bis(3-acryloyl-2-hydroxypropoxyphenyl)propane, 2,
Examples include polyvalent (meth)acrylates such as 2°-bis(3-methacryloyl-2-hydroxypropoxyphenyl)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-acryloxyethoxy-3,5-dibromophenyl)propane, diallyl phthalate, diallyl isophthalate, 2,2-bis(4-methacryloxyethoxy-3,5-dibromophenyl)sulfone, 2,2
-bis(4-acryloxyethoxy-3,5-dibromophenyl)sulfone, tetrabromophthalic acid diallyl ester, tetrabromoterephthalic acid diallyl ester, and the like.

In addition, in the present invention, the organic compound having a refractive index nd of 1.50 or more and capable of forming a crosslinked structure may be a monomer having one radically polymerizable double bond within the molecule. In those containing functional groups such as 10H1-NCOl-COOH, -NH2, and epoxy groups, monomer compounds containing multiple double bonds obtained by intermolecular bonds mediated by the functional groups are used. It can be used alone or in combination with the various monomers mentioned above.

Such monomer compounds include an addition reaction product in which 2 moles of 1-vinyl-4-hydroxybenzene is reacted with 1 mole of hexamethylene diisocyanate, and an addition reaction product in which 2 moles of bisphenol A monoacrylate and 1 mole of xylylene diisocyanate are reacted. Things, methacrylic paste 2
mol of 2,2-bis(4-glycidoxyphenyl)propane, an addition reaction product of 1 mol of 4-hydroxyphenyl methacrylate, 1 mol of glycidyl methacrylate, vinyl acetic acid 2
1 mole of xylylenediamine can be used.

In the present invention, a monofunctional monomer having a radically polymerizable double bond is added in addition to the crosslinking polyfunctional monomer, depending on the degree of various properties desired for the eyeglass lens. You can also do that. Such monomers include styrene, monochlorostyrene, dichlorostyrene, monobromostyrene, dipromostyrene, phenyl acrylate,
Phenyl methacrylate, monochlorophenyl acrylate, monochlorophenyl methacrylate, dichlorophenyl acrylate, dichlorophenyl methacrylate,
Trichlorophenyl acrylate, trichlorophenyl methacrylate, monobromophenyl acrylate, monobromophenyl methacrylate, dibromophenyl acrylate, dibromophenyl methacrylate, tribromophenyl acrylate-1-, tribromophenyl methacrylate, pentabromophenyl methacrylate, pentabromophenyl methacrylate , monochlorophenoxyethyl acrylate-1~, monochlorophenoxyethyl methacrylate, dichlorophenoxyethyl acrylate, dichlorophenoxyethyl methacrylate, trichlorophenoxyethyl acrylate, trichlorophenoxyethyl methacrylate, monobromophenoxyethyl acrylate, monobromophenoxyethyl methacrylate, dibromophenoxyethyl acrylate,
Dibromophenoxyethyl methacrylate, tribromophenoxyethyl acrylate, tribromophenoxyethyl methacrylate, pentabromophenoxyethyl acrylate, pentabromophenoxyethyl methacrylate, benzyl acrylate, benzyl methacrylate-1~, bromobenzyl acrylate, dibromobenzyl acrylate, α - Naphthyl acrylate, α-naphthyl methacrylate, β-naphthyl acrylate, β-naphthyl methacrylate, ethyl acrylate-1~, ethyl methacrylate, tribromopentyl acrylate, 1
Examples include helibromopentyl methacrylate-1-2,3-dibromopropyl acrylate, phenyl acrylic carbonate, benzyl allyl carbonate 1-1 allyl benzoate, allyl naphthalene carboxylate, and halogen-substituted products thereof.

The composition ratio of the crosslinking polyfunctional monomer, which is an essential component in the present invention, and the above-mentioned -functional monomer is determined by the optical properties, mechanical properties, thermal properties, etc. required for the desired eyeglass lens. However, it is preferable that the amount of the crosslinking polyfunctional monomer, which is an essential component in the present invention, be 5% by weight or more, preferably 1% 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 a dye containing at least one azo group, anl-laquinone groove structure, condensed polycyclic quinone, or heterocycle in one molecule, in addition to commercially available synthetic dyes, and is an industrial dye. Those used as upper disperse dyes can be used.

To illustrate these disperse dyes, as a blue dye, D
ianix Blue series (B-3E, KR-FS
, RC-E, RN-E, AC-E, EB-E.

KB-FS, E3G-FS, HB-FS, KG-3E,
GR-E, (Mitsubishi Chemical Industries product) ) ,) liket
.

n Polyester Blue series (GFL,
SG, 3G.

BLN, BCL, DingGSF, GRN, (Mitsui Toatsu Chemical Co., Ltd. product)), ayalon po+yester Blu
e series (GRF, 30F, GGF, BBF, TSF
, RGF (Nippon Kayaku Co., Ltd.)), Sumikaron
Dianix Re is a red dye such as the Blue series (GG, BR, R, BG, (Sumitomo Chemical)).
d series (R-E, 3G-FS, G-3E, BG-F
S, FL-FS, U-8E, AC-E, BN-3E, B
-FS, KB-3E, (Mitsubishi Chemical Corporation product) ), H
iketon Poyester Red series (
FB, FL, 2BSF, FN, (Mitsui Toatsu Chemical products)
), Kayal.

n Polyester Red series (Rubin
e-FSF, BR3F, BSF, LSF, 2BSF
(Nippon Kayaku Co., Ltd. product) ), Sumikaron Red
Series (3G, FB.

3BR, BGS, B, G, 2gs, (Sumitomo Chemical product))
Examples of purple dyes include Dianix Violet series (5R-3E, 3R-FS, 2R-E (products of Mitsubishi Chemical Industries)), Miketon Polyest
er Violet series (BN, FR (Mitsui Toatsu Chemical Co., Ltd. product)), ayalon Poyester V
iolet series (BNF, RNF (Nippon Kayaku Co., Ltd. product)
＞ , Sumikaron Violet 1. J-
Examples include RR, R, R3 (Sumitomo Chemical Co., Ltd.).

To carry out the present invention, a disperse dye having a complementary color tone to the color tone of the upper layer is added to the seven dyes (single or a mixture) prepared for lens molding, and mixed well. Normally, a blue-violet disperse dye is selected when the lens molding has a yellow tone, but red and blue disperse dyes can be combined to form a mixed dye with the desired complementary color relationship. It is also possible to use The amount of the disperse dye added is determined by the fact that the coloring of the lens molding pads disappears by adding the dye. Changes in color tone can be easily observed by visual observation, but C
By measuring the x and y values of the IE (International Commission on Illumination Q) color system, slight changes in color tone can be detected and dye addition can be easily controlled. The amount of dye added is generally 0.
．． 001 to 11000pp, preferably 0.01
~1100 ppm. If it is less than 0.01pf)m, the effect of improving the color tone is poor, and if it exceeds 11001)p, the color of the dye becomes dominant and the decrease in transmitted light becomes noticeable.
The function as a spectacle lens deteriorates. Lens molding is mainly performed by cast polymerization. Depending on the selection of polymerization conditions, the molded lens may be colored even if a colorless lens circumferential knob is used. 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, but depending on the degree of the desired lens color tone, , a complementary color effect is realized by adding a disperse dye in a complementary color to the lens color tone, which cancels out the lens color tone.
It is also possible to make 1q of bluish glass-like lenses. The presence of a disperse dye in a lens can be analyzed using spectroscopic techniques such as a U spectrum and a fluorescence spectrum.

For polymerization, known radical polymerization methods, photopolymerization methods, etc. can be employed. That is, the above monomer may be used alone or in combination with the various monomers mentioned above.
After mixing the components, a polymerization initiator such as diisopropyl peroxydicarbonate, similystyl peroxydicarbonate, tert-butyl peroxyvivalate, lauroyl peroxynide, tert-butyl peroxyisobutyrate, tert-butyl About 0.01 to 10 parts by weight of peroxyisopropyl carbonate, ditertiary butyl peroxide, benzoyl peroxide, azodiisobutyronitrile, azovistachary-octane, etc. are mixed with 100 parts by weight of the monomer. The resulting mixture is poured into a tightly prepared mold and gradually heated to complete the 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, composition ratio, and selection of polymerization initiator, so they cannot be fixed uniformly, but the polymerization is generally completed at 40 to 150'C over 1 to 100 hours. is preferable.

Further, the resin of the present invention can also be produced using a photopolymerization method. That is, after using the above monomers alone or after mixing the above various monomers, a photosensitizer such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzophenone, 2-hydroxy-2-methyl-propiophenone, 0.01 to 10 parts by weight of benzyl dimethyl ketal, benzoin isopropyl ether, acel-phenone, dimethoxyacetophenone, 1-taloloane l-laquinone, 1,4-naphthoquinone, etc. are mixed with 100 parts by weight of the monomer, Polymerization is carried out by irradiation with ultraviolet lamps, mercury lamps, 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 according to the present invention, in addition to the above-mentioned essential ingredients, additives such as antistatic agents, anti-coloring agents, surface smoothing agents, ultraviolet absorbers, and antioxidants are required. 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. , fluorine-based surfactants, surfactants, etc.; UV absorbers include 2-(hydroxy-5-methylphenyl)benzotriazole, 2-(hydroxy-5-tert-butylphenyl)benzotriazole, 2- (3°, 5-ditertiary-butyl-
2-hydroxyphenyl)-benzotriazole, 2-
Hydroxy-4-n-octoxybenzophenone, etc.
As the anti-cleavage agent, hindered phenol, hindered amine, etc. can be added.

The plastic lens of the present invention is anti-reflective, has high hardness,
In order to perform surface modification such as improving wear resistance, chemical resistance, and imparting antifogging properties, it is possible to apply 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 create fashionable properties. 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 Atzbe number Measured at 20'C using a Pulfrich refractometer. The wavelength is the value at the D line of 58,929 people.

(2) Total light transmittance The total light transmittance of the lens molded product was measured using a color computer (Model 5M-3, Suga Test Instruments Co., Ltd.) using CIE (
The Y value of the color system (International Commission on Illumination) was measured to determine the transmittance.

(3) The color tone of the colored lens molded product is checked using a color computer (model 5M-).
3. Using YI of CIE color system (Suga Test Instruments Co., Ltd.)
The value was measured.

Example 1 80 parts by weight of unpurified bromostyrene, divinylbenzene (manufactured by Dow Chemical Company, product "'DVB-HP" purity 8)
0%) were thoroughly mixed to form a homogeneous solution. Add DianixBlueKR as a disperse dye to this Nanatsuma mixture.
-FS 1.11)l)m, and DianixVi
olet 3R-FS 9.9DDm (all manufactured by Mitsubishi Chemical Industries, Ltd.) was added and mixed well. Then, as polymerization initiators, 1 to 0.1% by weight of tert, -butylperoxyisobutylene and 1 to 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 made of a lens molding die with a diameter of 75 mm and polyethylene gaskets 1 to 1 for cast polymerization.

The polymerization reaction was started at 40°C, and the temperature was raised stepwise to 120°C, taking 30 hours to complete the polymerization. The obtained lens was colorless and transparent, had a refractive index nd of 1.62, and an arahe number of 30. The obtained lens was subjected to a 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 Bl was used as a disperse dye.
ue KR-FS and Dianix Violet
3 Instead of R-F S, P-cho B-31 (CI number 〇1sperse
-26)0. A lens was molded according to Example 1, except that O7ppm and PTV-57 (CI number D 1sperse-31) were used. The obtained lens was colorless and transparent, had a refractive index nd of 1.62, and an arahe number of 30. A 100-hour accelerated weathering test using a fade meter showed that 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 the appearance quality was at a level that it could not be used for practical use as it was. Other physical properties are shown in Table 1.

Example 3 2.2-bis(4-methacryloxy1-xy-3,5
- dibromophenyl) propane 60 parts by weight divinylbenzene (manufactured by Dow Chemical Company, product "D V B -
Mix well with 20 parts by weight M of 55'' 60%) and 201 parts of chlorstyrene (ortho/para-65/35)
After dissolving at 60'C, the temperature was returned to room temperature.

Add Dianix Blue as a disperse dye to this mixture.
KR-FSo, 8ppm and Dianix Viol
et 3 R-F S7, 2 ppm (all manufactured by Mitsubishi Chemical Industries, Ltd.) was added and mixed well. Then, diisopropyl peroxydicarbonate 1-0.
Example 1
It was injected into a lens mold similar to the one above.

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, and has a refractive index n
d was 1.62 and Atsbe's number was 31. Other physical properties are shown in Table 1.

Examples 4 to 6 The same monomers and disperse dyes as in Example 3 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.
Seven lenses were prepared and lenses were molded according to the method. 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. Other physical properties are shown in Table 1.

Example 7 Hexamethylene diisocyanate 5.0 parts by weight 2-(4
-acryloxyethoxy-3,5-dibromophenyl)
A mixed solution consisting of 45.0 parts by weight of 2-(4-hydroxyethoxy-3,5-dibromophenyl)propane and divinylbenzene (manufactured by Dow Chemical Company, product "DVB-55" purity 60%>50 parts by weight) , 0.01% by weight of dibutyltin dilaurate as NGO-OH reaction catalyst,
and Dianix Blue B-3 as a disperse dye.
E 2ppmm, Dianix Violet3
8 ppm of R-F S (all manufactured by Mitsubishi Chemical Industries, Ltd.) was 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 degassed under reduced pressure while being cooled with ice water, and 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 completion of polymerization, the polymer was gradually cooled and taken out from the mold. The obtained lens was colorless and transparent, had a refractive index nd of 1.6L, and an Abbé number of 32. The above lens was subjected to a 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 Da was used as a disperse dye.
rk BlueB-S E and Dianix Vi
Instead of olet 3 R-F S, PTB-31 (CI number Dis
perse Blue-26)0.051)E)Ill
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 was colorless and transparent, had a refractive index nd of 1.6L, and an Abbé number of 32. Even after a 100-hour weather resistance test using a fade meter, the progress of coloring was slight and it was sufficiently usable for practical use. Also 130'
Even after heating at C for 2 hours, almost no coloring progressed.

Comparative Example 3 Same as Example 7 except that the disperse dye was removed.
Seven lenses were prepared and lenses were molded according to the method. 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 clearly colored when heated at 130° C. for 2 hours. Other physical properties are shown in Table 1.

[Effects of the Invention] The present invention is a manufacturing technology for plastic lenses 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 lenses obtained by the present invention have significantly improved color tone. be done.

Especially when manufacturing plastic lenses with a high refractive index, the monomer is sensitive to heat and light (easily colored).
Microscopic compounds containing halogen elements and aromatic rings are often used, and the effects of the present invention are significantly exhibited in producing such lenses. 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 (5)

[Claims] (1) A high refractive index plastic lens made of a polymer having a refractive index nd of 1.50 or more and having a crosslinked structure, characterized by containing a dye having a complementary color relationship to the color tone of the lens. High refractive index plastic lens. (2) In manufacturing a high refractive index plastic lens which has a refractive index nd of 1.50 or more and is mainly composed of an organic compound capable of forming a crosslinked structure, a dye having a color tone complementary to that of the lens is added. A method for producing a high refractive index plastic lens characterized by polymerization. (3) The refractive index nd is 1.50 or more, and the crosslinked structure-forming organic compound is a polyfunctional organic vinyl monomer containing an aromatic ring and capable of radical polymerization.
2) A method for producing a high refractive index plastic lens as described in section 2). (4) The method for manufacturing a high refractive index plastic lens according to claim (2), wherein the dye is a disperse dye. (5) The method for manufacturing a high refractive index plastic lens according to claim (2), wherein the amount of dye added is 0.01 to 100 ppm.