JPH0797410A - Production of resin for high refractive index lens - Google Patents

Abstract

PURPOSE:To obtain a resin for a lens having excellent processability and optical homogeneity and a high refractive index by copolymerizing triphenylvinylsilane and/or diphenylvinylsilane with a specified radical-polymerizable monomer. CONSTITUTION:At least either triphenylvinylsilane or diphenylvinylsilane is copolymerized with at least one radical-polymerizable monomer which can give a homopolymer of a refractive index of 1.55 or above. 3-40wt.%, desirably 7-30wt.% at least either triphenylvinylsilane or diphenylvinylsilane is mixed with 0-70wt.% at least either diallyl isophthalate or diallyl terephthalate and 0-40wt.% at least anothet radical-polymerizable monomer which can give a homopolymer of a refractive index of 1.55 or above, and the resultant mixture is subjected to copolymerization.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION The present invention provides copolymerization of a specific monomer having a silicon atom in the molecule,
The present invention relates to a method for producing a new resin for a high refractive index lens.

[0002]

2. Description of the Related Art As a thermosetting resin for lenses, a resin obtained by casting polymerization of diethylene glycol bisallyl carbonate has been used for a long time, but its refractive index N _D is 1.
50 and the refractive index N _D 1.5 of the crown glass lens
It is lower than 2 to 1.53, and the lens using this resin has a drawback that the thickness rapidly increases as the number of altitudes increases.

[0003] Thermoplastic resins, high refractive index as polystyrene and polycarbonate _(N D _1.58~
1.59), but they are fusible, soluble, and plastic and therefore unsuitable for the following applications. That is, when framing like a spectacle lens, it is necessary to cut and polish the periphery of the lens, and it is tightened by a spectacle frame. Furthermore, one side of a semi-finished lens is rubbed to make a lens of a special power. It is not suitable for operations such as high-speed cutting and polishing with a processing machine, and it must be a thermosetting resin.

Based on such thinking, many studies have been conducted on the development of thermosetting resin for high refractive index lenses,
Many patent applications have been filed. Among them, what is currently regarded as important is one having a refractive index N _D in the vicinity of 1.59 to 1.60, which includes bisphenol A or a similar compound containing 2 or more halogens, especially bromine atoms. In particular, a high-refractive-index resin whose main component is a monomer having a skeleton obtained by adding 4 units. (Japanese Patent Publication No. 62-25162, Japanese Patent Publication No. 2-15841, Japanese Patent Publication No. 3)
-19521, Japanese Patent Publication No. 3-20721) A high refractive index resin obtained by mainly utilizing a reaction (urethane forming reaction) between an isocyanate compound and a hydroxyl compound or a thiol compound. (JP-A-57-136601, 57-136602, 5)
9-133211, 60-11513, 60-24
9101, 62-73201, 64-26622,
64-54021, JP-A-1-185501, 2-
153302)).

Further, a technique attracting attention for a material having a refractive index N _D in the vicinity of 1.56 to 1.57 (herein referred to as a quasi high refractive index resin) is a quasi high refractive index resin containing diallyl phthalates as a main component. . (Japanese Patent Publication 57-42841, Japanese Patent Publication 60-4432)
7, refer to Japanese Patent Publication No. 2-39761)) Bisphenol A as it is or by adding 4 mol or less of ethylene oxide thereto, and changing the phenolic OH groups to alcoholic OH groups as much as possible, and then converting to acrylic acid or methacrylic acid ester. A semi-high refractive index resin whose main component is a monomer. (See Japanese Patent Publication 58-17527).

[0006]

When producing a resin for a high refractive index lens, the desirable matters are, from the viewpoint of raw materials,
It should be easily available, or the raw materials should be easily synthesized and purified. From the viewpoint of resin quality, it should be colorless and transparent, have optical homogeneity, impact resistance, light resistance and various processability. In terms of factory work, manufacturing operating conditions are not harsh (for example, there are no difficult conditions such as using extremely low or high temperatures, and slight temperature errors are not allowed), and easy release and high yield. Is easy to obtain.

The above-mentioned techniques (1) and (2) satisfy almost all of these desirable requirements except that they have a quasi-high refractive index, whereas the technique (2) requires the cost of producing and purifying the monomer. The problem is that the resin is expensive and the impact resistance and light resistance of the obtained resin are insufficient, and in the case of, the technology has not been solidified yet and the operating conditions are severe, so the yield has reached a satisfactory point. The problem is not. It improves that the therefore and techniques not obtained only sub-high refractive index, if it was possible to increase the high refractive index (around N _D from 1.59 to 1.60), say to give the most desirable method obtain. The present inventors have conducted extensive research to obtain the most desirable method, and arrived at the present invention.

That is, the present invention comprises one or two members of the group consisting of triphenylvinylsilane and diphenyldivinylsilane, and one or more radically polymerizable monomers having a homopolymer refractive index of 1.55 or more. A method for producing a resin for a high refractive index lens, characterized in that the first monomer is triphenylvinylsilane and diphenyldivinylsilane. 40% by weight, preferably 7-30% by weight,
One or two members of the group consisting of diallyl isophthalate and diallyl terephthalate are used as the second monomer in an amount of 20 to 20.
70% by weight, and as a third monomer, 0 to 40% by weight of one or more other radically polymerizable monomers having a homopolymer refractive index of 1.55 or more are mixed and copolymerized. And a method for producing a resin for a high refractive index lens.

Here, the synthetic methods of both silanes used in the present invention are listed. a) Synthetic method of triphenylvinylsilane: It can be synthesized by using the Grignard reaction. As an example, using sufficiently purified tetrahydrofuran as a solvent, vinylmagnesium bromide is allowed to act on triphenylchlorosilane or triphenylsilane, decomposed with a saturated aqueous solution of ammonium chloride, and then triphenylvinylsilane dissolved in tetrahydrofuran is recovered. Then, it was purified by vacuum distillation in the presence of a polymerization inhibitor and a trace amount of nitrogen gas. It is a colorless and transparent liquid. (When triphenylsilane is used as the raw material, a small amount [for example, about 5 to 10%] of the raw material substance may remain in the synthesized triphenylvinylsilane, but this is substantially effective for the performance of the lens resin of the present invention. It has no effect.)

B) Method for synthesizing diphenyldivinylsilane
Similarly, it can be synthesized using the Grignard reaction. As an example, diphenyldichlorosilane is reacted with vinylmagnesium bromide in tetrahydrofuran, and after decomposition, diphenyldivinylsilane in tetrahydrofuran is recovered and purified by vacuum distillation in the presence of a polymerization inhibitor and a small amount of nitrogen gas. did. It is a colorless and transparent liquid.

Both of these silanes behave similarly to aromatic allyl compounds and have benzene nuclei, such as carboxylic acid allyl esters, acrylic acid esters and methacrylic acid esters, and also styrenes, divinylbenzenes and the like. It has good compatibility with, and when it is mixed with these and copolymerized, if the mixed composition and the polymerization conditions (the type and amount of the polymerization initiator, the polymerization temperature-time curve, etc.) are properly selected, the copolymer will be well copolymerized. We can make high quality resin for high refractive index lenses.

These two silanes may be used alone or simultaneously, and the total amount of the silanes used is 3% by weight of the total amount of the monomers, which is effective, but preferably 7 If it is more than weight%, the refractive index is obviously increased, and it can be seen that it is more effective. The maximum is 40% by weight. If it exceeds this value, the obtained resin may exhibit a decrease in rigidity at a high temperature, for example, around 100 ° C, which is unsuitable for a lens or the like that is dyed at around 100 ° C. Therefore, it is possible to prevent such a problem from occurring by preferably setting it to 30% by weight or less and by appropriately selecting the composition of the monomer mixture.

The second monomer diallyl isophthalate and diallyl terephthalate of claim 2 may be used alone or at the same time, but the reason for using this monomer is, as already mentioned, both silanes. This is because it has a structure similar to that of the above-mentioned compounds, has good compatibility, has a close polymerization rate, is relatively slow, and is easy to form an optically homogeneous lens, and has a good yield. When the amount of the second monomer used is less than 20% by weight of the total monomer mixture, the above characteristics are not exhibited, and when it exceeds 70% by weight, the first monomer
The amount of the monomer is reduced and a high refractive index cannot be obtained. Ie 20
This is the reason why it is set to 70% by weight.

The third monomer according to claim 2 is the first and second monomers.
It is intended to supplementarily improve the properties of a copolymer of monomers, and examples thereof include phenyl acrylate, phenyl methacrylate, benzyl acrylate, benzyl methacrylate, bisphenol S diacrylate, bisphenol S dimethacrylate, and 2,2. -Bis (acryloxy-polyethoxy-phenyl) propane [Note: polyethoxy is a polymerizing group of more than 4 mol and not more than 6 mol of ethylene oxide in total, the same applies hereinafter], 2,2-bis (methacryloxy-
Polyethoxy-phenyl) propane, styrene, α-methylstyrene, chlorostyrene, divinylbenzenes,
1,3,5-benzenetricarboxylic acid triallyl ester, 1,2,4-benzenetricarboxylic acid triallyl ester, benzoic acid allyl ester, o-phenylbenzoic acid allyl ester, p-phenylbenzoic acid allyl ester, biphenyl- 2,2'-dicarboxylic acid diallyl ester, bisphenol A diallyl carbonate, bisphenol S diallyl carbonate, o-phenylphenol allyl carbonate, p-phenylphenol allyl carbonate, benzyl methyl maleate, benzyl methyl fumarate and the like can be mentioned.

The amount of the third monomer used is 0 to 40% by weight based on the total monomer mixture. Among the third monomers exemplified above, many of acrylic compounds, methacrylic compounds, styrenes and divinylbenzenes have a higher polymerization rate than the first and second monomers, and they are all single monomers. 30% by weight or less based on the weight of the monomer mixture, preferably 20
It is necessary to use less than or equal to wt% to improve the copolymerizability.

Benzylmethyl maleate and benzyl methyl fumarate have a role of accelerating the polymerization of the allyl group, and it is usually effective to add only a few%, at most 10% by weight, and to add more than that. It causes harmful effects such as lowering the final polymerization degree. Although the aliphatic maleate and fumarate do not have a benzene nucleus, the addition of a small amount of about several% into the monomer mixture has the effect of accelerating the polymerization of the allyl group, and the addition of a small amount of the polymer causes Since the refractive index is rarely lowered, it may be added if necessary. In this case, diethyl and di-n-butyl derivatives are suitable.

When copolymerizing the above-mentioned monomer mixture, a radical polymerization initiator is used. This includes diisopropyl peroxydicarbonate, di-n-propyl peroxydicarbonate and dineopentyl purge carbonate, which act effectively at relatively low temperatures (about 30 to 50 ° C.), and medium temperatures (60 to 80). (Around ℃)
T-butylperoxypivalate, which works effectively in
-Butylperoxy-2-ethylhexanoate and t-butylperoxyisobutyrate, etc., which effectively act at relatively high temperatures (near 90 to 110 ° C) 1,
1-bis (t-butylperoxy) -3,3,5-trimethylcyclohexane, 1,1-bis (t-butylperoxy) cyclohexane and t-butylperoxy-
Suitable examples include 3,5,5-trimethylhexanoate.

These polymerization initiators may be used alone or in admixture of two or more. The amount used is required to be 0.5 to 8% by weight (total when two or more polymerization initiators are used) with respect to the total weight of the monomer mixture.

Since the resin for a high refractive index lens produced in the present invention places importance on light resistance, an ultraviolet absorber is added to the monomer mixture during the polymerization. 2- (3,5-
Di-t-butyl-2-hydroxyphenyl) benzotriazole, 2- [2-hydroxy-5- (1,1,3,3
3-tetramethylbutyl) phenyl] benzotriazole and other triazoles, or 2-hydroxy-4-
n-octoxybenzophenone, 2-hydroxy-4-
Good results may be achieved with benzophenone-based compounds such as benzyloxybenzophenone. That is, these ultraviolet absorbers are mixed in an amount of 0.05 to 2% by weight based on the total weight of the monomer mixture. This prevents yellowing and deterioration of physical properties due to aging under the irradiation of sunlight after molding into a lens, and especially when used as a lens for eyeglasses, it blocks ultraviolet rays as much as possible and helps to protect the eyes. To be

In the present invention, polymerization and molding are usually carried out by using two well-polished and surface-strengthened glass molds and a rubber-like elastic substance (chemically inert to monomers and the like). For example, through a gasket made of ethylene-butadiene copolymer, ethylene-vinyl acetate copolymer, etc.), the gaskets are assembled in parallel, and each of the above-mentioned monomers, polymerization initiators, and UV absorbers are arranged in the space. If necessary, the mixed solution of (a release agent, a yellowing complementary colorant, etc. may be added) is preliminarily polymerized and then injected. Here, the prepolymerization means that the mixed solution is slightly heated and stirred in advance in the presence of a small amount of a polymerization initiator to slightly increase the viscosity of the solution.
(Alternatively, one component or only a few components of the monomer mixture may be separately pre-polymerized and then mixed with other monomers. That is, block copolymerization is performed.) By doing so, It has an effect of preventing the mixed solution from leaking through the gap between the mold and the gasket, and at the same time, reducing adverse effects due to volume contraction during polymerization.

After the injection is completed, the material is placed in a heating furnace and polymerized.
The polymerization time is generally 10 to 30 hours, but 15
-20 hours is often suitable for the convenience of operation. As described above, the temperature of the heating furnace should be adjusted in consideration of the fact that the temperature at which it works effectively varies depending on the type of polymerization initiator. For example, when di-n-propylperoxydicarbonate, which acts effectively at a relatively low temperature as a polymerization initiator, is used alone, the temperature rising rate between 30 and 50 ° C. is made as slow as possible, and the maximum polymerization temperature is 90%. ~ 100
It should be kept at 0 ° C. and kept at temperature for 0.5 to 3 hours so that all of the initiator is decomposed without remaining in the polymer.

If, for example, Dyneopentyl Purge Carbonate which works effectively at a relatively low temperature as a polymerization initiator and t-butylperoxy-2-ethylhexanoate which works effectively at a moderate temperature are used at a relatively high temperature. When t-butylperoxy-3,5,5-trimethylhexanoate, which works effectively under
C., 60 to 80.degree. C., and 90 to 110.degree. C. in the respective temperature ranges, the heating rate is made as slow as possible, the heating rate in the middle between them is made relatively rapid, and the maximum polymerization temperature is set to 120.degree. The temperature should be maintained for 0.5 to 3 hours so as to decompose any excess polymerization initiator.

When the polymerization is completed, the polymer is released from the mold. Mold release is usually performed at a high temperature, but in some cases, it is better to perform at a low temperature. First remove the gasket,
The polymer is then mechanically removed from the mold. The polymer of the present invention can be released from the mold without using a special mold release agent. (The process from the injection of a mixed solution of monomers etc. into a mold to the release is called cast polymerization.)

After releasing the mold, heat treatment is performed. Normally, put in a heating furnace at a temperature 5 to 10 ° C higher than the maximum polymerization temperature and
Heat treatment is performed at the temperature for 0 minutes to 2 hours. This makes it possible to eliminate the internal strain of the polymer generated during the polymerization or the mold release. (It is necessary to perform the heat treatment even after the rough polishing of the next semi-finished lens and the subsequent polishing.)

The lens produced by the above operation can be put to practical use as a product as it is, but by casting polymerization, a semi-finished lens is first made, and the rear surface of this is rough-polished and polished to obtain the desired degree of product lens. Can also be It was confirmed that the polymerized molded product of the present invention is well suited for such rough sliding and polishing steps and can be made into an excellent product without melting or roughening of the polished surface.

The resin for lenses according to the production method of the present invention can be well dyed with a disperse dye in a dyeing bath at 80 to 95 ° C., and hard coatings such as organic and silicon-containing hard coatings can be strongly bonded. It was found that the solid deposition of SiO ₂ and metal oxide was basically possible in a vacuum deposition apparatus.

In order to describe the present invention more specifically and in detail, the following examples are shown. However, the present invention is not limited to these examples. The test methods for various physical properties shown in the examples are as follows. 1) Refractive index N _D : Measured using an Abbe refractometer.
Monobromnaphthalene was used as the contact liquid. 2) Abbe number ν _D : Same as above 3) Pencil hardness: Measured according to JIS (K5400). 4) Impact resistance: FD on resin plate for lens with thickness of 2mm
A steel ball drop test conforming to the A standard was carried out, and those that did not crack were rated good. 5) Light resistance: An irradiation test was carried out for 200 hours in an ultraviolet irradiation tester, and those having no coloring, that is, yellowing were regarded as good. (The polystyrene and polycarbonate tests carried out for comparison showed yellowing and were unsatisfactory.) 6) Dyeability: Dipping in a disperse dyeing bath at 90 ° C. for 15 minutes to see if dyeing to a medium density Tested and accepted what was possible.

[0028]

Example 1 A monomer mixture consisting of 25 parts by weight of triphenylvinylsilane, 50 parts by weight of diallyl isophthalate, 22 parts by weight of bisphenol S diacrylate and 3 parts by weight of benzylmethyl maleate was added to 2- [2 as an ultraviolet absorber. -Hydroxy-5- (1,1,3,3-tetramethylbutyl) phenyl] benzotriazole 0.3
2.5 parts by weight of t-butylperoxy-2-ethylhexanoate and t-butylperoxy-3,5,5 were added as a radical polymerization initiator to the solution.
-2.5 parts by weight of trimethylhexanoate were added and dissolved, and this mixture for polymerization was heated in a space formed by two surface-reinforced glass flat plate molds (distance 2 mm) and a gasket made of ethylene-butadiene copolymer. It was injected at that time and cast polymerization was carried out.

The temperature-time curve for cast polymerization is 55 ° C.
From 80 to 80 ° C with a gentle slope over 8 hours,
80 hours to 90 degrees Celsius in 1.5 hours The temperature rises rapidly from 90 degrees Celsius to 110 degrees Celsius over 5.5 hours with a gentle slope, and 110 degrees Celsius to 120 degrees Celsius in 1.5 hours The temperature was rapidly raised, and heating was continued at 120 ° C. for 1.5 hours to terminate the polymerization. When heated, the gasket was removed, and the resin plate was mechanically released from the two mold plates. Release was relatively easy. This resin plate was heat-treated at 125 ° C. for 1 hour to remove the internal strain. The heat-treated resin plate was colorless and transparent, and had a high refractive index and a low dispersion (ν _D 44). The test results are shown in Table 1.

[0030]

Example 2 Instead of the monomer mixture used in Example 1,
15 parts by weight of triphenylvinylsilane, 20 parts by weight of diphenyldivinylsilane, 40 parts by weight of diallyl terephthalate, 2,2-bis (methacryloxy-poly <4.5>
15 parts by weight of ethoxy-phenyl) propane [note: poly <4.5> ethoxy represents a total of 4.5 mol polymerizing groups of ethylene oxide], bisphenol S diacrylate 12
A resin plate was prepared under the same conditions as in Example 1 except that a monomer mixture consisting of 1 part by weight and 3 parts by weight of benzyl methyl maleate was used. This product was colorless and transparent, had a high refractive index and low dispersion (ν _D 48). The test results are shown in Table 1.

[0031]

Example 3 Instead of the monomer mixture used in Example 1,
15 parts by weight of triphenylvinylsilane, 10 parts by weight of diphenyldivinylsilane, 32 parts by weight of diallyl isophthalate, 2,2-bis (acryloxy-poly <4.2> ethoxy-phenyl) propane [Note: poly <4.2> ethoxy Represents a total of 4.2 mol of ethylene oxide.
Same below] 20 parts by weight, 20 parts by weight of bisphenol A diallyl carbonate and benzyl methyl maleate 3
A resin plate was prepared under the same conditions as in Example 1 except that a monomer mixture consisting of parts by weight was used. It was colorless and transparent, had a high refractive index, and had a low dispersion (ν _D 46). The test results are shown in Table 1.
It was shown to.

[0032]

Example 4 Instead of the monomer mixture used in Example 1,
30 parts by weight of triphenylvinylsilane, 43 parts by weight of diallyl isophthalate, 20 parts by weight of 2,2-bis (acryloxy-poly <4.2> ethoxy-phenyl) propane, 1,3,5-benzenetricarboxylic acid triallyl ester 4 1 part by weight and 3 parts by weight of benzyl methyl maleate were used as a radical polymerization initiator, and 2 parts by weight of dineopentyl purge carbonate and 2 parts by weight of t-butylperoxy-2-ethylhexanoate were used as radical polymerization initiators. And 1,1-bis (t-butylperoxy)
-1,3,3,5-Trimethylcyclohexane 1.5 parts by weight was added, and the temperature-time curve of the cast polymerization was 30 ° C. to 50 ° C. and the temperature was raised slowly from 5 ° C. to 50 ° C. To 65 ° C. in 1.5 hours, the temperature rises rapidly from 65 ° C. to 80 ° C. in 4 hours, and the temperature rises gradually from 80 ° C. to 95 ° C. in 1.5 hours. The temperature rises from 95 ° C to 110 ° C over 4 hours with a gentle slope, from 110 ° C to 120 ° C rises rapidly in 1 hour, and then continuously heated at 120 ° C for 2 hours. The polymerization was terminated. The subsequent heat treatment was carried out at 125 ° C. for 1 hour. Other procedures were the same as in Example 1, and a resin plate was prepared and tested. The results are shown in Table 1.

[0033]

EXAMPLE 5 Instead of the monomer mixture used in Example 4, 20 parts by weight of triphenylvinylsilane, 15 parts by weight of diphenyldivinylsilane, 38 parts by weight of diallyl isophthalate, 2,2-bis (acryloxy-poly <4 .2> ethoxy-phenyl) propane 20 parts by weight, phenylphenol allyl carbonate 5 parts by weight, and using a monomer mixture consisting of benzyl methyl maleate 2 parts by weight, the resin plate was prepared and tested under the same conditions as in Example 4 except for the above. did. The results are shown in Table 1.

[0034]

[Table 1]

[0035]

As described above, the present invention has a refractive index N _D
Not only in the vicinity of 1.59 to 1.60, but also in a high Abbe number ν _D (that is, low dispersion) and many other excellent properties. It is provided. That is, according to the present invention, by using triphenylvinylsilane and diphenyldivinylsilane as the monomer for improving the performance which brings about a high refractive index, diallyl isophthalate and diallyl terephthalate which are easily available and an optically homogeneous polymer are easily obtained. Is used as a main monomer, and a known third monomer is appropriately added to this to provide a method for efficiently producing a resin for a high refractive index lens under mild polymerization conditions.

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[Procedure amendment]

[Submission date] September 21, 1994

[Procedure Amendment 1]

[Document name to be amended] Statement

[Correction target item name] 0004

[Correction method] Change

[Correction content]

Based on such thinking, many studies have been conducted on the development of thermosetting resin for high refractive index lenses,
Many patent applications have been filed. Among them, what is currently regarded as important is one having a refractive index N _D in the vicinity of 1.57 to 1.60, which includes bisphenol A or a similar compound containing 2 or more halogens, especially bromine atoms. In particular, a high-refractive-index resin whose main component is a monomer having a skeleton obtained by adding 4 units. (Japanese Patent Publication No. 62-25162, Japanese Patent Publication No. 2-15841, Japanese Patent Publication No. 3)
-19521, Japanese Patent Publication No. 3-20721) A high refractive index resin obtained by mainly utilizing a reaction (urethane forming reaction) between an isocyanate compound and a hydroxyl compound or a thiol compound. (JP-A-57-136601, 57-136602, 5)
9-133211, 60-11513, 60-24
9101, 62-73201, 64-26622,
64-54021, JP-A-1-185501, 2-
153302)).

[Procedure Amendment 2]

[Document name to be amended] Statement

[Correction target item name] 0007

[Correction method] Change

[Correction content]

The above-mentioned techniques (1) and (2) satisfy almost all of these desirable requirements except that they have a quasi-high refractive index, whereas the technique (2) requires the cost of producing and purifying the monomer. The problem is that the resin is expensive and the impact resistance and light resistance of the obtained resin are insufficient, and in the case of, the technology has not been solidified yet and the operating conditions are severe, so the yield has reached a satisfactory point. The problem is not. Improved point not quasi high refractive index Shikae in therefore and techniques, if it was possible to increase the high refractive index (around N _D from 1.57 to 1.60), I say to give the most desirable method obtain. The present inventors have conducted extensive research to obtain the most desirable method, and arrived at the present invention.

[Procedure 3]

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Here, the synthetic methods of both silanes used in the present invention are listed. a) Synthetic method of triphenylvinylsilane: It can be synthesized by using the Grignard reaction. As an example, using sufficiently purified tetrahydrofuran as a solvent, vinylmagnesium bromide is allowed to act on triphenylchlorosilane or triphenylsilane, decomposed with a saturated aqueous solution of ammonium chloride, and then triphenylvinylsilane dissolved in tetrahydrofuran is recovered. Then, it was purified by vacuum distillation in the presence of a polymerization inhibitor and a trace amount of nitrogen gas. It is a white solid (a colorless transparent liquid when melted). (When triphenylsilane is used as the raw material, a small amount (for example, 10% or less) of the raw material substance may remain in the synthesized triphenylvinylsilane, but this does not substantially affect the performance of the lens resin of the present invention. Do not give.)

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[0028]

Example 1 A monomer mixture consisting of 10 parts by weight of triphenylvinylsilane, 70 parts by weight of diallyl isophthalate, 17 parts by weight of bisphenol S diallyl carbonate and 3 parts by weight of benzyl methyl maleate was added to 2- [2 as an ultraviolet absorber. -Hydroxy-5- (1,1,3,3
-Tetramethylbutyl) phenyl] benzotriazole (0.3 parts by weight) was added and dissolved, and t-butylperoxy-2-ethylhexanoate (2.5 parts by weight) and t-butylperoxy- Three
A space formed by adding 2.5 parts by weight of 5,5-trimethylhexanoate and dissolving it, and mixing this polymerization mixture with two surface-reinforced glass flat plate molds (distance: 2 mm) and a gasket made of an ethylene-butadiene copolymer. It was poured into the mixture at a warm temperature (50 ° C.) and cast polymerization was carried out.

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[0030]

Example 2 Instead of the monomer mixture used in Example 1,
8 parts by weight of triphenylvinylsilane, 8 parts by weight of diphenyldivinylsilane, 58 parts by weight of diallyl terephthalate, 2,2-bis (methacryloxy-poly <4.5> ethoxy-phenyl) propane [Note: poly <4.5> ethoxy is Represents a total of 4.5 mol of ethylene oxide.
A resin plate was prepared under the same conditions as in Example 1 except that a monomer mixture consisting of 15 parts by weight, 8 parts by weight of bisphenol S dimethacrylate and 3 parts by weight of benzyl methyl maleate was used. This product was colorless and transparent, had a high refractive index and low dispersion (ν _D 46). The test results are shown in Table 1.

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[0031]

Example 3 Instead of the monomer mixture used in Example 1,
15 parts by weight of triphenylvinylsilane 10 parts by weight of diphenyldivinylsilane, 40 parts by weight of diallyl isophthalate, 2,2-bis (methacryloxy-poly (4.3) ethoxy-phenyl) propane [Note: poly (4.3) ethoxy is It represents a total of 4.3 mol of ethylene oxide.
The same applies hereinafter] 17 parts by weight, 15 parts by weight of bisphenol S diallyl carbonate and benzyl methyl maleate 3
A resin plate was prepared under the same conditions as in Example 1 except that a monomer mixture consisting of parts by weight was used. It was colorless and transparent, had a high refractive index and low dispersion (ν _D 50). The test results are shown in Table 1.
It was shown to.

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[0032]

Example 4 Instead of the monomer mixture used in Example 1,
12 parts by weight of triphenylvinylsilane, 63 parts by weight of diallyl isophthalate, 2,2-bis (methacryloxy-
Radical polymerization using a monomer mixture consisting of 20 parts by weight of poly (4.3> ethoxy-phenyl) propane, 2 parts by weight of 1,3,5-benzenetricarboxylic acid triallyl ester and 3 parts by weight of benzyl methyl maleate. As an initiator, 2 parts by weight of dineopentyl purge carbonate, 2 parts by weight of t-butylperoxy-2-ethylhexanoate and 1,1-bis (t-butylperoxy)
-1,3,3,5-Trimethylcyclohexane 1.5 parts by weight was added, and the temperature-time curve of the cast polymerization was 30 ° C. to 50 ° C. and the temperature was raised slowly from 5 ° C. to 50 ° C. To 65 ° C. in 1.5 hours, the temperature rises rapidly from 65 ° C. to 80 ° C. in 4 hours, and the temperature rises gradually from 80 ° C. to 95 ° C. in 1.5 hours. The temperature rises from 95 ° C to 110 ° C over 4 hours with a gentle slope, from 110 ° C to 120 ° C rises rapidly in 1 hour, and then continuously heated at 120 ° C for 2 hours. The polymerization was terminated. The subsequent heat treatment was carried out at 125 ° C. for 1 hour. Other procedures were the same as in Example 1, and a resin plate was prepared and tested. The results are shown in Table 1.

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[0033]

Example 5 Instead of the monomer mixture used in Example 4, 10 parts by weight of triphenylvinylsilane, 8 parts by weight of diphenyldivinylsilane, 50 parts by weight of diallyl isophthalate, 2,2-bis (methacryloxy-poly (4) .3> same as in Example 4 except that a monomer mixture consisting of 20 parts by weight of ethoxy-phenyl) propane, 8 parts by weight of bis (2-hydroxyethoxy) bisphenol S dimethacrylate and 4 parts by weight of benzylmethyl maleate was used. A resin plate was made under the conditions and tested. The results are shown in Table 1.

[Procedure Amendment 9]

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[Correction target item name] 0035

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[0035]

As described above, the present invention has a refractive index N _D
Is not only high around 1.57 to 1.60, but also has a high Abbe number ν _D (that is, low dispersion) and many other excellent properties. It is provided. That is, according to the present invention, by using triphenylvinylsilane and diphenyldivinylsilane as the monomer for improving the performance which brings about a high refractive index, diallyl isophthalate and diallyl terephthalate which are easily available and an optically homogeneous polymer are easily obtained. Is used as a main monomer, and a known third monomer is appropriately added to this to provide a method for efficiently producing a resin for a high refractive index lens under mild polymerization conditions.

[Procedure Amendment 10]

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[Correction target item name] 0034

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[0034]

[Table 1]

Claims (2)

[Claims] 1. One or more members of the group consisting of triphenylvinylsilane and diphenyldivinylsilane and one or more members of a radical-polymerizable monomer having a homopolymer having a refractive index of 1.55 or more. A method for producing a resin for a high refractive index lens, which comprises polymerizing. 2. A first monomer, 3 to 40% by weight, preferably 7 to 30% by weight, of one or two members selected from the group consisting of triphenylvinylsilane and diphenyldivinylsilane, and diallyliso as the second monomer. 2 of 1 or 2 of the group consisting of phthalate and diallyl terephthalate
0 to 70% by weight, and as the third monomer, a homopolymer having a refractive index of 1.55 or more and one or more other radically polymerizable monomers are mixed in an amount of 0 to 40% by weight, and then mixed. A method for producing a resin for a high refractive index lens, which comprises polymerizing.